JPS6017377B2 - Method for producing polymerizable organopolysiloxane - Google Patents
Method for producing polymerizable organopolysiloxaneInfo
- Publication number
- JPS6017377B2 JPS6017377B2 JP54097587A JP9758779A JPS6017377B2 JP S6017377 B2 JPS6017377 B2 JP S6017377B2 JP 54097587 A JP54097587 A JP 54097587A JP 9758779 A JP9758779 A JP 9758779A JP S6017377 B2 JPS6017377 B2 JP S6017377B2
- Authority
- JP
- Japan
- Prior art keywords
- mol
- methacrylic acid
- reaction
- acrylic acid
- 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
- 229920001296 polysiloxane Polymers 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 20
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- -1 alkali metal salt Chemical class 0.000 claims description 9
- 239000004593 Epoxy Substances 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 description 11
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- SONHXMAHPHADTF-UHFFFAOYSA-M sodium;2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O SONHXMAHPHADTF-UHFFFAOYSA-M 0.000 description 3
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- LKWVKJXZKSOZIW-UHFFFAOYSA-N 2,5-dibutylbenzene-1,4-diol Chemical compound CCCCC1=CC(O)=C(CCCC)C=C1O LKWVKJXZKSOZIW-UHFFFAOYSA-N 0.000 description 1
- LZFZQYNTEZSWCP-UHFFFAOYSA-N 2,6-dibutyl-4-methylphenol Chemical compound CCCCC1=CC(C)=CC(CCCC)=C1O LZFZQYNTEZSWCP-UHFFFAOYSA-N 0.000 description 1
- VAPQAGMSICPBKJ-UHFFFAOYSA-N 2-nitroacridine Chemical compound C1=CC=CC2=CC3=CC([N+](=O)[O-])=CC=C3N=C21 VAPQAGMSICPBKJ-UHFFFAOYSA-N 0.000 description 1
- WQBCQEDMLHHOMQ-UHFFFAOYSA-N 4-methoxycyclohexa-1,5-diene-1,4-diol Chemical compound COC1(O)CC=C(O)C=C1 WQBCQEDMLHHOMQ-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 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 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Landscapes
- Macromonomer-Based Addition Polymer (AREA)
- Silicon Polymers (AREA)
Description
【発明の詳細な説明】
本発明は重合性オルガノポリシロキサン、詳しくは一般
式〔式中、ＲＩは一価炭化水素基、Ｒ２は水素原子また
はメチル基、Ｂは一価炭化水素基または式（ここにＲＩ
およびＲ２は前記と同じ意味である）で示される基を表
わす。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a polymerizable organopolysiloxane, specifically a compound of the general formula [where RI is a monovalent hydrocarbon group, R2 is a hydrogen atom or a methyl group, and B is a monovalent hydrocarbon group or a compound of the formula ( R.I. here
and R2 have the same meanings as above).
ａは０，１または２、ｍは１〜４の整数、ｎは１〜５の
整数である。〕で示されるオルガノポリシロキサンの製
造方法に関するものである。上記した一般式（１）で示
される重合性オルガノポリシロキサンは公知であり、従
来このオルガノポリシロキサンの製造方法としては、例
えば一般式で示される基を表す。a is 0, 1 or 2, m is an integer of 1 to 4, and n is an integer of 1 to 5. ] The present invention relates to a method for producing an organopolysiloxane shown in the following. The polymerizable organopolysiloxane represented by the above general formula (1) is known, and conventional methods for producing this organopolysiloxane include, for example, a group represented by the general formula.
ａは０，１または２、ｐは１〜４の整数、ｑは０〜５の
整数である）で示されるェボキシ結合含有オルガノシラ
ンまたはシロキサンとアクリル酸またはメタクリル酸と
を単に混合したのち加熱し反応を行う方法あるいは両者
を水酸化ナトリウム、水酸化リチウムもしくは水酸化カ
リウムなどのようなアルカリ性物質の存在下で必要に応
じて加熱し反応させる方法が知られている。しかしなが
ら前者の方法には、反応速度が遅く、かつ反応を良好に
進行させようとする場合には反応温度を１３０〜１５ぴ
Ｃの高温とする必要があり、このような高温は副生成物
が生成し収率が低下するため上記したような一般式（１
）で示される重合性オルガノシロキサンの製造には不適
当であるという不利があった。(a is 0, 1 or 2, p is an integer of 1 to 4, and q is an integer of 0 to 5) is simply mixed with an eboxy bond-containing organosilane or siloxane and acrylic acid or methacrylic acid, and then heated. A method for carrying out the reaction or a method for reacting the two by heating as necessary in the presence of an alkaline substance such as sodium hydroxide, lithium hydroxide, or potassium hydroxide is known. However, in the former method, the reaction rate is slow, and if you want the reaction to proceed well, it is necessary to set the reaction temperature to a high temperature of 130 to 15 picoC. Since the above-mentioned general formula (1
) had the disadvantage of being unsuitable for producing polymerizable organosiloxanes.
また、後者のアルカリ性物質を使用する方法は、該反応
を７０〜１００００の比較的低い反応温度で行わせるこ
とができるが、これには一般に反応に要する時間が長く
なり、しかも副生成物が多量に生成し、たとえ分子蒸留
などの処理を行って精製しても最終目的物を高純度、高
収率で得ることが困難であるといいう欠点があった。In addition, in the latter method of using an alkaline substance, the reaction can be carried out at a relatively low reaction temperature of 70 to 10,000 °C, but this generally requires a long reaction time and also produces a large amount of by-products. The disadvantage is that it is difficult to obtain the final target product with high purity and high yield even if it is purified by treatments such as molecular distillation.
本発明は上記したような従来方法における不利および欠
点を除去した上記一般式（１）で示される重合性オルガ
ノポリシロキサンの新規な製造方法を提供しようとする
ものであって、これは一般式で示されるェポキシ結合含
有オルガノポリシロキサンとアクリル酸またはメタクリ
ル酸とをアクリル酸またはメタクリル酸のアルカリ金属
塩の存在下で反応させることを特徴とするものである。The present invention aims to provide a new method for producing a polymerizable organopolysiloxane represented by the general formula (1), which eliminates the disadvantages and drawbacks of the conventional methods as described above. It is characterized in that the epoxy bond-containing organopolysiloxane shown above is reacted with acrylic acid or methacrylic acid in the presence of an alkali metal salt of acrylic acid or methacrylic acid.
含有オルガノポリシロキサンとアクリル酸またはメタク
リル酸とを反応させ上記した一般式（１）で示される重
合性オルガノポリシロキサンを製造する方法について鋭
意研究を重ねた結果、これには該反応をアクリル酸また
はメタクリル酸のアルカリ金属塩の存在下で行うことが
きわめて有効であることを見出し本発明を完成したもの
であって、これによれば、副生成物の生成もなく、また
高度な精製技術を採用することなく、高純度、高収率で
上記した一般式（１）で示される重合性オルガノポリシ
ロキサンを製造することができ、さらに前記反応を行う
にあたっては有機溶媒を使用する必要が全くないという
顕著な効果が与えられる。つぎに本発明方法をさらに詳
細に説明する。As a result of extensive research into a method for producing the polymerizable organopolysiloxane represented by the general formula (1) above by reacting the containing organopolysiloxane with acrylic acid or methacrylic acid, we found that They discovered that it is extremely effective to carry out the process in the presence of an alkali metal salt of methacrylic acid, and completed the present invention.According to this, there is no generation of by-products, and advanced purification technology is adopted. The polymerizable organopolysiloxane represented by the above general formula (1) can be produced with high purity and high yield without any reaction, and furthermore, there is no need to use an organic solvent in carrying out the reaction. A noticeable effect is given. Next, the method of the present invention will be explained in more detail.
まず、本発明において始発原料として使用されるェポキ
シ結合含有オルガノポリシロキサンは上託した一般式（
０）で示されるものであって、該式中ＲＩは一価炭化水
素基を表わし、これには例えばメチル基、エチル基、プ
ロピル基あるいはブチル基などのアルキル基、シクロベ
ンチル基あるいはシクロヘキシル基などのシクロアルキ
ル基、フェニル基、トリル基あるいはキシリル基などの
アリール基、またはこれらの基の水素原子が部分的にハ
ロゲン原子などで置換された基などがあげられる。なお
、本発明においては、上記ＲＩが炭素原子数１〜４のア
ルキル基またはフェニル基から選択される基であること
が反応性あるいは収率などの点から望ましい。First, the epoxy bond-containing organopolysiloxane used as a starting material in the present invention has the general formula (
0), in which RI represents a monovalent hydrocarbon group, which includes, for example, an alkyl group such as a methyl group, an ethyl group, a propyl group or a butyl group, and a cyclobentyl group or a cyclohexyl group. Examples include aryl groups such as cycloalkyl groups, phenyl groups, tolyl groups, and xylyl groups, and groups in which the hydrogen atoms of these groups are partially substituted with halogen atoms. In the present invention, it is desirable from the viewpoint of reactivity or yield that the RI is a group selected from an alkyl group having 1 to 4 carbon atoms or a phenyl group.
また、Ａは一価炭化水素基または上託した式（ｉｉ｝で
示される基を表わす。Further, A represents a monovalent hydrocarbon group or a group represented by the specified formula (ii).
ａ，ｍおよびｎは前述の通りである。a, m and n are as described above.
このようなェポキシ結合含有オルガノボリシロキサンは
従来から知られている方法により合成することができ、
該オルガノポリシロキサンとしては具体的には下記に示
すような化合物があげられる。Such epoxy bond-containing organoborisiloxanes can be synthesized by conventionally known methods,
Specific examples of the organopolysiloxane include the compounds shown below.
つぎに、本発明において、使用されるアクリル酸または
メタクリル酸のアルカリ金属塩としては例えば下記のよ
うな化合物があげられる。Next, examples of the alkali metal salts of acrylic acid or methacrylic acid used in the present invention include the following compounds.
本発明の方法は、上記した一般式（Ｄ）で示されるェポ
キシ結合含有オルガノポリシロキサンとアクリル酸また
はメタクリル酸とを、アクリル酸またはメタクリル酸の
アルカリ金属塩の存在下で反応させるのであるが、始発
原料である両者の使用割合は、一般式（０）で示される
ポリシロキサン中のェポキシ結合１個に対してアクリル
酸またはメタクリル酸を１．０〜３．０モルの範囲で使
用することがよく、とくにアクリル酸またはメタクリル
酸の使用量を１．３モル以上とすれば反応時間を短縮す
ることができるとともに未反応のポリシロキサンの残存
がみられず好都合である。The method of the present invention involves reacting the epoxy bond-containing organopolysiloxane represented by the general formula (D) with acrylic acid or methacrylic acid in the presence of an alkali metal salt of acrylic acid or methacrylic acid. The ratio of the two starting materials used is 1.0 to 3.0 moles of acrylic acid or methacrylic acid per epoxy bond in the polysiloxane represented by general formula (0). In particular, if the amount of acrylic acid or methacrylic acid used is 1.3 mol or more, the reaction time can be shortened and no unreacted polysiloxane remains, which is advantageous.
該アクリル酸またはメタクリル酸の使用量が１．０モル
味満では反応を完結するのに要する時間が長くなるほか
味反応のポリシロキサンが残り目的物を高純度で得るこ
とが困難となり、他方、３．０モル以上使用してもとく
に前記したような問題はないが経済的に不利となる。ま
た、アクリル酸またはメタクリル酸のアルカＩＪ金属塩
の使用量は、一般式（０）で示されるポリシロキサン中
のヱポキシ結合１個に対して０．０５〜０．２０モルの
範囲で使用することが好ましい。If the amount of acrylic acid or methacrylic acid used is 1.0 mol, the time required to complete the reaction will be longer, and the polysiloxane of the taste reaction will remain, making it difficult to obtain the target product with high purity. If 3.0 mol or more is used, there is no particular problem as mentioned above, but it is economically disadvantageous. Further, the amount of the alkali IJ metal salt of acrylic acid or methacrylic acid to be used is within the range of 0.05 to 0.20 mol per epoxy bond in the polysiloxane represented by general formula (0). is preferred.
さらに反応温度については７０〜１３０００、好ましく
は９０〜１１０ｑｏの範囲とすることがよい。なお、本
発明においては重合禁止剤を使用することが好ましく、
具体的にはハイドロキノン、メトキシハイドロキノン、
４ーメトキシフエノ−ル、２，６ージ−ｔｅれ−ブチル
ー４−クレゾール、２，５−ジー企てｔ−ブチルハイド
ロキノンなどの一般に重合禁止剤として知られているも
のを使用することができ、この重合禁止剤の使用量はア
クリル酸またはメタクリル酸１モルに対して０．００１
〜０．１モルは範囲とすれば充分である。他方、本発明
方法を実施するに際しては、溶媒とくにｎーヘキサン、
ベンゼン、トルエンあるいはキシレンなどの非樋性溶媒
の使用は禁物であり、これらを使用した場合には収率の
低下あるいは不純物を増加させるほか、系全体をゲル化
させるおそれが生じる。本発明方法で得られる上記一股
式（１）で示される重合性オルガノポリシロキサンとし
ては例えば下記に示すようなものがあげられる。Furthermore, the reaction temperature is preferably in the range of 70 to 13,000 qo, preferably 90 to 110 qo. In addition, in the present invention, it is preferable to use a polymerization inhibitor,
Specifically, hydroquinone, methoxyhydroquinone,
Generally known polymerization inhibitors such as 4-methoxyphenol, 2,6-di-butyl-4-cresol, and 2,5-di-butylhydroquinone can be used; The amount of polymerization inhibitor used is 0.001 per mole of acrylic acid or methacrylic acid.
A range of 0.1 mol to 0.1 mol is sufficient. On the other hand, when carrying out the method of the present invention, solvents, especially n-hexane,
The use of non-polluting solvents such as benzene, toluene, or xylene is prohibited; if they are used, the yield may decrease or impurities may increase, and the entire system may gel. Examples of the polymerizable organopolysiloxane represented by the above-mentioned single-pronged formula (1) obtained by the method of the present invention include those shown below.
上述のようにして得られる一般式（１）で示される重合
性オルガノポリシロキサンは反応性中間体として各種の
共重合体の製造に応用することができる。The polymerizable organopolysiloxane represented by the general formula (1) obtained as described above can be applied as a reactive intermediate to the production of various copolymers.
例えば単独もしくは、アクリル酸、メタクリル酸あるい
はこれらの譲導体と公知の方法に準じて重合させること
ができ、このようにして得られる重合体はコーティング
剤、サィジング剤、縦水剤、雛形剤、隣脂改質剤あるい
は潤滑剤などに広く応用可能である。つぎに本発明の実
施例および比較例をあげる。For example, it can be polymerized alone or with acrylic acid, methacrylic acid, or derivatives thereof according to known methods. It can be widely applied as a fat modifier or lubricant. Next, examples of the present invention and comparative examples will be given.
実施例 １内容積１そのセパラフラスコに、メタクリル
酸１７滋（２モル）、メタクリル酸ナトリウム１６．彼
（０．１５モル）および４ーメトキシハイドロキノン１
８．舷（０．１５モル）を仕込み、内温が９０℃になる
まで加熱し、ついで式で示されるシロキサン３５蟹（１
モル）を滴下した。Example 1 Inner volume: 1 Into a separate flask, 17 g (2 mol) of methacrylic acid and 16 g of sodium methacrylate were added. he (0.15 mol) and 4-methoxyhydroquinone 1
8. Pour siloxane (0.15 mol) and heat until the internal temperature reaches 90°C, then add siloxane 35 crab (1
mol) was added dropwise.
滴下終了後、温度９０〜９５℃で２ｑ時間反応させたと
ころ、反応生成物が得られた。つぎに上記で得た反応生
成物を溶剤で稀釈したのちアルカリ洗浄し、ついで重合
禁止剤および溶剤を除去したところ、粘度３０．次Ｓ（
２５℃）、屈折率１．４３８０（２５℃）の下記式で示
される重合性オルガ／ポリシロキサンが得られ、このも
のの純度（ガスクロマトグラフイ‐分析による。After completion of the dropwise addition, reaction was carried out at a temperature of 90 to 95° C. for 2 q hours, and a reaction product was obtained. Next, the reaction product obtained above was diluted with a solvent, washed with alkali, and then the polymerization inhibitor and solvent were removed, and the viscosity was 30. Next S (
A polymerizable olga/polysiloxane having a refractive index of 1.4380 (at 25°C) and having a refractive index of 1.4380 (at 25°C) was obtained, and its purity was determined by gas chromatography analysis.
以下同様）は職．４％であり、収率は８７．５％であっ
た。実施例 ２内容銭１そのセパラフラスコに、アクリ
ル酸１３雌（１．８モル）、アクリル酸カリウム１１ｇ
（０．１０モル）およびハイドロキノン５．鴇（０．０
５モル）を仕込み内温が８６０になるまで加熱し、つい
で式で示されるシロキサン２４滋（１モル）を滴下した
。) is a job. 4%, and the yield was 87.5%. Example 2 Contents 1 In the separate flask, acrylic acid 13 (1.8 mol), potassium acrylate 11 g
(0.10 mol) and hydroquinone5. Toshi (0.0
5 mol) was charged and heated until the internal temperature reached 860, and then 24 g (1 mol) of siloxane represented by the formula was added dropwise.
滴下終了後温度８５〜９０℃で２虫時間反応させたとこ
ろ、反応生成物が得られた。つぎに上記で得られた生成
物を実施例１と同様の方法で処理したところ、粘度２１
．枕Ｓ（２５℃）、屈折率１．４３７０（２５℃）の下
記式で示される重合性オルガノポリシロキサンが得られ
、このものの純度は９８．６％であり、収率は８６．４
％であった。After the dropwise addition was completed, the reaction was carried out at a temperature of 85 to 90° C. for 2 hours, and a reaction product was obtained. Next, the product obtained above was treated in the same manner as in Example 1, and the viscosity was 21.
．． A polymerizable organopolysiloxane having a refractive index of 1.4370 (25°C) and having a refractive index of 1.4370 (25°C) was obtained, the purity of which was 98.6%, and the yield was 86.4.
%Met.
実施例 ３内容積１そのセパラフラスコにメタクリル酸
４３咳（４．０モル）、メタクリル酸ナトリウム２を（
０．２５モル）および４−メトキシフエノール３７．衣
（０．３モル）を仕込み、内温が９０℃になるまで加熱
し、ついで式で示されるシロキサン３６雄（１モル）を
滴下した。Example 3 Inner volume 1 In a separate flask, 43 methacrylic acid (4.0 mol) and 2 sodium methacrylate (
0.25 mol) and 4-methoxyphenol 37. A batter (0.3 mol) was charged and heated until the internal temperature reached 90°C, and then siloxane 36 (1 mol) represented by the formula was added dropwise.
滴下終了後、温度９５ｑｏで２幼時間反応させたところ
、反応生成物が得られた。After the dropwise addition was completed, a reaction product was obtained by allowing the mixture to react at a temperature of 95 qo for 2 hours.
つぎに上記で得た生成物を実施例１と同様の方法で処理
したところ、粘度２１次Ｓ（２５℃）、屈折率１．４６
７０（２ず０）の下記分子式で示される重合性オルガノ
ポリシロキサンが得られ、このものの純度は９８．７％
であり、収率は８９．４％であった。Next, when the product obtained above was treated in the same manner as in Example 1, it had a viscosity of 21st order S (25°C) and a refractive index of 1.46.
A polymerizable organopolysiloxane having the following molecular formula of 70(2z0) was obtained, and the purity of this product was 98.7%.
The yield was 89.4%.
実施例 ４内容積１そのセパラフラスコに、メタクリル
酸１７後（２．０モル）、メタクリル酸ナトリウ，ム１
６．彼（０．１５モル）および４ーメトキシフエニール
１８．鍵（０．１５モル）を仕込み、内温が９０ｏｏに
なるまで加熱し、ついで式で示されるシロキサン３３舷
（１モル）を滴下した。Example 4 Inner volume 1 In a separate flask, methacrylic acid 17 (2.0 mol), sodium methacrylate, 1
6. He (0.15 mol) and 4-methoxyphenyl 18. A key (0.15 mol) was charged and heated until the internal temperature reached 90 oo, and then 33 molars (1 mol) of siloxane represented by the formula were added dropwise.
滴下終了後、温度９０〜９５ｑｏで２曲時間反応させた
ところ、反応生成物が得られた。After completion of the dropwise addition, reaction was carried out at a temperature of 90 to 95 qo for 2 hours, and a reaction product was obtained.
つぎに上記で得た生成物を実施例１と同様の方法で処理
したところ、粘度２５．７ｃＳ（２５００）、屈折率１
．４３６９（２５ｑｏ）の下記分子式で示される重合性
オルガノポリシロキサンが得られ、このものの純度は９
８．９％であり、収率は別８７％であった。Next, when the product obtained above was treated in the same manner as in Example 1, it had a viscosity of 25.7 cS (2500) and a refractive index of 1.
．． A polymerizable organopolysiloxane having the following molecular formula of 4369 (25qo) was obtained, and the purity of this product was 9.
The yield was 8.9%, and the yield was another 87%.
比較例内容積ＩＺのセパラフラスコに、メタクリル酸】
７滋（２０モル）、水酸化ナトリウム能（０．１５モル
）および４ーメトキシフエノール１８．股（０．１５モ
ル）を仕込み、内温が９０ｑｏになるまで加熱し、つい
で式で示されるシロキサン３３６ｇ（１モル）を滴下し
た。Comparative example: methacrylic acid in a Separa flask with internal volume IZ]
7. (20 mol), sodium hydroxide capacity (0.15 mol) and 4-methoxyphenol 18. The mixture was heated until the internal temperature reached 90 qo, and then 336 g (1 mol) of siloxane represented by the formula was added dropwise.
Claims (1)
アクリル酸またはメタクリル酸とを、アクリル酸または
メタクリル酸のアルカリ金属塩の存在下で反応させるこ
とを特徴とする、一般式▲数式、化学式、表等がありま
す▼で示される重合性オルガノポリシロキサンの製造方
法。 ▲数式、化学式、表等があります▼[Claims] 1. Epoxy bond-containing organopolysiloxane represented by the general formula ▲ Numerical formula, chemical formula, table, etc. ▼ and acrylic acid or methacrylic acid in the presence of an alkali metal salt of acrylic acid or methacrylic acid. A method for producing polymerizable organopolysiloxane represented by the general formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼, which is characterized by a reaction. ▲Contains mathematical formulas, chemical formulas, tables, etc.▼
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP54097587A JPS6017377B2 (en) | 1979-07-31 | 1979-07-31 | Method for producing polymerizable organopolysiloxane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP54097587A JPS6017377B2 (en) | 1979-07-31 | 1979-07-31 | Method for producing polymerizable organopolysiloxane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5622325A JPS5622325A (en) | 1981-03-02 |
| JPS6017377B2 true JPS6017377B2 (en) | 1985-05-02 |
Family
ID=14196361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP54097587A Expired JPS6017377B2 (en) | 1979-07-31 | 1979-07-31 | Method for producing polymerizable organopolysiloxane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6017377B2 (en) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4576999A (en) * | 1982-05-06 | 1986-03-18 | General Electric Company | Ultraviolet radiation-curable silicone release compositions with epoxy and/or acrylic functionality |
| KR100749304B1 (en) * | 2000-08-28 | 2007-08-14 | 디시이 아프릴리스, 인코포레이티드 | Holographic recording medium containing multifunctional epoxy monomer capable of carrying out cationic polymerization |
| JP4720072B2 (en) * | 2003-07-01 | 2011-07-13 | 東レ株式会社 | Method for purifying silicone agent and silicone agent |
| JP4507580B2 (en) * | 2003-12-10 | 2010-07-21 | 東レ株式会社 | Method for producing silicone compound and silicone agent |
| EP1719776B1 (en) | 2004-02-27 | 2013-10-09 | Toray Industries, Inc. | Process for producing a silicone compound |
| JP4882241B2 (en) * | 2004-02-27 | 2012-02-22 | 東レ株式会社 | Method for producing silicone compound |
| US8053539B2 (en) * | 2006-06-30 | 2011-11-08 | Johnson & Johnson Vision Care Inc. | Siloxanyl materials for molded plastics |
| US20080081850A1 (en) * | 2006-09-29 | 2008-04-03 | Kazuhiko Fujisawa | Process for producing hydrolysis-resistant silicone compounds |
| US8080622B2 (en) | 2007-06-29 | 2011-12-20 | Johnson & Johnson Vision Care, Inc. | Soluble silicone prepolymers |
| JP5402934B2 (en) * | 2008-08-28 | 2014-01-29 | 日油株式会社 | Silicone monomer, its production method and use |
| EP2388281B1 (en) * | 2009-01-19 | 2013-11-06 | NOF Corporation | Silicone monomer |
| CN102482424B (en) * | 2009-09-02 | 2015-06-10 | 莫门蒂夫性能材料股份有限公司 | Silicone modified fatty acids, method of preparation and usage thereof |
| JP6800131B2 (en) | 2017-11-29 | 2020-12-16 | 信越化学工業株式会社 | Siloxane compound and its manufacturing method |
| JP7145122B2 (en) | 2019-06-06 | 2022-09-30 | 信越化学工業株式会社 | Siloxane and its manufacturing method |
| JP7324170B2 (en) * | 2020-04-02 | 2023-08-09 | 信越化学工業株式会社 | Method for producing silicone compound |
| JP7483649B2 (en) | 2021-03-17 | 2024-05-15 | 信越化学工業株式会社 | Siloxane compound and its manufacturing method |
| JP7411598B2 (en) | 2021-03-17 | 2024-01-11 | 信越化学工業株式会社 | Siloxane compound and its manufacturing method |
-
1979
- 1979-07-31 JP JP54097587A patent/JPS6017377B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5622325A (en) | 1981-03-02 |
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