JPH10170874A - Plastic moldings - Google Patents
Plastic moldingsInfo
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- JPH10170874A JPH10170874A JP32667496A JP32667496A JPH10170874A JP H10170874 A JPH10170874 A JP H10170874A JP 32667496 A JP32667496 A JP 32667496A JP 32667496 A JP32667496 A JP 32667496A JP H10170874 A JPH10170874 A JP H10170874A
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- molded article
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Abstract
(57)【要約】
【課題】高い透明性及び酸素透過性、良好な力学特性を
有するプラスチック成形品を提供する。
【解決手段】下記一般式（Ｉ）で示されるアミン化合物
を重合して得られることを特徴とするプラスチック成形
品。
【化１】
（Ｒ1 は水素原子またはメチル基であり、Ｒ2 は水素原
子、アルキル基、又はアリール基を示す。ｎは１〜１０
の整数、ｍは１〜６、ａ，ｂ、ｃはそれぞれが互いに０
〜２０の整数、ｄは０〜２００の整数、ｅは１または２
の整数である。Ａ，Ｂはそれぞれ互いに独立に、Ｃ１〜
Ｃ５のアルキル基、フェニル基、およびフルオロアルキ
ル基から選ばれる。）[PROBLEMS] To provide a plastic molded product having high transparency and oxygen permeability and good mechanical properties. A plastic molded article obtained by polymerizing an amine compound represented by the following general formula (I). Embedded image (R 1 is a hydrogen atom or a methyl group, and R 2 is a hydrogen atom, an alkyl group, or an aryl group. N is 1 to 10
M is 1 to 6, and a, b and c are each 0
An integer of 0 to 20, d is an integer of 0 to 200, e is 1 or 2
Is an integer. A and B are each independently C1-
It is selected from a C5 alkyl group, a phenyl group, and a fluoroalkyl group. )
Description
【０００１】[0001]
【発明の属する技術分野】本発明は新規なポリマーから
成るプラスチック成形品に関し、透明性、酸素透過性に
優れると共に良好な力学的特性を併せ持つプラスチック
成形品として、例えばコンタクトレンズ、眼内レンズな
どの眼用レンズに好適に用いられるものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a plastic molded product made of a novel polymer, which is excellent in transparency and oxygen permeability and has good mechanical properties, such as contact lenses and intraocular lenses. It is suitably used for ophthalmic lenses.
【０００２】[0002]
【従来の技術】近年酸素透過性を有するプラスチック成
形品としてトリス（トリメチルシロキシ）シリルプロピ
ルメタクリレートなどのシリル置換メタクリレートや変
性ポリシロキサンを一成分とするポリマーが開発され利
用されている（特開昭６０−１４２３２４号、特開昭５
４−２４０４７号）。2. Description of the Related Art In recent years, as a plastic molded article having oxygen permeability, a polymer containing one component of a silyl-substituted methacrylate such as tris (trimethylsiloxy) silylpropyl methacrylate and a modified polysiloxane has been developed and used (Japanese Patent Application Laid-Open No. Sho 60/1985). No. 142324, JP-A-5
No. 4-24047).
【０００３】しかしながらこれらのモノマー（マクロマ
ー）からなるポリマーには、対衝撃性に劣る等の物性上
の欠点を有している。また、現在得られているポリマー
は十分な酸素透過性を有しておらず、さらに高い酸素透
過性を有する素材が望まれている。However, polymers comprising these monomers (macromers) have drawbacks in physical properties such as poor impact resistance. Further, currently available polymers do not have sufficient oxygen permeability, and materials having even higher oxygen permeability are desired.
【０００４】[0004]
【発明が解決しようとする課題】本発明は、前記従来技
術の欠点を解決しようとするものであり、高い透明性、
高い酸素透過性を有し、かつ、力学的特性にも優れたプ
ラスチック成形品を提供することを目的とする。SUMMARY OF THE INVENTION The present invention is to solve the above-mentioned drawbacks of the prior art, and has high transparency,
An object of the present invention is to provide a plastic molded product having high oxygen permeability and excellent mechanical properties.
【０００５】[0005]
【課題を解決するための手段】本発明者は、上記目的を
達成するため鋭意検討を重ね、特定の単量体を構成成分
とする重合体を構成成分とするプラスチック成形品が、
高い透明性および酸素透過性、良好な力学的特性を有す
ることを見出し、本発明に至った。Means for Solving the Problems The present inventors have conducted intensive studies to achieve the above object, and have obtained a plastic molded article containing a polymer containing a specific monomer as a component.
The inventors have found that they have high transparency and oxygen permeability and good mechanical properties, and have led to the present invention.
【０００６】[0006]
【発明の実施の形態】即ち本発明は、下記一般式（Ｉ）
で示されるアミン化合物を重合して得られることを特徴
とするプラスチック成形品に関する。DETAILED DESCRIPTION OF THE INVENTION That is, the present invention provides a compound represented by the following general formula (I):
A plastic molded article obtained by polymerizing the amine compound represented by
【０００７】[0007]
【化２】 （Ｒ1 は水素原子またはメチル基であり、Ｒ2 は水素原
子、アルキル基、又はアリール基を示す。ｎは１〜１０
の整数、ｍは１〜６、ａ，ｂ、ｃはそれぞれが互いに０
〜２０の整数、ｄは０〜２００の整数、ｅは１または２
の整数である。Ａ，Ｂはそれぞれ互いに独立に、Ｃ１〜
Ｃ５のアルキル基、フェニル基、およびフルオロアルキ
ル基から選ばれる。） 本発明のプラスチック成形品は、前記一般式(I) で表わ
される化合物を重合成分の少なくとも１種として得られ
るポリマーからなる。Embedded image (R 1 is a hydrogen atom or a methyl group, and R 2 is a hydrogen atom, an alkyl group, or an aryl group. N is 1 to 10
M is 1 to 6, and a, b and c are each 0
An integer of 0 to 20, d is an integer of 0 to 200, e is 1 or 2
Is an integer. A and B are each independently C1-
It is selected from a C5 alkyl group, a phenyl group, and a fluoroalkyl group. The plastic molded article of the present invention comprises a polymer obtained by using the compound represented by the general formula (I) as at least one kind of polymerization component.
【０００８】[0008]
【化３】 （Ｒ1 は水素原子またはメチル基であり、Ｒ2 は水素原
子、アルキル基、又はアリール基を示す。ｎは１〜１０
の整数、ｍは１〜６、ａ，ｂ、ｃはそれぞれが互いに０
〜２０の整数、ｄは０〜２００の整数、ｅは１または２
の整数である。Ａ，Ｂはそれぞれ互いに独立に、Ｃ１〜
Ｃ５のアルキル基、フェニル基、およびフルオロアルキ
ル基から選ばれる。） Ｒ1 は水素原子またはメチル基であるが、特にメチル基
が好ましい。Ａ、Ｂにおいて、アルキル基としてはメチ
ル基、エチル基が好ましく、また、フルオロアルキル基
としてはトリフルオロメチル基、ペンタフルオロエチル
基が好ましい。Ａとしては、物性のバランスの点でメチ
ル基が好ましい。d は0 〜200 の整数であるが、好まし
くは0 〜50、さらに好ましくは0 〜10、さらには優れた
物性を示す点で０であることが好ましい。a 、b 、c は
それぞれが互いに独立に0 〜20の整数であるが、好まし
くはa 、b 、c がそれぞれが互いに独立に0 〜5 の整
数、さらに好ましくはa=b=c=1 である。ｍは１〜６の整
数であるが、中でも原料が入手しやすいという点でｍは
３であることが好ましい。また、Ｒ2 は、水素原子、ア
ルキル基、アリール基から選ばれるが、アルキル基とし
ては、メチル基、エチル基等が好ましく、また、アリー
ル基としては、フェニル基などが好ましい。Embedded image (R 1 is a hydrogen atom or a methyl group, and R 2 is a hydrogen atom, an alkyl group, or an aryl group. N is 1 to 10
M is 1 to 6, and a, b and c are each 0
An integer of 0 to 20, d is an integer of 0 to 200, e is 1 or 2
Is an integer. A and B are each independently C1-
It is selected from a C5 alkyl group, a phenyl group, and a fluoroalkyl group. R 1 is a hydrogen atom or a methyl group, and particularly preferably a methyl group. In A and B, the alkyl group is preferably a methyl group or an ethyl group, and the fluoroalkyl group is preferably a trifluoromethyl group or a pentafluoroethyl group. A is preferably a methyl group from the viewpoint of balance of physical properties. d is an integer of 0 to 200, preferably 0 to 50, more preferably 0 to 10, and even more preferably 0 in view of excellent physical properties. a, b, and c are each independently an integer of 0 to 20, preferably a, b, and c are each independently an integer of 0 to 5, more preferably a = b = c = 1. is there. m is an integer of 1 to 6, and among these, m is preferably 3 from the viewpoint that raw materials are easily available. R 2 is selected from a hydrogen atom, an alkyl group, and an aryl group, and the alkyl group is preferably a methyl group, an ethyl group, and the like, and the aryl group is preferably a phenyl group.
【０００９】一般式(I) で表される構成単位の具体例と
しては、Specific examples of the structural unit represented by the general formula (I) include:
【化４】 などが挙げられる。Embedded image And the like.
【００１０】本発明に用いるプラスチック成形品は、他
の構成単位として( メタ) アクリロイル基、スチリル
基、アリル基、ビニル基など、共重合可能な二重結合を
有するモノマーに由来する構成単位を有することができ
る。その例を挙げれば、メチル( メタ) アクリレート、
エチル( メタ) アクリレートなどアルキル( メタ) アク
リレート類に由来する構成単位、トリフルオロエチル(
メタ) アクリレート、ヘキサフルオロイソプロピル( メ
タ) アクリレートなどのハロゲン化アルキル( メタ) ア
クリレート類に由来する構成単位、2-ヒドロキシエチル
( メタ) アクリレート、2,3-ジヒドロキシプロピル( メ
タ) アクリレートなどの水酸基を有するヒドロキシアル
キル( メタ) アクリレート類に由来する構成単位、N,N-
ジメチルアクリルアミド、N,N-ジエチルアクリルアミド
などのジアルキルアクリルアミド類に由来する構成単
位、スチレン、ビニルピリジンなどの芳香族ビニルモノ
マーに由来する構成単位、更にはN-ビニルピロリドンな
どのヘテロ環ビニルモノマーに由来する構成単位などで
ある。The plastic molded article used in the present invention has, as other structural units, structural units derived from a monomer having a copolymerizable double bond such as a (meth) acryloyl group, a styryl group, an allyl group, and a vinyl group. be able to. Examples include methyl (meth) acrylate,
Structural units derived from alkyl (meth) acrylates such as ethyl (meth) acrylate, trifluoroethyl (
2-hydroxyethyl, a structural unit derived from alkyl (meth) acrylates such as (meth) acrylate and hexafluoroisopropyl (meth) acrylate
Structural units derived from hydroxyalkyl (meth) acrylates having a hydroxyl group, such as (meth) acrylate, 2,3-dihydroxypropyl (meth) acrylate, N, N-
Structural units derived from dialkylacrylamides such as dimethylacrylamide and N, N-diethylacrylamide, structural units derived from aromatic vinyl monomers such as styrene and vinylpyridine, and further derived from heterocyclic vinyl monomers such as N-vinylpyrrolidone And so on.
【００１１】かかるポリマー中の一般式(I) で表わされ
る構成単位の含有量は特に限定されるものではないが、
少なくとも5 重量％含有されていることが好ましく、ま
た、100 重量％であっても良い。5 重量％未満であれ
ば、酸素透過性と機械的特性との優れたバランスを維持
できなくなる傾向がある。Although the content of the structural unit represented by the general formula (I) in such a polymer is not particularly limited,
It is preferably contained at least 5% by weight, and may be 100% by weight. If it is less than 5% by weight, it tends to be impossible to maintain an excellent balance between oxygen permeability and mechanical properties.
【００１２】本発明の一般式（Ｉ）で示されるモノマー
において、分子中にオルガノシロキサン基を二個有して
いる場合は、重合することによって高い酸素性透過性を
有するポリマーを得ることができる。また、本発明にお
いて得られるポリマーは窒素原子上の置換基を自由に設
計できるため、以下に示す通り良好な力学特性および透
明性を有するプラスチック成形品として非常に有用に用
いられる。When the monomer represented by the general formula (I) of the present invention has two organosiloxane groups in the molecule, a polymer having high oxygen permeability can be obtained by polymerization. . Further, since the polymer obtained in the present invention can freely design the substituent on the nitrogen atom, it is very usefully used as a plastic molded article having good mechanical properties and transparency as shown below.
【００１３】本発明のプラスチック成形品は、以下の方
法により製造することができる。一般式(I) で表わされ
る構成単位を含むポリマーを切削加工によって所望の形
状に加工するか、または、一般式(I) で表わされる構成
単位および修飾可能な官能基を有する構成単位を含むポ
リマーを、所望の形状に加工した後に高分子反応によっ
て改質することもできる。軟質のプラスチック成形品の
場合、モールド重合やスピンキャスト重合などの手法も
用いることができる。その他には、本発明のポリマーを
溶融もしくは溶媒などで溶解し、繊維、フィルム等に成
形することもできる。The molded plastic article of the present invention can be produced by the following method. A polymer containing a structural unit represented by the general formula (I) is processed into a desired shape by cutting, or a polymer containing a structural unit represented by the general formula (I) and a structural unit having a modifiable functional group Can be modified by a polymer reaction after being processed into a desired shape. In the case of a soft plastic molded product, techniques such as mold polymerization and spin-cast polymerization can also be used. Alternatively, the polymer of the present invention can be melted or dissolved with a solvent or the like and formed into fibers, films, or the like.
【００１４】また、本発明において、紫外線吸収剤や色
素、着色剤などを添加することも可能である。In the present invention, it is also possible to add an ultraviolet absorber, a coloring matter, a coloring agent and the like.
【００１５】本発明により、高い酸素透過性、良好な水
濡れ性、良好な光学的特性及び力学的特性を併せ持った
プラスチック成形品を提供することができる。これら
は、コンタクトレンズ、プラスチックレンズなどのレン
ズ材料、ディスプレイ材料等の光学物品として好適に用
いられる。According to the present invention, a plastic molded product having high oxygen permeability, good water wettability, good optical properties and mechanical properties can be provided. These are suitably used as lens articles such as contact lenses and plastic lenses, and optical articles such as display materials.
【００１６】[0016]
【実施例】以下実施例を挙げて本発明を説明するが、本
発明はこれらの例によって限定されるものではない。EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited to these examples.
【００１７】合成例1 (反応中間体A の合成) 100 mlのナス型フラスコにエタノールアミン1.31 g(0.0
214 mol)、3-ヨードプロピルトリス( トリメチルシロキ
シ) シラン20.0 g(0.0428 mol)、エタノール30ml を加
えて60℃で48時間撹拌した。エタノールを減圧下で除去
した後、水酸化ナトリウム水溶液を加え、酢酸エチルで
抽出した。酢酸エチルを減圧下で除去した後、減圧蒸留
を行い、反応中間体A を得た。この反応生成物のプロト
ン核磁気共鳴スペクトルを測定し分析した結果、式：Synthesis Example 1 (Synthesis of Reaction Intermediate A) 1.31 g of ethanolamine (0.0
214 mol), 20.0 g (0.0428 mol) of 3-iodopropyltris (trimethylsiloxy) silane, and 30 ml of ethanol were added, and the mixture was stirred at 60 ° C for 48 hours. After removing the ethanol under reduced pressure, an aqueous sodium hydroxide solution was added, and the mixture was extracted with ethyl acetate. After removing the ethyl acetate under reduced pressure, distillation under reduced pressure was performed to obtain a reaction intermediate A. The proton nuclear magnetic resonance spectrum of this reaction product was measured and analyzed.
【化５】 で表される化合物( 以下、反応中間体A という) である
ことを確認した。Embedded image (Hereinafter, referred to as reaction intermediate A).
【００１８】合成例2 (モノマーA の合成) 200 mlのナス型フラスコに反応中間体A20.0 g(0.027 mo
l)、トルエン100 mlを加え、0 ℃に冷却した後、メタク
リル酸クロリド3.4 g(0.033 mol)をゆっくりと滴下し
た。さらに室温で4 時間撹拌した後、反応系に水を加え
1 時間撹拌した。トルエン層を収集した後、減圧下でト
ルエンを除去し、減圧蒸留を行いモノマーA を得た。こ
の反応生成物のプロトン核磁気共鳴スペクトルを測定し
分析した結果、式：Synthesis Example 2 (Synthesis of Monomer A) 20.0 g of the reaction intermediate A (0.027 mol
l) and 100 ml of toluene were added, and the mixture was cooled to 0 ° C., and 3.4 g (0.033 mol) of methacrylic chloride was slowly added dropwise. After stirring at room temperature for 4 hours, water was added to the reaction system.
Stir for 1 hour. After collecting the toluene layer, toluene was removed under reduced pressure and distillation under reduced pressure was performed to obtain monomer A. The proton nuclear magnetic resonance spectrum of this reaction product was measured and analyzed.
【化６】 で表される化合物( 以下、モノマーA という) であるこ
とを確認した。Embedded image (Hereinafter, referred to as monomer A).
【００１９】実施例1 モノマーA60 部、2,2,2-トリフルオロエチルメタクリレ
ート40部、エチレングリコールジメタクリレート1 部を
混合し、重合開始剤としてアゾビスイソブチロニトリル
0.3 部を添加した後、直径18 mm 、高さ180 mmの試験管
へ移した。このモノマー混合物をアルゴン雰囲気下で脱
気、密封し、まず４０℃で４８時間重合させ、続いて４
０℃〜１１０℃まで２４時間かけて昇温させた後、１１
０℃において４８時間保持し重合体を得た。得られた重
合体は透明で均質であり、べた付きはみられなかった。Example 1 60 parts of monomer A, 40 parts of 2,2,2-trifluoroethyl methacrylate and 1 part of ethylene glycol dimethacrylate were mixed, and azobisisobutyronitrile was used as a polymerization initiator.
After adding 0.3 parts, the mixture was transferred to a test tube having a diameter of 18 mm and a height of 180 mm. The monomer mixture was degassed and sealed under an argon atmosphere, and was first polymerized at 40 ° C. for 48 hours.
After the temperature was raised from 0 ° C. to 110 ° C. over 24 hours, 11
It was kept at 0 ° C. for 48 hours to obtain a polymer. The obtained polymer was transparent and homogeneous, and no stickiness was observed.
【００２０】実施例２ モノマーＡ６０部、メチルメタクリレート４０部、エチ
レングリコールジメタクリレート１部を混合糸、重合開
始剤としてアゾビスイソブチロニトリル０．３部を添加
下後、実施例１と同様に重合した。得られた重合体は透
明で均質であり、べた付きはみられなかった。Example 2 A mixed yarn comprising 60 parts of monomer A, 40 parts of methyl methacrylate and 1 part of ethylene glycol dimethacrylate, and 0.3 part of azobisisobutyronitrile as a polymerization initiator were added. Polymerized. The obtained polymer was transparent and homogeneous, and no stickiness was observed.
【００２１】[0021]
【発明の効果】本発明により、高い透明性及び酸素透過
性、良好な力学特性を有するプラスチック成形品を提供
することができる。According to the present invention, it is possible to provide a plastic molded article having high transparency and oxygen permeability and good mechanical properties.
Claims (9)
を重合して得られることを特徴とするプラスチック成形
品。 【化１】 （Ｒ1 は水素原子またはメチル基であり、Ｒ2 は水素原
子、アルキル基、又はアリール基を示す。ｎは１〜１０
の整数、ｍは１〜６、ａ，ｂ、ｃはそれぞれが互いに０
〜２０の整数、ｄは０〜２００の整数、ｅは１または２
の整数である。Ａ，Ｂはそれぞれ互いに独立に、Ｃ１〜
Ｃ５のアルキル基、フェニル基、およびフルオロアルキ
ル基から選ばれる。）1. A plastic molded article obtained by polymerizing an amine compound represented by the following general formula (I). Embedded image (R 1 is a hydrogen atom or a methyl group, and R 2 is a hydrogen atom, an alkyl group, or an aryl group. N is 1 to 10
M is 1 to 6, and a, b and c are each 0
An integer of 0 to 20, d is an integer of 0 to 200, e is 1 or 2
Is an integer. A and B are each independently C1-
It is selected from a C5 alkyl group, a phenyl group, and a fluoroalkyl group. )
求項１記載のプラスチック成形品。2. The plastic molded article according to claim 1, wherein R 1 is a methyl group.
項１または２記載のプラスチック成形品。3. The plastic molded article according to claim 1, wherein A is a methyl group.
３のいずれかに記載のプラスチック成形品。4. The method according to claim 1, wherein m is 3.
4. The plastic molded article according to any one of the above items 3.
のプラスチック成形品5. The plastic molded article according to claim 1, wherein d = 0.
記載のプラスチック成形品6. The plastic molded product according to claim 1, wherein a = b = c = 1.
共重合成分を有することを特徴とする請求項１〜６のい
ずれかに記載のプラスチック成形品。7. A compound represented by the general formula (I):
The plastic molded article according to any one of claims 1 to 6, further comprising a copolymer component.
スチリル基、アリル基およびビニル基から選ばれる少な
くとも１つを有するモノマーに由来する単位であること
を特徴とする請求項１〜７のいずれかに記載のプラスチ
ック成形品。8. A copolymer component comprising a (meth) acryloyl group,
The plastic molded product according to any one of claims 1 to 7, wherein the unit is a unit derived from a monomer having at least one selected from a styryl group, an allyl group, and a vinyl group.
あることを特徴とする請求項１〜８のいずれかに記載の
プラスチック成形品。9. The plastic molded article according to claim 1, wherein the plastic molded article is a contact lens.
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32667496A JP4061664B2 (en) | 1996-12-06 | 1996-12-06 | Plastic molded product |
| SG1997004332A SG63782A1 (en) | 1996-12-06 | 1997-12-05 | Plastic articles for medical use |
| CA002223905A CA2223905C (en) | 1996-12-06 | 1997-12-05 | Plastic articles for medical use |
| TW086118334A TW369617B (en) | 1996-12-06 | 1997-12-05 | Plastic articles for medical use |
| CN97114356A CN1192961A (en) | 1996-12-06 | 1997-12-05 | Medical plastic article |
| US08/985,722 US5994488A (en) | 1996-12-06 | 1997-12-05 | Plastic articles for medical use |
| KR1019970066490A KR100528421B1 (en) | 1996-12-06 | 1997-12-06 | A novel polymer and plastic articles for ophthalmic lenses comprising The Same |
| EP97309882A EP0862068B1 (en) | 1996-12-06 | 1997-12-08 | Plastic articles for medical use |
| AT97309882T ATE297023T1 (en) | 1996-12-06 | 1997-12-08 | PLASTIC ITEMS FOR MEDICAL APPLICATIONS |
| DE69733406T DE69733406T2 (en) | 1996-12-06 | 1997-12-08 | Plastic articles for medical applications |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32667496A JP4061664B2 (en) | 1996-12-06 | 1996-12-06 | Plastic molded product |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH10170874A true JPH10170874A (en) | 1998-06-26 |
| JP4061664B2 JP4061664B2 (en) | 2008-03-19 |
Family
ID=18190401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP32667496A Expired - Lifetime JP4061664B2 (en) | 1996-12-06 | 1996-12-06 | Plastic molded product |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4061664B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999056167A1 (en) * | 1998-04-28 | 1999-11-04 | Toray Industries, Inc. | Process for producing ocular lens |
| JP2013540188A (en) * | 2010-10-06 | 2013-10-31 | ノバルティス アーゲー | Chain-extending polysiloxane crosslinker with dangling hydrophilic polymer chain |
| US20160108066A1 (en) * | 2014-10-17 | 2016-04-21 | Shin-Etsu Chemical Co., Ltd. | Silicone compound having a radical-polymerizable group and a method for the preparation thereof |
| JP2022516126A (en) * | 2018-12-31 | 2022-02-24 | ダウ シリコーンズ コーポレーション | Branched organosilicon compounds, their preparation methods, and copolymers formed using them. |
-
1996
- 1996-12-06 JP JP32667496A patent/JP4061664B2/en not_active Expired - Lifetime
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999056167A1 (en) * | 1998-04-28 | 1999-11-04 | Toray Industries, Inc. | Process for producing ocular lens |
| JP2013540188A (en) * | 2010-10-06 | 2013-10-31 | ノバルティス アーゲー | Chain-extending polysiloxane crosslinker with dangling hydrophilic polymer chain |
| US20160108066A1 (en) * | 2014-10-17 | 2016-04-21 | Shin-Etsu Chemical Co., Ltd. | Silicone compound having a radical-polymerizable group and a method for the preparation thereof |
| CN105524102A (en) * | 2014-10-17 | 2016-04-27 | 信越化学工业株式会社 | Silicone compound having a radical-polymerizable group and a method for the preparation thereof |
| JP2016079298A (en) * | 2014-10-17 | 2016-05-16 | 信越化学工業株式会社 | Radical polymerizable group-containing silicone compound and production method of the same |
| US9487543B2 (en) * | 2014-10-17 | 2016-11-08 | Shin-Etsu Chemical Co., Ltd. | Silicone compound having a radical-polymerizable group and a method for the preparation thereof |
| JP2022516126A (en) * | 2018-12-31 | 2022-02-24 | ダウ シリコーンズ コーポレーション | Branched organosilicon compounds, their preparation methods, and copolymers formed using them. |
Also Published As
| Publication number | Publication date |
|---|---|
| JP4061664B2 (en) | 2008-03-19 |
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