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WO2013098966A1 - Monomère de silicone et son procédé de production - Google Patents

Monomère de silicone et son procédé de production Download PDF

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Publication number
WO2013098966A1
WO2013098966A1 PCT/JP2011/080311 JP2011080311W WO2013098966A1 WO 2013098966 A1 WO2013098966 A1 WO 2013098966A1 JP 2011080311 W JP2011080311 W JP 2011080311W WO 2013098966 A1 WO2013098966 A1 WO 2013098966A1
Authority
WO
WIPO (PCT)
Prior art keywords
monomer
formula
silicone
ppm
meth
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.)
Ceased
Application number
PCT/JP2011/080311
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English (en)
Japanese (ja)
Inventor
陽介 松岡
規郎 岩切
伸行 吉岡
伸行 坂元
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
NOF Corp
Original Assignee
NOF Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by NOF Corp filed Critical NOF Corp
Priority to PCT/JP2011/080311 priority Critical patent/WO2013098966A1/fr
Publication of WO2013098966A1 publication Critical patent/WO2013098966A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
    • C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
    • C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • G02B1/043—Contact lenses

Definitions

  • the present invention relates to a polymerizable silicone monomer that can be used in the production of ophthalmic devices such as contact lenses, intraocular lenses, and artificial corneas, a method for producing the same, a monomer composition using the silicone monomer, and a weight thereof. Regarding coalescence.
  • Various articles including a biological device are formed from, for example, an organic silicon compound-containing material.
  • One organosilicon compound material useful for biomedical devices such as soft contact lenses is a silicon-containing hydrogel material.
  • silicon-based materials have higher oxygen permeability than water, and therefore, articles having higher oxygen permeability can be provided.
  • Organosilicon compound materials conventionally used for hard contact lenses are highly oxygen permeable, but are harder than materials used for soft contact lenses. Also, since such organosilicon compound materials are hydrophobic, manufacturing lenses using them requires additional processing to provide a hydrophilic surface.
  • TRIS tris (trimethylsiloxy) silyl] propyl methacrylate
  • TRIS is also a hydrophobic monomer, when used as an ophthalmic lens material, for example, it may be copolymerized with a hydrophilic monomer.
  • TRIS has poor compatibility with hydrophilic monomers such as HEMA (2-hydroxyethyl methacrylate).
  • HEMA 2-hydroxyethyl methacrylate
  • transparent polymers cannot be obtained and used as lens materials.
  • many combinations with other hydrophilic monomers such as N-vinylpyrrolidone and N, N-dimethylacrylamide have a strong water repellency when containing water, so TRIS is difficult to use as a material for soft contact lenses. Are known.
  • Patent Documents 2 and 3 propose SiGMA (methyldi (trimethylsiloxy) silylpropylglycerol methacrylate), which is used as a compatibilizer monomer in silicone hydrogel contact lens applications. Since SiGMA has an appropriate oxygen permeation performance, it also plays a role as an oxygen permeation preparation. Since this SiGMA has a hydroxyl group, it is known to express good hydrophilicity.
  • SiGMA methyldi (trimethylsiloxy) silylpropylglycerol methacrylate
  • a silicone monomer represented by the formula (1) is provided.
  • R represents a hydrogen atom or a methyl group.
  • X represents a group selected from the formulas (2a) to (2f).
  • N represents 0 or 1)
  • the silicone monomer represented by the above formula (1) comprising the step of reacting an N- (meth) acryloylamino acid obtained by reacting an amino acid and (meth) acrylic acid with an alkyl halide-modified silicone.
  • a manufacturing method is provided.
  • the silicone monomer is selected from the group consisting of 20 to 60% by mass and 2-hydroxyethyl (meth) acrylate, N-vinylpyrrolidone, N, N-dimethylacrylamide or a mixture of two or more thereof.
  • a monomer composition comprising 40-80% by weight of hydrophilic monomer is provided.
  • a polymer obtained by polymerizing the monomer composition is provided.
  • the silicone monomer of the present invention has a high silicone content, and since it has an amide group or an ester group derived from a hydrophilic amino acid in the molecule, it is highly hydrophilic, and other polymerizable monomers such as (meth) acrylic monomers Because of its high compatibility, when used for the purpose of copolymerization, it is considered that both transparency and oxygen permeability are satisfied at the same time, and it is useful as a silicone monomer used as a raw material for ophthalmic devices. In addition, since the monomer composition and polymer of the present invention utilize the silicone monomer of the present invention, they are useful for the production of ophthalmic devices such as contact lenses that satisfy both transparency and oxygen permeability.
  • X represents a group selected from the above formulas (2a) to (2f).
  • the ratio of the siloxanyl group in one molecule is as large as possible.
  • X is a compound represented by the formula (2a)
  • X is a formula (2c )
  • a compound wherein X is formula (2d) is particularly preferred.
  • X is the formula (2a)
  • R is a methyl group
  • the above reaction is preferably performed in the presence of a base in order to increase the reaction rate.
  • Preferred bases include, for example, inorganic bases such as potassium carbonate, sodium carbonate, sodium hydroxide, potassium hydroxide, and organic bases such as triethylamine and 1,8-diazabicyclo [5,4,0] undec-7-ene (DBU).
  • a base More preferably, potassium carbonate and triethylamine are mentioned.
  • the amount of the base used is about 1 mol to 3 mol with respect to 1 mol of the silicone compound represented by the formula (6).
  • a polymerization inhibitor so that the (meth) acrylic group is not polymerized.
  • the polymerization inhibitor include hydroquinone monomethyl ether, 1,4-dihydroxybenzene, dibutylhydroxytoluene and the like.
  • the inhibitor is preferably added to the reaction solution in an amount of 100 ppm to 10,000 ppm.
  • other monomers can be appropriately contained as required within a range not impairing the above-described properties of the silicone monomer of the present invention.
  • examples of other monomers include 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, glycerol (meth) acrylate, (meth) acrylamide, polyethylene glycol (meth) acrylate, and polypropylene glycol (meth) acrylate.
  • the content ratio in the case of using the other monomer can be appropriately determined within the range not impairing the desired effect of the present invention, but the total amount is usually 40% by mass based on the total amount of the monomer composition. Hereinafter, it is preferably 30% by mass or less.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Cette invention concerne : un monomère de silicone ayant une teneur élevée de silicone, pouvant avoir une transparence et un taux de transmission d'oxygène élevés quand il est copolymérisé avec des monomères polymérisables tels qu'un monomère (méth)acrylique, et se prêtant à une application à l'œil ; un procédé pour le produire ; et une composition monomère et un polymère l'utilisant. Le monomère de silicone selon l'invention est représenté par la formule (1) (R : H ou CH3, X : groupe choisi parmi les formules (2a)-(2f), et n : 0 ou 1). Le monomère est utile pour fabriquer des dispositifs oculaires tels que des lentilles de contact. (1) (2a) (2b) (2c) (2d) (2e) (2f)
PCT/JP2011/080311 2011-12-27 2011-12-27 Monomère de silicone et son procédé de production Ceased WO2013098966A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/JP2011/080311 WO2013098966A1 (fr) 2011-12-27 2011-12-27 Monomère de silicone et son procédé de production

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/JP2011/080311 WO2013098966A1 (fr) 2011-12-27 2011-12-27 Monomère de silicone et son procédé de production

Publications (1)

Publication Number Publication Date
WO2013098966A1 true WO2013098966A1 (fr) 2013-07-04

Family

ID=48696531

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2011/080311 Ceased WO2013098966A1 (fr) 2011-12-27 2011-12-27 Monomère de silicone et son procédé de production

Country Status (1)

Country Link
WO (1) WO2013098966A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014093751A3 (fr) * 2012-12-14 2014-08-28 Novartis Ag Monomères vinyliques contenant un siloxane amphiphile et leurs utilisations

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000191730A (ja) * 1998-12-24 2000-07-11 Toray Ind Inc 眼用レンズ用モノマー、眼用レンズ用ポリマーおよびそれを用いたコンタクトレンズ
JP2000212223A (ja) * 1999-01-21 2000-08-02 Toray Ind Inc モノマ―およびそれを用いたポリマ―、プラスチック成形体
JP2001323024A (ja) * 2000-05-12 2001-11-20 Toray Ind Inc モノマー、ポリマーおよびそれを用いた眼用レンズ
JP2002088119A (ja) * 2000-09-14 2002-03-27 Toray Ind Inc モノマー、ポリマー、眼用レンズおよびコンタクトレンズ
JP2007526364A (ja) * 2004-02-11 2007-09-13 ジョンソン・アンド・ジョンソン・ビジョン・ケア・インコーポレイテッド ヒドロキシおよびシリコーン官能基含有（メタ）アクリルアミドモノマー、ならびに、それらから製造されるポリマー
JP2011528816A (ja) * 2008-07-21 2011-11-24 ノバルティス アーゲー 加水分解性基を有するシリコーン含有ポリマー材料
JP2012017285A (ja) * 2010-07-07 2012-01-26 Nof Corp シリコーンモノマー、その製造方法、単量体組成物及び重合体

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000191730A (ja) * 1998-12-24 2000-07-11 Toray Ind Inc 眼用レンズ用モノマー、眼用レンズ用ポリマーおよびそれを用いたコンタクトレンズ
JP2000212223A (ja) * 1999-01-21 2000-08-02 Toray Ind Inc モノマ―およびそれを用いたポリマ―、プラスチック成形体
JP2001323024A (ja) * 2000-05-12 2001-11-20 Toray Ind Inc モノマー、ポリマーおよびそれを用いた眼用レンズ
JP2002088119A (ja) * 2000-09-14 2002-03-27 Toray Ind Inc モノマー、ポリマー、眼用レンズおよびコンタクトレンズ
JP2007526364A (ja) * 2004-02-11 2007-09-13 ジョンソン・アンド・ジョンソン・ビジョン・ケア・インコーポレイテッド ヒドロキシおよびシリコーン官能基含有（メタ）アクリルアミドモノマー、ならびに、それらから製造されるポリマー
JP2011528816A (ja) * 2008-07-21 2011-11-24 ノバルティス アーゲー 加水分解性基を有するシリコーン含有ポリマー材料
JP2012017285A (ja) * 2010-07-07 2012-01-26 Nof Corp シリコーンモノマー、その製造方法、単量体組成物及び重合体

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014093751A3 (fr) * 2012-12-14 2014-08-28 Novartis Ag Monomères vinyliques contenant un siloxane amphiphile et leurs utilisations
US9103965B2 (en) 2012-12-14 2015-08-11 Novartis Ag Amphiphilic siloxane-containing vinylic monomers and uses thereof
US9541676B2 (en) 2012-12-14 2017-01-10 Novartis Ag Amphiphilic siloxane-containing vinylic monomers and uses thereof

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