WO2020174570A1 - Matériau polymère - Google Patents

Matériau polymère Download PDF

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Publication number
WO2020174570A1
WO2020174570A1 PCT/JP2019/007260 JP2019007260W WO2020174570A1 WO 2020174570 A1 WO2020174570 A1 WO 2020174570A1 JP 2019007260 W JP2019007260 W JP 2019007260W WO 2020174570 A1 WO2020174570 A1 WO 2020174570A1
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group
meth
monomer
polymer material
silicone
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PCT/JP2019/007260
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English (en)
Japanese (ja)
Inventor
康介 佐竹
浅井　健吾
一潤 砂原
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株式会社メニコン
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Priority to JP2020564947A priority Critical patent/JP6974633B2/ja
Priority to PCT/JP2019/007260 priority patent/WO2020174570A1/fr
Publication of WO2020174570A1 publication Critical patent/WO2020174570A1/fr

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    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts
    • G02C7/02—Lenses; Lens systems ; Methods of designing lenses
    • G02C7/04—Contact lenses for the eyes

Definitions

  • the present invention relates to a polymer material, and more specifically to a polymer material suitable for ophthalmic lens applications.
  • Contact lenses are roughly classified into hard contact lenses and soft contact lenses.
  • hard contact lenses have high oxygen permeability because they are formed of a silicone-containing polymer having a siloxane structure (Si-O-Si), but due to their hardness, they are foreign substances during wearing. It may cause a feeling.
  • Soft contact lenses are made from hydrous hydrogel obtained by copolymerizing a hydrophilic monomer, a (meth)acrylic monomer and a cross-linking agent, so that an excellent wearing feeling can be obtained, while a soft contact lens can be used as a hard contact lens. Compared with this, oxygen permeability tends to be low.
  • a silicone hydrogel containing a silicone-based monomer as a further copolymerization component, a soft contact lens having both high oxygen permeability and excellent wearing feeling has been developed.
  • lipids tend to adhere to the surface of soft contact lenses made of silicone hydrogel. Therefore, adhesion of lipids has been suppressed by plasma treatment or mixing a hydrophilic polymer as an internal wetting agent in the hydrogel.
  • methyldi(trimethylsiloxy)silylpropyl is usually used.
  • a silicone-containing monomer having a hydroxyl group such as glycerol methacrylate (also referred to as “SiGMA”) is used (for example, Patent Document 1). This makes it possible to obtain a polymer material that suppresses the adhesion of lipids and is excellent in transparency, but further improvement in antifouling property against lipids is required.
  • the main object of the present invention is to provide a silicone-containing polymer material that contains an internal wetting agent and has excellent transparency, and that has improved antifouling properties against lipids.
  • a polymer material obtained by polymerizing a polymerizable mixture containing (a) a monomer component and (b) a hydrophilic polymer component, wherein (a) the monomer component is: (A-1) A silicone-containing monomer having an anionic group is contained, and the blending amount of the (b) hydrophilic polymer component in the polymerizable mixture is a total blend of the (a) monomer component and the (b) hydrophilic polymer component.
  • a polymeric material is provided that is about 1 part to about 30 parts by weight per 100 parts by weight.
  • the monomer component (a) further comprises (a-2) a hydrophilic monomer.
  • the monomer component (a) further contains (a-3) a silicone-containing monomer having no anionic group.
  • the (a-1) silicone-containing monomer having an anionic group has two or more polymerizable functional groups.
  • the silicone-containing monomer having an anionic group (a-1) has three or more polymerizable functional groups.
  • the silicone-containing monomer (a-1) having an anionic group has a structure represented by the following formula (I).
  • R a1 to R a8 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 50 carbon atoms which may have a hetero atom
  • Z 1 and Z 2 are each independently a group represented by the following formula (1), -R b1 -X-R b2 (1)
  • R b1 is an alkylene group having 1 to 20 carbon atoms which may have a hetero atom
  • R b2 is a (meth)acryloyl group, a vinyl group or an allyl group
  • X is a single bond, —O— or —NR b3 —
  • R b3 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms
  • a 1 is k4 one alkylene group of carbon number of 1 to 12 substituted hydrogen atoms by a group of B 1 (provided that may have a hetero atom other than groups B 1)
  • a 2 is a k5 one alkylene group of carbon number of 1
  • the anionic group comprises a carboxyl group.
  • the weight average molecular weight of the hydrophilic polymer component (b) is 100,000 or more.
  • the hydrophilic polymer component (b) is polyvinylamide.
  • the hydrophilic polymer component (b) comprises at least one selected from poly-N-vinylpyrrolidone, polyalkylene glycols, polysaccharides, poly(meth)acrylic acid and polyvinyl alcohol.
  • the hydrophilic polymer component (b) is poly-N-vinylpyrrolidone.
  • the oxygen permeability coefficient of the polymeric material is 30 Barrer to 120 Barrer. According to another aspect of the present invention, there is provided an ophthalmic medical device including the polymer material. In one embodiment, the ophthalmic medical device is a contact lens.
  • the material can be obtained.
  • the polymer material in one embodiment of the present invention is obtained by polymerizing a polymerizable mixture containing (a) a monomer component and (b) a hydrophilic polymer component. More specifically, the monomer component (a) is polymerized in a state where the monomer component (a) and the hydrophilic polymer component (b) are mixed, preferably in a compatible state.
  • the (b) hydrophilic polymer component used in the present invention is typically a non-polymerizable component having no polymerizable functional group, and the (a) monomer component is polymerized in such a state.
  • a polymer material in which (a) a polymer containing a structural unit derived from a monomer component and (b) a hydrophilic polymer component are highly complexed can be obtained.
  • the “monomer” means a polymerizable compound having one or more polymerizable functional groups. Therefore, a polymerizable compound (also referred to as an oligomer) composed of two or more monomer units and a polymerizable compound having a large molecular weight (also referred to as a macromer or a macromonomer) are also included in the monomer.
  • a polymerizable compound also referred to as an oligomer
  • a polymerizable compound having a large molecular weight also referred to as a macromer or a macromonomer
  • polymerizable functional group examples include (meth)acryloyl group, vinyl group, allyl group and the like.
  • (meth) means arbitrary methyl substitution.
  • (meth)acryloyl means methacryloyl and/or acryloyl. The same applies to other descriptions such as “(meth)acrylic”.
  • the polymerizable mixture contains (a) a monomer component and (b) a hydrophilic polymer component, and the (a) monomer component contains (a-1) a silicone-containing monomer having an anionic group. Since the silicone-containing monomer having an anionic group (a-1) has excellent compatibility with the hydrophilic polymer component (b), and can contribute to the improvement of oxygen permeability and the antifouling property against lipids. A polymer material having excellent transparency and oxygen permeability and further suppressing lipid adhesion can be obtained. Further, the polymerizable mixture may further contain (c) an additive, if necessary.
  • the polymerizable mixture is substantially free of hydroxyl-containing silicone-containing monomers such as SiGMA.
  • substantially free of a silicone-containing monomer having a hydroxyl group means that the content of the monomer in the monomer component is 0.1% by mass or less.
  • the monomer component contains (a-1) a silicone-containing monomer having an anionic group, and preferably (a-2) does not have a hydrophilic monomer and/or (a-3) an anionic group. It further comprises a silicone-containing monomer.
  • the monomer component may further contain (a-4) a hydrophobic monomer, (a-5) a crosslinkable monomer, (a-6) a functional monomer, etc., if necessary.
  • the total content of the (a-1) silicone-containing monomer having an anionic group, the (a-2) hydrophilic monomer, and the (a-3) silicone-containing monomer having no anionic group in the monomer component is, for example, 30.
  • the amount can be from 99% by mass to 99% by mass, preferably from 70% by mass to 95% by mass.
  • the silicone-containing monomer having an anionic group (hereinafter sometimes referred to as the first silicone-containing monomer) has a siloxane structure (Si-O-Si). Due to the above, it is possible to impart high oxygen permeability to the polymer material, and due to having an anionic group, it is possible to contribute to the improvement of the compatibility with the hydrophilic polymer component and the antifouling property against lipid.
  • the silicone-containing monomer having an anionic group does not have a hydroxyl group.
  • the first silicone-containing monomer has one or more polymerizable functional groups, and preferably has two or more, for example, three or more, four or more or five or more polymerizable functional groups.
  • the first silicone-containing monomer have two or more polymerizable functional groups, a polymer material having good mechanical properties can be obtained even when a crosslinkable monomer is not used. Further, it is possible to obtain effects such as reduction of unreacted monomer, and easy release of the polymer material (for example, ophthalmic lens) obtained by the polymerization from the mold during mold polymerization.
  • the number of anionic groups contained in the first silicone-containing monomer is 1 or more, preferably 2-10.
  • the number of anionic groups is within the range, the effect of improving the compatibility with the hydrophilic polymer component and the antifouling property against lipids can be obtained.
  • the amount of anionic groups is too large, for example, when the polymer material of the present invention is used as a contact lens, a disinfectant during cleaning may be attached to cause eye damage, and the water content of the contact lens is high. May become too high, and problems such as difficulty in obtaining appropriate oxygen permeability and mechanical properties may occur.
  • anionic group examples include a carboxyl group, a sulfonic acid group, a phosphoric acid group, and a sulfuric acid ester group (—O—SO 3 ⁇ ).
  • the anionic group is preferably a carboxyl group.
  • the first silicone-containing monomer can be, for example, a macromonomer having a weight average molecular weight of 500 or more, preferably 1,000 to 100,000.
  • a macromonomer having a weight average molecular weight of 500 or more, preferably 1,000 to 100,000.
  • the first silicone-containing monomer may have a structure represented by the following general formula (I), for example.
  • R a1 to R a8 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 50 carbon atoms which may have a hetero atom
  • Z 1 and Z 2 are each independently a group represented by the following formula (1), -R b1 -X-R b2 (1)
  • R b1 is an alkylene group having 1 to 20 carbon atoms which may have a hetero atom
  • R b2 is a (meth)acryloyl group, a vinyl group or an allyl group
  • X is a single bond, —O— or —NR b3 —
  • R b3 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms
  • a 1 is k4 one alkylene group of carbon number of 1 to 12 substituted hydrogen atoms by a group of B 1 (provided that may have a group of B 1 (provided
  • the hydrocarbon group having 1 to 50 carbon atoms defined for R a1 to R a8 can be exemplified by an alkyl group, an aryl group or an aralkyl group.
  • the above alkyl group may be linear, may be branched, and may include a cyclic structure.
  • the alkyl group is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, further preferably a methyl group or an ethyl group, and even more preferably a methyl group.
  • the alkyl group can have a heteroatom.
  • the hetero atom may be contained in a monovalent substituent group substituting a hydrogen atom, and may be contained in a divalent substituent group substituting a group (—CH 2 —) containing a main chain or branched chain carbon atom. May be.
  • Examples of the monovalent substituent containing a hetero atom include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, an alkoxy group having 1 to 3 carbon atoms, a carboxyl group and an amino group.
  • a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom
  • an alkoxy group having 1 to 3 carbon atoms a carboxyl group and an amino group.
  • Examples of the divalent substituent containing a hetero atom include —O—, —NR a9 —, —C( ⁇ O)O—, —NR a9 C( ⁇ O)—, and —NR a9 C( ⁇ O)O.
  • the aryl group or aralkyl group is preferably an aryl group having 6 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms. Specific examples include phenyl group, benzyl group, tolyl group, xylyl group and the like.
  • the above aryl group or aralkyl group can have a hetero atom.
  • Heteroatoms are typically included in monovalent substituents replacing hydrogen atoms.
  • the monovalent substituent containing a hetero atom is as described above.
  • the alkylene group having 1 to 12 carbon atoms defined for the above A 1 to A 4 may be linear, may be branched, and may include a cyclic structure.
  • the alkylene group is preferably an alkylene group having 1 to 10 carbon atoms, and more preferably an alkylene group having 2 to 8 carbon atoms.
  • the alkylene groups defined for A 1 to A 4 above can each have a heteroatom other than a monovalent group having an anionic group (a group of B 1 , B 2 , B 3 or B 4 ).
  • the hetero atom may be included in a monovalent substituent that replaces a hydrogen atom of the alkylene group, and is a divalent substituent that replaces a group (—CH 2 —) containing a carbon atom in the main chain or a branched chain. May be included in.
  • the monovalent substituent and the divalent substituent containing a hetero atom are as described above.
  • B 1 to B 4 may be each independently an organic group having 1 to 8 carbon atoms, preferably 1 to 5 carbon atoms, having an anionic group.
  • B 1 and B 2 include a carboxyl group, a carboxymethyl group, a 2-carboxyethyl group, a 3-carboxypropyl group, a 4-carboxybutyl group, a sulfonic acid group, a sulfomethyl group, a 2-sulfoethyl group, and 2,3.
  • Examples thereof include a disulfopropyl group, a 3-sulfopropyl group, a 4-sulfobutyl group, a phosphoric acid group, a phosphomethyl group, a phosphoethyl group, a 3-phosphopropyl group and a 4-phosphobutyl group.
  • the alkylene group having 1 to 20 carbon atoms defined for R b1 may be linear, branched, or may contain a cyclic structure.
  • the alkylene group is preferably an alkylene group having 1 to 18 carbon atoms, more preferably an alkylene group having 1 to 12 carbon atoms, and further preferably an alkylene group having 1 to 8 carbon atoms.
  • the alkylene group defined for R b1 above can have a heteroatom.
  • the hetero atom may be contained in a monovalent substituent group substituting a hydrogen atom, and may be contained in a divalent substituent group substituting a group (—CH 2 —) containing a main chain or branched chain carbon atom. May be.
  • these substituents have hydrogen-bonding protons, they improve the affinity with the hydrophilic polymer component and the compatibility between the hydrophilic polymer component and other monomers while suppressing the number of introduced anionic groups. be able to. Above all, it is preferable to contain a urethane bond (—NHC( ⁇ O)O—).
  • a urethane bond (—NHC( ⁇ O)O—).
  • R b1 is "- R b3 - urethane bond -R b4 -" having the structure of or "-R b3 - urethane bond -R b4 - - urethane bond -R b5".
  • R b3 , R b4 and R b5 are each independently an alkylene group having 1 to 10 carbon atoms which may have a hetero atom (preferably ether oxygen), and preferably carbon. It may be an alkylene group of the number 1-5.
  • R b2 is preferably a (meth)acryloyl group, in which case X is preferably —O—.
  • R d1 , R d2 , R d4 and R d5 are each independently a linear or branched alkylene group having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms
  • R d3 is a group consisting of a linear, branched or cyclic alkylene group having 1 to 6 carbon atoms or a combination thereof
  • R d6 is hydrogen or a methyl group
  • p1 and p2 are each independently an integer of 0 to 15, p3 is 0 or 1
  • the number of carbon atoms contained in the residue excluding the (meth)acryloyloxy group (CH 2 ⁇ CR d6 —COO—) is 20 or less. )
  • R d7 and R d8 each independently represent a linear or branched alkylene group having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms, R d9 is hydrogen or a methyl group, p4 is an integer of 0 to 15, However, the number of carbon atoms contained in the residue excluding the (meth)acryloyloxy group (CH 2 ⁇ CR d9 —COO—) is 20 or less.
  • L 1 and/or L 2 is a linking group
  • specific examples of the linking group include groups represented by the following formulas (4) to (10) and groups consisting of a combination of two or more of these groups. it can.
  • * represents a bond, and any bond may be bonded to A 1 or A 2 .
  • R e1 , R e2 and R e3 are each independently hydrogen or an alkyl group having 1 to 5 carbon atoms.
  • K1 and k1′ are each independently an integer of 10 to 200, preferably an integer of 15 to 150, and more preferably an integer of 20 to 80.
  • K2 and k3 are each independently an integer of 1 to 3, and are preferably selected so as to satisfy the relationship of k2+k3 ⁇ 3, more preferably the relationship of k2+k3 ⁇ 4. In one embodiment, k2 and k3 are both 1, 2 or 3.
  • K4 and k5 are each independently preferably 1 or 2. In one embodiment, k4 and k5 are both 1 or 2. Moreover, k11 and k12 are each independently preferably 0, 1, or 2. The sum of k4, k5, k11 and k12 (k4+k5+k11+k12) is preferably an integer of 2-8, more preferably an integer of 2-6.
  • k7 is preferably an integer of 50 or less, more preferably 30 or less.
  • k7 is an integer of 1 or more
  • - ⁇ CH 2 -CH 2 -(E) k6 ⁇ k7- is preferably an ethylene (or polyethylene) group or an oxyethylene (or polyoxyethylene) group.
  • K8 is preferably an integer of 0 to 3, more preferably 0, 1 or 2, and further preferably 0 or 1.
  • K9 and k10 are independently 0 or 1.
  • R f1 , R f2 , R f3 and R f4 are each independently a group represented by the above formula (2) or (3)
  • L 3 and L 4 are each independently a divalent or trivalent linking group
  • m1, m2, m4 and m5 are each independently an integer of 0 to 5
  • m3 is an integer of 10 to 200
  • m6 and m7 are each independently an integer of 0 to 5
  • L 3 is a divalent linking group
  • R f2 does not exist
  • L 4 is a divalent linking group
  • R f4 is absent.
  • the mixing ratio of the first silicone-containing monomer in the polymerizable mixture is, for example, 1% by mass to 70% by mass, preferably 5% by mass, based on the total amount of the (a) monomer component and the (b) hydrophilic polymer component. % To 60% by mass, more preferably 10% to 40% by mass.
  • the compounding ratio of the first silicone-containing monomer is within the range, a polymer material having high oxygen permeability and transparency and excellent antifouling property against lipids can be obtained.
  • a hydrophilic monomer can be copolymerized with a first silicone-containing monomer or the like to form a highly hydrophilic silicone-containing polymer, and the resulting polymer material can be used as a hydrogel.
  • the hydrophilic monomer for example, a monomer having a solubility in water at 25° C. of 0.03 g/mL or more, preferably 0.07 g/mL or more (however, a monomer containing a silicon atom and a polymerizable functional group). (Excluding those having two or more groups) can be used.
  • hydrophilic monomer examples include a hydroxyl group-containing alkyl (meth)acrylate having an alkyl group having 1 to 4 carbon atoms, (meth)acrylamide, and N-vinyllactam.
  • the hydrophilic monomers may be used alone or in combination of two or more.
  • the alkyl group of the hydroxyl group-containing alkyl (meth)acrylate may be branched if necessary.
  • Specific examples of the hydroxyl group-containing alkyl (meth)acrylate include hydroxyalkyl (meth)acrylates such as hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate and 4-hydroxybutyl (meth)acrylate, and dihydroxypropyl (meth)acrylate. Examples thereof include dihydroxyalkyl (meth)acrylates such as acrylate, dihydroxybutyl (meth)acrylate, and dihydroxypentyl (meth)acrylate.
  • Examples of the (meth)acrylamide include N,N-dialkyl(meth)acrylamides such as N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N,N-dipropyl(meth)acrylamide, Examples thereof include N,N-dialkylaminoalkyl(meth)acrylamides such as N,N-dimethylaminopropyl(meth)acrylamide and N,N-diethylaminopropyl(meth)acrylamide.
  • N-vinyllactam examples include N-vinylpyrrolidone, N-vinylpiperidone, N-vinylcaprolactam and the like.
  • hydrophilic monomer is not limited to the above.
  • Other hydrophilic monomers that can be used include, for example, alkoxypolyalkylene glycol mono(meth)acrylate, polyalkylene glycol mono(meth)acrylate, (meth)acrylic acid, 1-methyl-3-methylene-2-pyrrolidinone, Examples thereof include maleic anhydride, maleic acid, maleic acid derivatives, fumaric acid, fumaric acid derivatives, aminostyrene, hydroxystyrene and 2-methoxyethyl acrylate.
  • a hydroxyl group-containing alkyl (meth)acrylate having an alkyl group having 1 to 4 carbon atoms N,N-dimethyl (meth)acrylamide, N-vinylpyrrolidone, alkoxypolyalkylene glycol mono (meta ) Acrylate may be preferably used.
  • the blending ratio of the hydrophilic monomer in the polymerizable mixture is, for example, 0.1% by mass to 90% by mass, preferably 20% by mass, based on the total amount of the (a) monomer component and the (b) hydrophilic polymer component.
  • the amount can be set to ⁇ 80 mass %, more preferably 30 mass% to 70 mass %.
  • a polymer material having a high water content can be obtained.
  • the silicone-containing monomer having no anionic group (hereinafter sometimes referred to as the second silicone-containing monomer) further improves the oxygen permeability of the polymer material. It can be further improved.
  • any suitable monomer for example, a monomer used for conventional ophthalmic lens applications
  • examples of such a monomer include silicone-containing monomers (excluding those having a hydroxyl group) described in paragraphs 0039 to 0044 of JP-A-2015-503631, JP-A-2014-40598, paragraph 0060.
  • the silicone-containing monomers described in paragraphs ⁇ 0065 can be mentioned.
  • the second silicone-containing monomer may be used alone or in combination of two or more.
  • the second silicone-containing monomer examples include trimethylsiloxydimethylsilylmethyl(meth)acrylate, trimethylsiloxydimethylsilylpropyl(meth)acrylate, methylbis(trimethylsiloxy)silylpropyl(meth)acrylate, tris(trimethylsiloxy)silyl.
  • Propyl(meth)acrylate mono[methylbis(trimethylsiloxy)siloxy]bis(trimethylsiloxy)silylpropyl(meth)acrylate, tris[methylbis(trimethylsiloxy)siloxy]silylpropyl(meth)acrylate, methylbis(trimethylsiloxy)silylpropyl Glyceryl (meth)acrylate, tris(trimethylsiloxy)silylpropyl glyceryl(meth)acrylate, mono[methylbis(trimethylsiloxy)siloxy]bis(trimethylsiloxy)silylpropylglyceryl(meth)acrylate, trimethylsilylethyltetramethyldisiloxypropylglyceryl( (Meth)acrylate, trimethylsilylmethyl(meth)acrylate, trimethylsilylpropylglyceryl(meth)acrylate, trimethylsilylpropyl(meth)acrylate, trimethylsiloxydimethyl
  • the second silicone-containing monomer mono(meth)acryloyloxypropyl-terminated mono-n-butyl terminated polydimethylsiloxane, mono(meth)acryloyloxypropyl-terminated mono-n-methyl terminated polydimethylsiloxane, Mono(meth)acryloyloxypropyl-terminated mono-n-butyl-terminated polydiethylsiloxane, mono(meth)acryloyloxypropyl-terminated mono-n-methyl-terminated polydiethylsiloxane, mono(meth)acryloylaminopropyl-terminated mono-n-butyl-terminated Polydimethylsiloxane, mono(meth)acryloylaminopropyl terminated mono-n-methyl terminated polydimethylsiloxane, mono(meth)acryloylaminopropyl terminated mono-n-butyl terminated polydiethylsi
  • the mixing ratio of the second silicone-containing monomer in the polymerizable mixture is, for example, 0% by mass to 70% by mass, preferably 5% by mass, based on the total mixing amount of the (a) monomer component and the (b) hydrophilic polymer component. % To 60% by mass, more preferably 10% to 40% by mass. When the content ratio of the second silicone-containing monomer is within the range, a polymer material having high oxygen permeability while maintaining transparency can be obtained.
  • the total blending ratio of the first silicone-containing monomer and the second silicone-containing monomer in the polymerizable mixture is, for example, from 1% by mass to the total blending amount of the (a) monomer component and (b) hydrophilic polymer component.
  • the amount can be 90% by mass, preferably 10% by mass to 80% by mass, more preferably 20% by mass to 70% by mass. It can be said that one of the features of the present invention is that compatibility with the hydrophilic polymer component can be secured even when the blending ratio of the silicone-containing monomer is high.
  • a hydrophobic monomer is added as necessary for the purpose of improving the copolymerization reactivity, adjusting the hardness or mechanical strength of the polymer material, and the like.
  • the hydrophobic monomer for example, a monomer having a solubility in water at 25° C. of less than 0.03 g/mL (excluding those containing a silicon atom and those having two or more polymerizable functional groups) is used. Can be done.
  • hydrophobic monomer monomers conventionally used for ophthalmic lens materials can be appropriately used.
  • an alkyl(meth)acrylate having a solubility in water at 25° C. of less than 0.03 g/mL for example, an alkyl(meth)acrylate having an alkyl group having 20 or less carbon atoms
  • an alkoxyalkyl(meth) examples thereof include acrylates (eg, alkoxyalkyl (meth)acrylates having an alkoxyalkyl group having 20 or less carbon atoms).
  • the alkyl (meth)acrylate may have a substituent such as a hydroxyl group.
  • the blending ratio of the hydrophobic monomer in the polymerizable mixture is, for example, 0% by mass to 40% by mass, preferably 0% by mass to 30% by mass based on the total amount of the (a) monomer component and the (b) hydrophilic polymer component.
  • the content may be in the range of% by mass, more preferably 0 to 20% by mass. When the content ratio of the hydrophobic monomer is within the range, a polymer material having excellent transparency and mechanical strength can be obtained.
  • crosslinkable monomer is added as needed for the purpose of improving the mechanical strength and shape stability of the polymer material.
  • crosslinkable monomer a monomer having two or more polymerizable functional groups (excluding those containing a silicon atom) is used.
  • crosslinkable monomer examples include butanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, and diethylene glycol di(meth)acrylate.
  • the blending ratio of the crosslinkable monomer in the polymerizable mixture is set appropriately according to the purpose.
  • the monomer described in (a-1) or (a-3) above is polyfunctional, it is not essential to use the crosslinkable monomer, and the mixing ratio can be 0%.
  • a crosslinkable monomer is used, its mixing ratio is, for example, 2% by mass or less, 1% by mass or less, or 0.5% by mass with respect to the total compounding amount of the (a) monomer component and the (b) hydrophilic polymer component. It can be:
  • the functional monomer is added as needed for the purpose of imparting a predetermined function to the polymer material.
  • the functional monomer include a polymerizable dye, a polymerizable ultraviolet absorber and a polymerizable ultraviolet absorber.
  • polymerizable dye examples include, for example, 1-phenylazo-4-(meth)acryloyloxynaphthalene, 1-phenylazo-2-hydroxy-3-(meth)acryloyloxynaphthalene, 1-naphthylazo-2-hydroxy-3.
  • polymerizable ultraviolet absorber examples include, for example, 2-hydroxy-4-(meth)acryloyloxybenzophenone, 2-hydroxy-4-(meth)acryloyloxy-5-t-butylbenzophenone, 2-hydroxy-4. -(Meth)acryloyloxy-2',4'-dichlorobenzophenone, 2-hydroxy-4-(2'-hydroxy-3'-(meth)acryloyloxypropoxy)benzophenone and other benzophenone-based polymerizable ultraviolet absorbers; 2 -(2'-Hydroxy-5'-(meth)acryloyloxyethylphenyl)-2H-benzotriazole, 2-(2'-hydroxy-5'-(meth)acryloyloxyethylphenyl)-5-chloro-2H- Benzotriazole, 2-(2'-hydroxy-5'-(meth)acryloyloxypropylphenyl)-2H-benzotriazole, 2-(2'-hydroxy-(
  • polymerizable ultraviolet absorbing dye examples include, for example, 2,4-dihydroxy-3(p-styrenoazo)benzophenone, 2,4-dihydroxy-5-(p-styrenoazo)benzophenone and 2,4-dihydroxy-3.
  • the total blending amount of the above functional monomers is, for example, 0.001 part by mass to 5 parts by mass, preferably 0.05 part by mass, relative to 100 parts by mass of the total blending amount of the (a) monomer component and (b) hydrophilic polymer component. It can be from 3 parts by mass to 3 parts by mass.
  • hydrophilic Polymer component any suitable polymer capable of imparting surface hydrophilicity to the polymer material can be used.
  • polymers such as polyvinylamide (eg, polyvinyllactam), polyamide, polylactone, polyimide, polylactam, etc. can be used as the hydrophilic polymer.
  • the hydrophilic polymer may be a random copolymer composed of two or more kinds of monomers, an alternating copolymer, a block copolymer, or a graft copolymer.
  • a polymer having a cyclic structure in the main chain or side chain for example, a cyclic amide structure or a cyclic imide structure can be preferably used.
  • the hydrophilic polymer component only one hydrophilic polymer may be used, or two or more hydrophilic polymers may be used in combination.
  • hydrophilic polymer examples include poly-N-vinylpyrrolidone, poly-N-vinyl-2-piperidone, poly-N-vinyl-2-caprolactam, poly-N-vinyl-3-methyl-2-caprolactam, Poly-N-vinyl-3-methyl-2-piperidone, poly-N-vinyl-4-methyl-2-piperidone, poly-N-vinyl-4-methyl-2-caprolactam, poly-N-vinyl-3- Ethyl-2-pyrrolidone and poly-N-vinyl-4,5-dimethyl-2-pyrrolidone, polyvinylimidazole, poly-NN-dimethylacrylamide, polyvinyl alcohol, poly(meth)acrylic acid, poly(2-hydroxyethyl) ) (Meth)acrylates, polyalkylene glycols such as polyethylene glycol, poly-2-ethyl oxazoline, heparin polysaccharides, polysaccharides, and copo
  • poly-N-vinylpyrrolidone polyalkylene glycol, polysaccharides, poly(meth)acrylic acid, polyvinyl alcohol, poly(2-hydroxyethyl)(meth)acrylate and the like can be preferably used.
  • the weight average molecular weight of the hydrophilic polymer is, for example, 100,000 or more, preferably 150,000 to 2,000,000, more preferably 300,000 to 1,800,000, and further preferably 500,000 to 1 , 500,000.
  • the K value of the hydrophilic polymer may be, for example, 30 to 150, preferably 60 to 120, and more preferably 90 to 120.
  • the K value is determined by the Fikentscher formula by measuring the viscosity according to the first method ⁇ 2.53> of the viscosity measurement method in the 16th revised Japanese Pharmacopoeia and according to the method described in the column of “K value” described in the Pharmacopoeia. be able to.
  • the content of the hydrophilic polymer component in the polymerizable mixture is typically 1 part by mass to 30 parts by mass, based on 100 parts by mass of the total amount of the (a) monomer component and the (b) hydrophilic polymer component.
  • the amount can be preferably 3 parts by mass to 20 parts by mass, more preferably 5 parts by mass to 15 parts by mass.
  • the blending amount of the hydrophilic polymer is within the range, a polymer material having excellent surface hydrophilicity can be obtained.
  • additive Any appropriate additive can be selected as the additive depending on the purpose.
  • the additive include a polymerization initiator and an organic solvent.
  • the polymerization initiator is appropriately selected according to the polymerization method.
  • the thermal polymerization initiator used for the polymerization by heating include 2,2′-azobisisobutyronitrile, 2,2′-azobis(2,4-dimethylvaleronitrile), benzoyl peroxide, t-butylhydro. Examples thereof include peroxide, cumene hydroperoxide, lauroyl peroxide, t-butylperoxyhexanoate, and 3,5,5-trimethylhexanoyl peroxide.
  • These thermal polymerization initiators can be used alone or in combination of two or more.
  • the blending amount of the thermal polymerization initiator in the polymerizable mixture is preferably 0.001 to 2 parts by mass based on 100 parts by mass of the total blending amount of the (a) monomer component and the (b) hydrophilic polymer component. It is more preferably 0.01 part by mass to 1 part by mass.
  • Examples of the photopolymerization initiator used in the polymerization by irradiation with light include phosphines such as 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (TPO) and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide.
  • phosphines such as 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (TPO) and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide.
  • Oxide-based photopolymerization initiators such as methyl orthobenzoylbenzoate, methylbenzoyl formate, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzoin-n-butyl ether; 2-hydroxy -2-Methyl-1-phenylpropan-1-one (HMPPO), p-isopropyl- ⁇ -hydroxyisobutylphenone, pt-butyltrichloroacetophenone, 2,2-dimethoxy-2-phenylacetophenone, ⁇ , ⁇ - Phenone-based photopolymerization initiators such as dichloro-4-phenoxyacetophenone and N,N-tetraethyl-4,4-diaminobenzophenone; 1-hydroxycyclohexyl phenyl ketone; 1-phenyl-1,2-propan
  • the blending amount of the photopolymerization initiator and the photosensitizer in the polymerizable mixture is preferably 0.001 part by mass based on 100 parts by mass of the total blending amount of the (a) monomer component and the (b) hydrophilic polymer component. To 2 parts by mass, more preferably 0.01 part to 1 part by mass.
  • the water-soluble organic solvent is preferable as the organic solvent.
  • the water-soluble organic solvent alcohol having 1 to 4 carbon atoms, acetone, methyl ethyl ketone, dimethylformamide, dimethyl sulfoxide, acetonitrile, N-methyl-2-pyrrolidone, dimethoxyethane, tetrohydrofuran, etc. can be used.
  • the compatibility between the monomer components or between the hydrophilic polymer component and the monomer component can be improved. Further, the water-soluble organic solvent can be easily removed by immersion in water.
  • the blending amount of the organic solvent in the polymerizable mixture is, for example, 40 parts by mass or less, preferably 25 parts by mass or less, and more preferably 10 parts by mass with respect to 100 parts by mass in total of the monomer component and the hydrophilic polymer component in the polymerizable mixture. It may be part by weight, more preferably 0 to 5 parts by weight. In the present invention, since the compatibility of each component in the polymerizable mixture is good, the blending amount of the water-soluble organic solvent can be reduced.
  • additives other than the above additives conventionally used for ophthalmic lens applications can be used.
  • a cooling agent, a thickening agent, a surfactant and a non-polymerizable pigment, an ultraviolet absorbent or an ultraviolet absorbent pigment, etc. may be mentioned.
  • the blending amount of the above-mentioned other additives in the polymerizable mixture is, for example, 0.01 to 5 parts by mass, preferably 100 parts by mass based on 100 parts by mass of the total blending amount of the (a) monomer component and the (b) hydrophilic polymer. Can be 0.01 to 3 parts by mass.
  • a polymerizable mixture containing the above components is heated and/or irradiated with light (ultraviolet and/or visible light) to copolymerize each monomer component in the polymerizable mixture.
  • light ultraviolet and/or visible light
  • the bulk polymerization method or the solution polymerization method can be used as the polymerization method.
  • some of the monomer components may remain unpolymerized.
  • a solvent that does not participate in the reaction may remain in the obtained polymer.
  • the obtained polymer material is dipped in water or an organic solvent or a mixed solution thereof, and preferably by repeating this, Treatment may be applied to elute the residue and remove it from the polymeric material.
  • the above polymerizable mixture can be reacted by a casting method.
  • the polymerizable mixture is heated and polymerized by the mold method, the polymerizable mixture is filled in a mold corresponding to the desired shape of the ophthalmic lens material, and the mold is gradually heated.
  • the heating temperature and heating time for heating the polymerizable mixture in the mold are appropriately set according to the composition of the polymerizable mixture and the like.
  • the heating temperature is preferably 50°C or higher and 150°C or lower, more preferably 60°C or higher and 140°C or lower.
  • the heating time for heating the polymerizable mixture in the mold is preferably 10 minutes or more and 120 minutes or less, more preferably 20 minutes or more and 60 minutes or less.
  • the mold when the polymerizable mixture is polymerized by light irradiation, after filling the polymerizable mixture into the mold corresponding to the shape of the desired ophthalmic lens material, the mold is irradiated with light.
  • the material of the mold used for polymerization by light irradiation is not particularly limited as long as it is a material that can transmit light necessary for polymerization.
  • the wavelength of light with which the polymerizable mixture in the mold is irradiated is appropriately set according to the type of photopolymerization initiator used and the like.
  • the light illuminance and the irradiation time are appropriately set depending on the composition of the polymerizable mixture and the like.
  • the light illuminance is preferably 0.1 mW/cm 2 to 100 mW/cm 2 or less.
  • the irradiation time is preferably 1 minute or more. Light with different illuminance may be applied stepwise.
  • the -A polymer material having a desired shape can be obtained by the polymerization in the template method.
  • the polymer material as the obtained molded body may be subjected to mechanical processing such as cutting and polishing, if necessary.
  • the cutting may be performed over the entire surface of one or both surfaces of the polymer material, or may be performed over a part of one or both surfaces of the polymer material.
  • the polymer material of the present invention contains a hydrophilic polymer component as an internal wetting agent, it has excellent surface hydrophilicity, but for the purpose of further surface modification, low temperature plasma treatment, atmospheric pressure plasma, corona discharge, etc. A modification treatment can be performed.
  • the oxygen permeability coefficient (Dk value) of the polymer material in one embodiment of the present invention is preferably 30 Barrer to 120 Barrer, more preferably 40 Barrer to 110 Barrer, and further preferably 50 Barrer to 100 Barrer.
  • the water content of the polymer material in one embodiment of the present invention is preferably 10% by mass or more, more preferably 30% by mass or more, and further preferably 35% by mass to 70% by mass.
  • the Young's modulus of the polymer material in one embodiment of the present invention is preferably 0.05 MPa to 1.5 MPa, more preferably 0.1 MPa to 0.8 MPa, still more preferably 0.15 MPa to 0.7 MPa.
  • urethane dimethacrylate having a secondary amine was synthesized by the above synthetic route.
  • the specific synthetic procedure is as follows. 1) Diethanolamine (21.04 g, 200.0 mmol) and dichloromethane (200.38 g) were added to a 1 L brown eggplant flask, and the mixture was stirred at 0° C. in an ice bath. Di-tert-butyl dicarbonate (48.02 g, 220.0 mmol) was dissolved in dichloromethane (49.81 g) using a 100 mL dropping funnel, and the mixture was added dropwise over 30 minutes.
  • the dropping funnel was washed with a small amount of dichloromethane three times and added to the reaction solution. After completion of the dropping, the reaction solution was returned to room temperature and stirred for 1 hour. 2) p-Methoxyphenol (0.042 g, 0.34 mmol) and tetrakis(2,4-pentanedionato)zirconium(IV) (0.402 g, 0.82 mmol) were added to the reaction solution, and the mixture was cooled to 0° C. in an ice bath. It was stirred at.
  • Karenz MOI (68.27 g, 440.0 mmol) was added dropwise with a 100 mL dropping funnel over 40 minutes.
  • the dropping funnel was washed with a small amount of dichloromethane three times and added to the reaction solution. After completion of the dropping, the reaction solution was returned to room temperature and stirred for 1 hour. Then, 20.04 g of distilled water was added, and the mixture was further stirred at room temperature for 1 hour. 3) Trifluoroacetic acid (228.11 g, 2.0 mol) was added to the reaction solution, a Dimroth condenser was attached, and the mixture was stirred at 40° C. for 4 hours in an oil bath. 4) The reaction solution was returned to room temperature and then moved to an ice bath, and triethylamine (202.95 g, 2.1 mol) was slowly added to neutralize.
  • the silicone macromonomer A was synthesized by the synthetic route shown above.
  • the specific synthetic procedure is as follows. 1) In a 500 mL brown eggplant-shaped flask, succinic anhydride-modified silicone at both ends (56.60 g, functional group equivalent of 1590 g/mol to 17.8 mmol of average molecular weight 3180 g/mol), hexane 55.34 g, urethane dimethacrylate having secondary amine (18.48 g, 44.5 mmol) was added, a Dimroth condenser was attached, and the mixture was stirred in an oil bath at 40°C for 2 hours. 2) After returning the reaction solution to room temperature, it was transferred to a 2 L separating funnel.
  • Liquid separation operation was performed by adding 600 mL of hexane and 300 mL of acetonitrile. The lowermost layer separated into three layers was discarded. To the remaining solution, 300 mL of acetonitrile was added, the liquid separation operation was performed again, and the lowermost layer separated into three layers was discarded. 3) 300 mL of acetonitrile was added to the remaining solution, and liquid separation operation was performed again. The upper layer and the middle layer separated into three layers were transferred to a 1 L brown flask, p-methoxyphenol (0.022 g, 0.018 mmol) was added, and the mixture was evaporated under reduced pressure to obtain 56.33 g of a highly viscous liquid. When the molecular weight of the silicone macromonomer A obtained by the SEC measurement was determined, the number average molecular weight (Mn) was 6000 and the weight average molecular weight (Mw) was 7,000 (in terms of polystyrene).
  • the dropping funnel was washed with a small amount of dichloromethane three times and added to the reaction solution. After the dropping was completed, the reaction solution was returned to room temperature and stirred for 20 hours. 2) Triethylamine (23.00 g, 227.2 mmol) was added to the reaction solution, and the mixture was stirred at 0°C in an ice bath. Methacryloyl chloride (23.20 g, 221.9 mmol) was added dropwise with a dropping funnel over 20 minutes. The dropping funnel was washed with a small amount of dichloromethane three times and added to the reaction solution. After completion of dropping, the reaction solution was returned to room temperature and stirred for 1.5 hours.
  • the silicone macromonomer B was synthesized by the synthetic route shown above.
  • the specific synthetic procedure is as follows. 1) In a 200 mL brown eggplant flask (44.12 g, 15.0 mmol as an average molecular weight of 2940 g/mol from a functional group equivalent of 1470 g/mol), 45.22 g of hexane, dimethacrylate having a secondary amine (9.10 g, 37.7 mmol). ) was added, a Dimroth condenser was attached, and the mixture was stirred at 40°C in an oil bath for 3 hours. 2) After returning the reaction solution to room temperature, it was transferred to a 2 L separating funnel.
  • Silicone macromonomer C was synthesized by the synthetic route shown above. The specific synthetic procedure is as follows. 1) To a 300 mL eggplant flask, succinic anhydride-modified silicone having both ends (114.45 g, a functional group equivalent of 956 g/mol and an average molecular weight of 1912 g/mol of 59.9 mmol) and ethylene glycol (1.86 g, 30.0 mmol) were added. Triethylamine (18.25 g, 180.3 mmol) was added dropwise at room temperature over 7 minutes. 2) The mixture was stirred in an oil bath at 45°C for 30 minutes.
  • Silicone macromonomer D was synthesized by the synthetic route shown above. The specific synthetic procedure is as follows. 1) In a 100 mL brown eggplant-shaped flask, succinic anhydride-modified silicone having both ends (28.60 g, 15.0 mmol as an average molecular weight of 1906 g/mol from functional group equivalent of 953 g/mol), glycerol dimethacrylate (8.57 g, 37.5 mmol), Triethylamine (4.57 g, 45.1 mmol) was added, and the mixture was stirred at room temperature for 30 minutes, equipped with a Dimroth condenser, and stirred at 40° C.
  • Silicone macromonomer F was synthesized by the above synthetic route. The specific synthetic procedure is as follows. 1) In a 100 mL brown eggplant-shaped flask, succinic anhydride-modified silicone (both ends having a functional group equivalent of 953 g/mol and an average molecular weight of 1906 g/mol, 28.82 g, 15.0 mmol), HOB (5.95 g, 37.6 mmol), and triethylamine were placed in a 100 mL brown eggplant flask.
  • the measurement was performed using a THF solution having a sample concentration of about 0.3 mg/10 mL under the conditions of flow rate: 1.0 mL/min, mobile phase: THF, column temperature: 40°C.
  • a calibration curve was prepared from polystyrene standard solutions having different molecular weights, and the number average molecular weight (Mn), the weight average molecular weight (Mw), and the molecular weight distribution (Mw/Mn) were calculated.
  • Example 1 13 parts by mass of PVP (K-90) (manufactured by BASF) as a hydrophilic polymer component, 10 parts by mass of a silicone macromonomer A as a first silicone-containing monomer, and 20 parts by mass of AA-PDMS as a second silicone-containing monomer. Parts, 31 parts by mass of DMAA (manufactured by KJ Chemical Co., Ltd.) as a hydrophilic monomer, 5 parts by mass of Bremmer PME-200 (manufactured by NOF CORPORATION) and 6 parts by mass of 2-MTA (manufactured by Osaka Organic Chemical Company), hydrophobic.
  • PVP K-90
  • HOB manufactured by Kyoeisha Chemical Co., Ltd.
  • HMEPBT manufactured by Daiwa Kasei Co., Ltd., DAISORB-T31
  • RB246 manufactured by ARRAN Co.
  • 0.01 parts by mass, 1.0 part by mass of TPO (manufactured by Daiwa Kasei, IHI-PI-TPO) as a polymerization initiator, and 4 parts by mass of IPA as a water-soluble organic solvent were mixed to prepare a polymerizable mixture. ..
  • the polymerizable mixture was poured into a mold having a contact lens shape (made of polypropylene, corresponding to a contact lens having a diameter of 14.2 mm and a thickness of 0.08 mm). Then, at room temperature, this template was irradiated with blue LED light having a main wavelength of 405 nm (illuminance at 405 nm: 1.5 mW/cm 2 ) for 20 minutes to perform photopolymerization. After the polymerization, the contact lens-shaped polymer material was taken out from the mold.
  • a contact lens shape made of polypropylene, corresponding to a contact lens having a diameter of 14.2 mm and a thickness of 0.08 mm.
  • Examples 2 to 14 A contact lens-shaped polymer material was obtained in the same manner as in Example 1 except that the polymerizable mixture was prepared by mixing the components so as to have the composition shown in Table 1.
  • a contact lens-shaped polymer material was obtained in the same manner as in Example 1 except that the polymerizable mixture was prepared by mixing the components so as to have the composition shown in Table 1.
  • the polymer materials obtained in the above Examples and Comparative Examples were immersed in a phosphate buffer solution having a pH of 7.5 and swollen until equilibrium, and then autoclave sterilized at 121° C. for 20 minutes to obtain the same amount of the new phosphoric acid. What was equilibrated by substituting the buffer solution was subjected to the following characteristic evaluations. However, in the measurement of the oxygen transmission coefficient, the same as the above except that a PP mold that can obtain a plate-shaped sample having an average thickness of about 0.3 mm was used instead of the mold having a contact lens shape. Polymerization, hydration treatment, and sterilization treatment were performed on the plate, and a plate-shaped sample processed into a circle having a diameter of 14.0 mm was used. The results are shown in Table 1.
  • a Seikaken film oxygen permeability meter manufactured by Rika Seiki Co., Ltd.
  • the oxygen permeability coefficient of the lens was calculated according to the following formula.
  • Dk value R ⁇ (IS/IR) ⁇ (TS/TR) ⁇ (PR/PS)
  • the meanings of the symbols in the above formulas are as follows.
  • R Dk value of reference standard (129) IS: Current value of measurement sample ( ⁇ A) IR: Current value of reference standard ( ⁇ A) TS: Average thickness of measurement sample (mm) TR: Average thickness of reference standard (mm) PS: Atmospheric pressure (mmHg) when measuring the measurement sample PR: Atmospheric pressure (mmHg) during reference standard measurement
  • the polymer material of the example obtained by using the silicone-containing monomer having an anionic group has high transparency and oxygen permeability, and the polymer material of the comparative example has antifouling property against lipid. was better than.
  • the polymer material of the present invention is suitably used for ophthalmic medical devices, for example, ophthalmic lenses such as contact lenses, intraocular lenses, artificial corneas, corneal onlays, and corneal inlays.
  • ophthalmic lenses such as contact lenses, intraocular lenses, artificial corneas, corneal onlays, and corneal inlays.

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Abstract

L'invention concerne un matériau polymère contenant une silicone, qui contient un mouillant interne, présente une excellente transparence et possède des propriétés anti-salissures améliorées contre les lipides. Un matériau polymère selon la présente invention est obtenu par polymérisation d'un mélange polymérisable contenant (a) un constituant monomère et (b) un constituant polymère hydrophile, le constituant polymère (a) contenant un monomère contenant une silicone ayant (a-1) un groupe anionique, la teneur en mélange polymérisable du constituant polymère hydrophile (b) étant approximativement de 1 partie en masse à environ 30 parties en masse pour 100 parties en masse de la totalité du constituant monomère (a) et du constituant polymère hydrophile (b).
PCT/JP2019/007260 2019-02-26 2019-02-26 Matériau polymère WO2020174570A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023106395A1 (fr) * 2021-12-10 2023-06-15 三菱ケミカル株式会社 Composition durcissable, corps moulé, hydrogel de silicone, procédé de production d'hydrogel de silicone et macromonomère

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Publication number Priority date Publication date Assignee Title
JP2005513173A (ja) * 2001-09-10 2005-05-12 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 内部湿潤剤を含有している生体医学装置
JP2014505067A (ja) * 2011-02-01 2014-02-27 ディーエスエム アイピー アセッツ ビー．ブイ． 親水性末端基を持つシリコーン含有モノマー
JP2016540087A (ja) * 2013-12-10 2016-12-22 モメンティブ パフォーマンス マテリアルズ インコーポレイテッド 親水性シリコーン組成物
WO2017103791A1 (fr) * 2015-12-15 2017-06-22 Novartis Ag Polysiloxanes polymérisables avec substituants hydrophiles

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005513173A (ja) * 2001-09-10 2005-05-12 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 内部湿潤剤を含有している生体医学装置
JP2014505067A (ja) * 2011-02-01 2014-02-27 ディーエスエム アイピー アセッツ ビー．ブイ． 親水性末端基を持つシリコーン含有モノマー
JP2016540087A (ja) * 2013-12-10 2016-12-22 モメンティブ パフォーマンス マテリアルズ インコーポレイテッド 親水性シリコーン組成物
WO2017103791A1 (fr) * 2015-12-15 2017-06-22 Novartis Ag Polysiloxanes polymérisables avec substituants hydrophiles

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023106395A1 (fr) * 2021-12-10 2023-06-15 三菱ケミカル株式会社 Composition durcissable, corps moulé, hydrogel de silicone, procédé de production d'hydrogel de silicone et macromonomère

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