Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
  • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
  • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
  • A61L27/14—Macromolecular materials
  • A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• • 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
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/04—Polysiloxanes
  • C08G77/38—Polysiloxanes modified by chemical after-treatment

Definitions

• the present invention relates to polysiloxane compounds, polymers, hydrogels, medical materials, and methods for producing polysiloxane compounds.
• Monomers containing siloxane have been known as compounds used in medical materials, including ophthalmic devices.
• 3-[tris(trimethylsiloxy)silyl]propyl methacrylate (TRIS) is widely used as a monomer for ophthalmic devices.
• TRIS tris(trimethylsiloxy)silyl]propyl methacrylate
• Polymers obtained by copolymerizing this TRIS with hydrophilic monomers N,N-dimethylacrylamide and N-vinyl-2-pyrrolidone have the beneficial characteristic of being highly oxygen permeable.
• highly hydrophobic siloxane monomers are not highly compatible with these hydrophilic monomers, and there is a problem that phase separation occurs when hydrogels that are used as medical materials are produced, resulting in cloudy whiteness.
• Patent Document 1 describes siloxanes having primary or secondary hydroxyl groups represented by the following formulas (a) and (a').
• Patent Document 2 describes a siloxane having primary and secondary hydroxyl groups on the siloxane side chain, as shown in the following formula (b).
• the present invention aims to provide a polysiloxane compound suitable for medical materials, a polymer using the polysiloxane compound, a hydrogel containing the polymer, a medical material containing the polymer, and a method for producing the polysiloxane compound.
• the present invention provides a polysiloxane compound that contains one or more (meth)acryloxy groups in one molecule and has a tertiary hydroxyl group at the end of the side chain of the polysiloxane compound.
• Such polysiloxane compounds are suitable for use in medical materials.
• the polysiloxane compound is preferably represented by the following general formula (1).
• Z's are each independently an organic group having 1 to 20 carbon atoms
• R's are each independently a monovalent hydrocarbon group having 1 to 6 carbon atoms
• R's are each independently a monovalent hydrocarbon group having 3 to 20 carbon atoms and having a tertiary hydroxyl group at an end, which may contain an ether bond
• n is an integer from 0 to 200
• m is an integer from 3 to 200, with the proviso that at least one Z is a (meth)acryloxy group.
• Such polysiloxane compounds are suitable for use in medical materials.
• Z is represented by the following general formula (2).
• X is a hydrogen atom or a methyl group, and the dashed line represents a bond to the silicon atom.
• Such polysiloxane compounds are even more suitable for use in medical materials.
• the R is a methyl group.
• the polysiloxane compounds of the present invention are preferably as described above.
• R' is represented by the following general formula (3) or (4).
• k represents an integer of 0 to 5
• the dashed lines represent bonds to the silicon atom.
• the polysiloxane compounds of the present invention are more preferably as described above.
• k in the general formula (3) is 0 or 1.
• Such polysiloxane compounds are even more suitable for use in medical materials.
• n is an integer from 0 to 100
• m is an integer from 3 to 100
• m/(n+m) is 0.15 or more.
• Such polysiloxane compounds are even more suitable for use in medical materials.
• m/(n+m) is 0.3 or more.
• Such polysiloxane compounds are even more suitable for use in medical materials.
• the present invention also provides a polymer that is a polymer of the polysiloxane compound described above.
• Such polymers have good compatibility with other compounds that have polymerizable groups such as (meth)acryloxy groups.
• the mass ratio of the polysiloxane compound is 20 mass% or more relative to the total mass of the polymer.
• Such polymers are more likely to exhibit the properties of polysiloxane compounds.
• the present invention also provides a hydrogel or medical material that contains the polymer described above.
• the polymers of the present invention can be suitably used for such applications.
• the present invention also provides a method for producing a polysiloxane compound, comprising the steps of: A compound containing an unsaturated group and a tertiary hydroxyl group at its terminal; An organohydrogenpolysiloxane compound represented by the following general formula (5), (In the formula, each Z is independently an organic group having 1 to 20 carbon atoms, each R is independently a monovalent hydrocarbon group having 1 to 6 carbon atoms, n is an integer from 0 to 200, and m is an integer from 3 to 200, with the proviso that at least one Z is a (meth)acryloxy group.) to obtain a polysiloxane compound represented by the following general formula (1): (In the formula, R' are each independently a monovalent hydrocarbon group having 3 to 20 carbon atoms and a tertiary hydroxyl group at an end, and may contain an ether bond in the middle of the group. Z, R, n, and m are as defined above.)
• This method for producing a polysiloxane compound makes it possible to obtain a polysiloxane compound of the above general formula (1) with high purity.
• This method for producing polysiloxane compounds makes it possible to economically obtain polysiloxane compounds with high purity.
• the content of the polysiloxane compound represented by the general formula (1) is 90% or more.
• the polysiloxane compound of the present invention has a tertiary hydroxyl group at the end of the side chain, and therefore has excellent compatibility with hydrophilic monomers, and when used as a medical material, there is no decrease in transparency, unexpected increase in hardness, or decrease in flexibility. Furthermore, (co)polymers containing repeating units derived from polymerization of the (meth)acryloxy groups of the polysiloxane compound of the present invention have favorable strength.
• the polysiloxane compound of the present invention is useful as a monomer for medical materials.
• the present inventors have conducted extensive research to solve the above problems and have found that a polysiloxane compound containing one or more (meth)acryloxy groups in one molecule and having a tertiary hydroxyl group at the end of a side chain of the polysiloxane compound has excellent compatibility with other hydrophilic monomers. They have also found that a (co)polymer of the polysiloxane compound and a hydrophilic monomer has excellent flexibility.
• the present invention is a polysiloxane compound that contains one or more (meth)acryloxy groups in one molecule and has a tertiary hydroxyl group at the end of the side chain of the polysiloxane compound.
• the present invention relates to a polysiloxane compound containing one or more (meth)acryloxy groups in one molecule, and having a tertiary hydroxyl group at the end of a side chain of the polysiloxane compound.
• the compound has a polysiloxane structure and is characterized by containing a tertiary hydroxyl group at the end of the side chain of the polysiloxane compound.
• this tertiary hydroxyl group becomes a hydrophilic group, which has steric restrictions. This suppresses side reactions during the reaction, and it is presumed that in a polymer ((co)polymer) containing a repeating unit derived from the polymerization of the (meth)acryloxy group of the polysiloxane compound of the present invention, strong hydrogen bonding due to the directionality of the hydrogen bonds is generated, resulting in high strength.
• the polysiloxane compound of the present invention has high compatibility with hydrophilic monomers, and can provide a desirable strength in the derived (co)polymer, without causing an unexpected increase in hardness or decrease in flexibility.
• the polysiloxane compound is preferably one represented by the following general formula (1).
• Z's are each independently an organic group having 1 to 20 carbon atoms
• R's are each independently a monovalent hydrocarbon group having 1 to 6 carbon atoms
• R's are each independently a monovalent hydrocarbon group having 3 to 20 carbon atoms and having a tertiary hydroxyl group at an end, which may contain an ether bond
• n is an integer from 0 to 200
• m is an integer from 3 to 200, with the proviso that at least one Z is a (meth)acryloxy group.
• Z's are each independently an organic group having 1 to 20 carbon atoms, and are preferably represented by the following general formula (2).
• X is a hydrogen atom or a methyl group, and the dashed line represents a bond to the silicon atom.
• R are each independently a monovalent hydrocarbon group having 1 to 6 carbon atoms.
• monovalent hydrocarbon groups include alkyl groups such as methyl, ethyl, propyl, n-butyl, t-butyl, pentyl, and hexyl; cycloalkyl groups such as cyclopentyl and cyclohexyl; and aryl groups such as phenyl.
• R is preferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group.
• R' are each independently a monovalent hydrocarbon group having 3 to 20 carbon atoms and a tertiary hydroxyl group at the end, and may contain an ether bond in the middle of the group. It is preferable that R' is represented by the following general formula (3) or (4): (In general formula (3), k represents an integer of 0 to 5, and in general formulas (3) and (4), the dashed lines represent bonds to the silicon atom.)
• k is an integer from 0 to 5, preferably 0 or 1.
• n is an integer from 0 to 200, and m is an integer from 3 to 200.
• n is an integer from 0 to 100
• m is an integer from 3 to 100
• m/(n+m) is 0.15 or more. More preferably, m/(n+m) is 0.3 or more. Even more preferably, m/(n+m) is 0.3 to 1.0.
• a method for producing the polysiloxane compound represented by the above general formula (1) provides a method for producing a polysiloxane compound, comprising the steps of: A compound containing an unsaturated group and a tertiary hydroxyl group at its terminal; An organohydrogenpolysiloxane compound represented by the following general formula (5), (In the formula, each Z is independently an organic group having 1 to 20 carbon atoms, each R is independently a monovalent hydrocarbon group having 1 to 6 carbon atoms, n is an integer from 0 to 200, and m is an integer from 3 to 200, with the proviso that at least one Z is a (meth)acryloxy group.) and subjecting the above to a hydrosilylation reaction to obtain a polysiloxane compound represented by general formula (1).
• the method for producing a polysiloxane compound of the present invention is characterized by using a compound having an unsaturated group and a tertiary hydroxyl group at the end as a raw material.
• the hydroxyl group is a tertiary hydroxyl group, it is possible to prevent the hydroxyl group from causing an undesirable side reaction in the hydrosilylation reaction. This makes it possible to obtain the polysiloxane compound of the present invention with high purity.
• the hydrosilylation reaction may be carried out according to a conventional method.
• a compound having an unsaturated group and a tertiary hydroxyl group at the end may be added, for example, in an amount of 1 molar equivalent or more, to the organohydrogenpolysiloxane compound represented by the above general formula (5) and reacted.
• the reaction temperature is not particularly limited, but a temperature not exceeding the boiling point of the solvent used is preferable.
• the reaction may be carried out at a temperature of about 0°C to about 150°C.
• the hydrosilylation reaction may be carried out in the presence of a solvent, a hydrosilylation catalyst, or a stabilizer.
• the solvent, hydrosilylation catalyst, and stabilizer may be conventionally known and are not particularly limited.
• the compound having an unsaturated group and a tertiary hydroxyl group at the end to the hydrogensiloxy unit it is preferable to add 1 molar equivalent or more of the compound having an unsaturated group and a tertiary hydroxyl group at the end to the hydrogensiloxy unit. More preferably, it is 1.0 to 3.0 molar equivalents, even more preferably, it is 1.2 to 2.0 molar equivalents, and particularly preferably, it is 1.5 to 2.0 molar equivalents.
• 1 molar equivalent or more of the compound having an unsaturated group and a tertiary hydroxyl group at the end to the hydrogensiloxy unit it is possible to suppress the remaining hydrogensiloxy unit and side reactions.
• a molar equivalent of 3.0 or less is preferable in terms of yield and economy.
• the hydrosilylation catalyst is preferably, for example, a noble metal catalyst, particularly a platinum catalyst derived from chloroplatinic acid.
• a catalyst in which the hydrogen ions of chloroplatinic acid are completely neutralized with sodium bicarbonate to improve the stability of the platinum catalyst is preferable.
• a complex of 1,1,3,3-tetramethyl-1,3-divinyldisiloxane and a sodium bicarbonate neutralized product of chloroplatinic acid Karstead catalyst is more preferable.
• the amount of hydrosilylation catalyst added may be a catalytic amount sufficient to advance the hydrosilylation reaction.
• a complex of 1,1,3,3-tetramethyl-1,3-divinyldisiloxane and chloroplatinic acid neutralized with sodium hydrogen carbonate may be used in an amount that is 1 ppm to 80 ppm in terms of platinum relative to the mass of the organohydrogenpolysiloxane compound represented by the general formula (5) above.
• solvent examples include glycol ether solvents such as methyl cellosolve, ethyl cellosolve, isopropyl cellosolve, butyl cellosolve, propylene glycol monomethyl ether, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, polyethylene glycol monomethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, and polyethylene glycol dimethyl ether; ester solvents such as ethyl acetate, butyl acetate, amyl acetate, ethyl lactate, and methyl benzoate; aliphatic hydrocarbon solvents such as linear hexane, linear heptane, and linear octane; alicyclic hydrocarbon solvents such as cyclohexane and ethylcyclohexane; ketone solvents such as acetone, methyl ethyl ketone,
• the stabilizer examples include phenol-based antioxidants, phosphorus-based antioxidants, amine-based antioxidants, and sulfur-based antioxidants.
• examples of the phenol-based antioxidant include, but are not limited to, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, 4,4-thiobis(3-methyl-6-tert-butylphenol), 2,2′-methylenebis(4-methyl-6-t-butylphenol), phenol resins, and cresol resins.
• phosphorus-based antioxidants include, but are not limited to, tris[2-[[2,4,8,10-tetrakis(1,1-dimethylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-yl]oxy]ethyl]amine, tris[2-[(4,6,9,11-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphepin-2-yl)oxy]ethyl]amine, and ethylbis(2,4-ditert-butyl-6-methylphenyl)phosphite.
• amine-based antioxidant examples include, but are not limited to, tri- or tetra-C1-3 alkylpiperidine or a derivative thereof, bis(2,2,6,6-tetramethyl-4-piperidyl)oxalate, 1,2-bis(2,2,6,6-tetramethyl-4-piperidyloxy)ethane, phenylnaphthylamine, N,N'-diphenyl-1,4-phenylenediamine, N-phenyl-N'-cyclohexyl-1,4-phenylenediamine, etc.
• sulfur-based antioxidant examples include, but are not limited to, dilauryl thiodipropionate, distearyl thiodipropionate, etc.
• the stabilizers may be used alone or in combination of two or more.
• the end point of the reaction can be confirmed by a conventionally known method, for example, by the disappearance of the peaks of the raw material compounds by 1 H-NMR analysis, thin layer chromatography (TLC), high performance liquid chromatography (HPLC), gas chromatography (GC), or the like.
• TLC thin layer chromatography
• HPLC high performance liquid chromatography
• GC gas chromatography
• the product may be purified according to a conventional method.
• the organic layer may be washed with water and then the solvent may be removed to isolate the product.
• reduced pressure distillation or activated carbon treatment may be used.
• 1 molar equivalent of the organohydrogenpolysiloxane compound represented by the above general formula (5), 1.5 molar equivalents of a compound having an unsaturated group and a tertiary hydroxyl group at the end, and a toluene solution of a chloroplatinic acid sodium hydrogen carbonate neutralized product/vinylsiloxane complex (platinum content 0.5 wt%) are added in an amount of 10 ppm in terms of platinum relative to the mass of the organohydrogenpolysiloxane compound, and the mixture is heated and stirred at 80°C. The reaction is completed by reacting for about 6 hours.
• the progress of the reaction can be confirmed by monitoring the compound having an unsaturated group and a tertiary hydroxyl group at the end, or the compound produced, by 1 H-NMR analysis or the like.
• the unreacted raw materials are distilled off under reduced pressure to obtain the polysiloxane compound represented by the above general formula (1).
• the purity (content) of the polysiloxane compound of the present invention can be confirmed, for example, by performing gel permeation chromatography (GPC) measurement.
• the measurement may be performed according to a conventionally known method, and is not particularly limited, but it is preferable to use an eluent that dissolves the polysiloxane compound of the present invention.
• a conventionally known detector for example, a differential refractive index (RI) detector, can be used.
• the purity of the polysiloxane compound can be calculated from the area ratio of the target on the GPC chromatograph. In this case, it is preferable that the content of the polysiloxane compound is 90% or more, and the characteristics of the polysiloxane compound of the present invention are easily exhibited.
• the present invention provides a polymer, which is a polymer of the polysiloxane compound described above.
• the polysiloxane compound of the present invention can provide a polymer containing a repeating unit derived from the (addition) polymerization of the (meth)acryloxy group of the polysiloxane compound.
• the polysiloxane compound of the present invention has good compatibility with other compounds having a polymerizable group such as a (meth)acryloxy group (hereinafter referred to as a polymerizable monomer or a hydrophilic monomer). Therefore, a colorless and transparent copolymer can be obtained by copolymerizing with a polymerizable monomer. It is also possible to polymerize the polysiloxane compound alone.
• the blending ratio of the polysiloxane compound of the present invention is preferably such that the mass ratio of the repeating units derived from the polysiloxane compound of the present invention is 20 mass% or more relative to the total mass of the polymer.
• the mass ratio of the polysiloxane compound is preferably 20 mass% or more relative to the total mass of the polymer.
• the amount of the repeating units derived from the (addition) polymerization of the (meth)acryloxy groups of the polysiloxane compound of the present invention is preferably 20 to 80 mass parts, more preferably 30 to 60 mass parts, per 100 mass parts of the total of the polysiloxane compound of the present invention and the polymerizable (hydrophilic) monomer. If the mass ratio of the repeating units is 20 mass% or more, the properties of the polysiloxane compound of the present invention are easily exhibited.
• polymerizable monomers examples include acrylic monomers such as (meth)acrylic acid, methyl (meth)acrylate, ethyl (meth)acrylate, (poly)ethylene glycol dimethacrylate, polyalkylene glycol mono(meth)acrylate, polyalkylene glycol monoalkyl ether (meth)acrylate, trifluoroethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, and 2,3-dihydroxypropyl (meth)acrylate; acrylic acid derivatives such as N,N-dimethylacrylamide, N,N-diethylacrylamide, N-acryloylmorpholine, and N-methyl (meth)acrylamide; other unsaturated aliphatic or aromatic compounds such as N-vinylpyrrolidone, for example, crotonic acid, cinnamic acid, and vinylbenzoic acid; and siloxane monomers having a polymerizable group such as a (meth)acrylic
• the copolymerization of the polysiloxane compound of the present invention with the other polymerizable monomers may be carried out by a conventionally known method.
• a known polymerization initiator such as a thermal polymerization initiator or a photopolymerization initiator.
• the polymerization initiator include 2-hydroxy-2-methyl-1-phenyl-propan-1-one, azobisisobutyronitrile, azobisdimethylvaleronitrile, benzoyl peroxide, tert-butyl hydroperoxide, cumene hydroperoxide, and 2,2'-azobis(2-methylpropionamidine) dihydrochloride.
• polymerization initiators can be used alone or in combination of two or more.
• the amount of the polymerization initiator is preferably 0.001 to 2 parts by mass, more preferably 0.01 to 1 part by mass, per 100 parts by mass of the total of the polymerization components.
• the polymer containing the repeating unit derived from the polymerization of the (meth)acryloxy group of the polysiloxane compound of the present invention has excellent hydrophilicity. Furthermore, the hydrogel obtained from the polymer has high transparency and strength. Moreover, medical materials can be obtained from the polymer. Therefore, the polysiloxane compound of the present invention is suitable for producing medical materials, such as ophthalmic devices, contact lenses, intraocular lenses, and artificial corneas. There are no particular limitations on the method for producing medical materials using the polymer, and it is sufficient to follow the conventionally known method for producing medical materials. For example, when forming into the shape of a lens such as a contact lens or an intraocular lens, a cutting method or a molding method can be used.
• Measuring device Tosoh HLC-8320 (RI detector) Column: TSK Gelguard Column Super H-H, TSK Gel Super H2500, TSK Gel Super HM-N Temperature: 40°C Eluent: tetrahydrofuran (THF) Flow rate: 0.6 mL/min Sample concentration: 0.3 mass% (THF solution) Injection volume: 50 ⁇ L
• Synthesis Example 2 The same procedure as in Synthesis Example 1 was repeated except that 80.0 g of allyl alcohol was replaced with 141.0 g of allyl glycol, to obtain 145.5 g of an unsaturated compound having a tertiary hydroxyl group represented by the following formula (B).
• 100.0 g of toluene and 0.03 g of a toluene solution of a chloroplatin
• Comparative Examples 1-5 In the method described in JP 2021-073346 A (Example 6), synthesis was performed in the same manner as above, except that the precursor hydrogensiloxane compound was replaced with the hydrogensiloxane compound represented by the above formula (100), to obtain the target product (200P) as a colorless slightly cloudy liquid. GPC measurement was performed and the area of the target product was calculated, and a peak was confirmed in the high molecular weight region, which was 88%.
• unsaturated group-containing compounds that contain tertiary hydroxyl groups at the terminals can produce polysiloxane compounds with higher purity than unsaturated group-containing compounds that contain primary or secondary hydroxyl groups, because side reactions during the hydrosilylation reaction are suppressed in the addition reaction with hydrogensiloxane.
• the target product can also be produced even at a high modification rate.
• the compound can be synthesized with high purity even when the molar ratio of unsaturated compound to hydrogensiloxy units is low, the amount of unsaturated compound used can be reduced, making it superior in terms of yield and economy.
• Examples 2-1 to 2-8 and Comparative Examples 2-1 to 2-3 Production Example of Hydrogel
• HEMA 2-hydroxyethyl methacrylate
• DMA N,N-dimethylacrylamide
• ELDMA ethylene glycol dimethacrylate
• IRG1173 Irgacure 1173
• IPA isopropanol
• UV irradiation was performed using a high-pressure mercury lamp, and the mixture was cured. After curing, the mixture was washed by immersing it in isopropanol, a 50% isopropanol aqueous solution, and deionized water in that order for several seconds, to obtain a hydrogel film. Each physical property value of the obtained film was measured according to the method shown below. The results are shown in Table 1.
• the hydrogels of Examples 2-1 to 2-8 using the polysiloxane compound of the present invention have excellent transparency, excellent elasticity, and maximum elongation.
• the hydrogels of Comparative Examples 2-1 to 2-3 using compounds (200), (201), and (200P) having primary hydroxyl groups or secondary hydroxyl groups as comparative compounds have problems with transparency after curing or hydration, and also have a high elasticity and a low maximum elongation.
• the hydrogels using the polysiloxane compound of the present invention provide medical materials that have beneficial hydrophilicity and sufficient strength and flexibility.
• the polysiloxane compound of the present invention provides a hydrogel having excellent hydrophilicity and strength.
• the polysiloxane compound of the present invention is useful as a monomer for producing medical materials, such as ophthalmic devices, contact lenses, intraocular lenses, artificial corneas, and eyeglass lenses.
• a polysiloxane compound containing one or more (meth)acryloxy groups in one molecule characterized in that the polysiloxane compound has a tertiary hydroxyl group at the end of a side chain thereof.
• [7] The polysiloxane compound according to any one of the above [2] to [6], characterized in that, in the general formula (1), n is an integer of 0 to 100, m is an integer of 3 to 100, and m/(n+m) is 0.15 or more.
• [8] The polysiloxane compound according to the above [7], wherein in the general formula (1), m/(n+m) is 0.3 or more.
• [10] The polymer according to [9] above, characterized in that the mass ratio of the polysiloxane compound is 20 mass% or more based on the total mass of the polymer.
• a method for producing a polysiloxane compound comprising the steps of: A compound containing an unsaturated group and a tertiary hydroxyl group at its terminal; An organohydrogenpolysiloxane compound represented by the following general formula (5), (In the formula, each Z is independently an organic group having 1 to 20 carbon atoms, each R is independently a monovalent hydrocarbon group having 1 to 6 carbon atoms, n is an integer from 0 to 200, and m is an integer from 3 to 200, with the proviso that at least one Z is a (meth)acryloxy group.) by subjecting the above to a hydrosilylation reaction to obtain a polysiloxane compound represented by the following general formula (1): (In the formula, R' are each independently a monovalent hydrocarbon group having 3 to 20 carbon atoms and a tertiary hydroxyl group at an end, and may contain an ether bond in the middle of the group.
• the present invention is not limited to the above-described embodiments.
• the above-described embodiments are merely examples, and anything that has substantially the same configuration as the technical idea described in the claims of the present invention and exhibits similar effects is included within the technical scope of the present invention.

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• 2023
  • 2023-08-07 JP JP2023128873A patent/JP2025024626A/ja active Pending
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  • 2024-06-10 WO PCT/JP2024/020976 patent/WO2025032949A1/ja active Pending

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