JP2010148776A - Medical material - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a medical material which shows antibiotic properties and is transparent and a method of manufacturing the same. <P>SOLUTION: The medical material contains a silicone component containing polymer (A) obtained by polymerizing a monomer composition containing at least one silicone monomer having a hydroxy group and chitosan (B) having a molecular weight of 200-800. In the method of manufacturing the medical material, a molded body consisting of the silicone component containing polymer (A) is immersed in a solution containing the chitosan (B) after the molded body is immersed in a solution containing polyacrylic acid. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to an antibacterial and transparent medical material and a method for producing the same, and the medical material includes an ophthalmic lens, an endoscope, a catheter, an infusion tube, a gas transport tube, a stent, a sheath, It is particularly preferably used for medical devices such as cuffs, tube connectors, access ports, drainage bags, and blood circuits, especially contact lenses, intraocular lenses, and artificial corneas.

  As one of medical materials, a material using a silicone component having excellent oxygen permeability, hydrophilicity, and elasticity has attracted attention.

  For example, Patent Document 1 discloses a silicone hydrogel obtained from a silicone monomer having a hydroxyl group. However, these silicone hydrogels do not have functions such as antibacterial properties.

  On the other hand, Patent Document 2 discloses an antibacterial material in which polymethylmethacrylate, a lens material, is coated on a polyelectrolyte complex gel solution prepared using deacetylated chitosan as a cationic polymer and alginic acid as an anionic polymer. Has been. However, such a material has low oxygen permeability and is not preferable for use as a medical material in a field where oxygen permeability is required, such as a contact lens.

JP 2003-221940 A JP-A-5-117111

  An object of the present invention is to provide a medical material having a good shape, being transparent, and having ultraviolet absorption, antibacterial properties, and the like. The medical material is suitably used for various medical devices, particularly contact lenses, intraocular lenses, artificial corneas, and the like, and is particularly suitable for contact lenses.

In order to achieve the above object, the present invention has the following configuration. That is,
(1) A medical use comprising a silicone component-containing polymer (A) obtained by polymerizing a monomer composition containing at least one silicone monomer having a hydroxyl group, and chitosan (B) having a molecular weight of 200 to 800 material.
(2) The medical material according to (1) above, wherein the silicon atom-containing polymer (A) has a silicon atom content of 5 to 30% by weight.
(3) The medical material as described in (1) or (2) above, wherein the hydroxyl group content in the silicone component-containing polymer (A) is 0.0005 to 0.01 equivalent / g.
(4) The use of the medical material was selected from ophthalmic lenses, endoscopes, catheters, infusion tubes, gas transport tubes, stents, sheaths, cuffs, tube connectors, access ports, drainage bags, and blood circuits. The medical material according to any one of (1) to (3), which is one type of medical device.
(5) A medical material in which the use of the medical material is an ophthalmic lens.
(6) The medical product according to any one of the above (1) to (5), wherein a molded product containing the silicone component-containing polymer (A) is immersed in a solution containing the chitosan (B). Material manufacturing method.
(7) The molded article containing the silicone component-containing polymer (A) is immersed in a solution containing polyacrylic acid and a solution containing the chitosan (B). The manufacturing method of the medical material in any one.
(8) The molded body containing the silicone component-containing polymer (A) is immersed in a solution containing polyacrylic acid and then immersed in a solution containing the chitosan (B). (5) The manufacturing method of the medical material in any one of.

  According to the present invention, a silicone monomer component-containing polymer is immersed in a solution containing chitosan and has a good shape, and even when low molecular weight chitosan, particularly chitosan having a molecular weight of about 200 to 800 is used. Therefore, it is possible to obtain a medical material that is transparent, has high oxygen permeability, and has functions such as antibacterial properties. The medical material is particularly preferably used for various medical devices, particularly contact lenses, intraocular lenses, artificial corneas and the like.

  The medical material of the present invention contains a silicone component-containing polymer (A) obtained by polymerizing a monomer composition containing at least one silicone monomer having a hydroxyl group, and chitosan (B) having a molecular weight of 200 to 800. It is characterized by.

  In the present invention, the silicone monomer represents a compound having a siloxanyl group and a polymerizable unsaturated double bond. The siloxanyl group represents a group having at least one Si—O—Si bond.

  The medical material of the present invention preferably contains 5 to 30% by weight of silicon atoms based on its dry weight. Here, the content of silicon atoms relative to the dry weight of the medical material can be measured by an inductively coupled plasma (ICP) emission spectrometer (preferably a sequential ICP emission spectrometer SPS4000, manufactured by Seiko Instruments Inc.). The measuring method is as follows.

  First, the medical material is in a dry state. In the present invention, the dry state of the medical material means a state where the medical material is vacuum-dried at 40 ° C. for 16 hours. The degree of vacuum in the vacuum drying is 2 hPa or less. Weigh the dried medical material (4-5 mg) in a platinum crucible, add sulfuric acid, and heat ash with a hot plate and burner. The lime is melted with sodium carbonate, water is added and dissolved by heating, and then nitric acid is added to make a constant volume with water. About this solution, the silicon atom was measured by ICP emission spectroscopic analysis, and the content in the medical material was determined.

  If the content of silicon atoms in the medical material of the present invention is too small, sufficient oxygen permeability cannot be obtained, and if it is too large, a transparent medical material cannot be obtained. 10 to 25% by weight is more preferable, and 10 to 20% by weight is most preferable.

  The silicone component-containing polymer constituting the medical material of the present invention is obtained by polymerizing a silicone monomer having a hydroxyl group, and the medical material is transparent even if the hydroxyl group content in the silicone monomer is too little or too much. Therefore, at least one of the silicone monomers preferably has a hydroxyl group of 0.0005 to 0.01 equivalent / g, more preferably 0.0008 to 0.008 equivalent / g. 0.005 equivalent / g is most preferred. The hydroxyl group content in the present invention is determined by various analyzes such as gas chromatography mass spectrometry (GC-MS), high performance liquid chromatography mass spectrometry (HPLC-MS), nuclear magnetic resonance (NMR), infrared spectroscopy (IR) and the like. Can be identified by identifying the structure of the silicone monomer having a hydroxyl group.

  As a suitable example of the silicone monomer used for the medical material of this invention, the silicone monomer of following formula (a), (b) is mentioned.

[In the formulas (a) and (b), k represents an integer of 0 to 100. b represents an integer of 1 to 3.
R ¹¹ represents H or a methyl group.
R ¹² and ^{R 13} each independently represent a substituent selected from an alkyl group and a phenyl group having 1 to 18 carbon atoms.
R ¹⁴ represents a substituent selected from an alkyl group having 1 to 6 carbon atoms and a phenyl group.
R ¹⁵ and R ¹⁶ each independently represent a substituent selected from an alkyl group having 1 to 18 carbon atoms and a phenyl group. ]
If k is too small, the oxygen permeability of the obtained medical material is lowered, and if it is too large, it tends to be difficult to obtain a transparent medical material. Therefore, 1 to 30 is more preferable, and 1 to 20 is more preferable. Preferably, it is 2-10. When b is too small, the oxygen permeability of the obtained medical material is lowered, and when it is too large, the elastic modulus tends to be too high.

R ¹¹ represents H or a methyl group, and is preferably a methyl group from the viewpoint of chemical stability of the obtained medical material.

R ¹² and R ¹³ each independently represent a substituent selected from an alkyl group having 1 to 18 carbon atoms and a phenyl group, and the number of carbon atoms is preferred in that a higher oxygen-permeable polymer is obtained. 1-4 alkyl groups, most preferred is a methyl group.

R ¹⁴ represents a substituent selected from an alkyl group having 1 to 6 carbon atoms and a phenyl group, and an alkyl group having 1 to 4 carbon atoms is preferable in that a higher oxygen-permeable polymer is obtained. In view of ease of production, methyl and butyl groups are most preferred.

R ¹⁵ and R ¹⁶ each independently represents a substituent selected from an alkyl group having 1 to 18 carbon atoms and a phenyl group, but preferably has a carbon number in that a higher oxygen-permeable polymer is obtained. In view of ease of production, it is most preferably a methyl group.

  If the content of the silicone monomer in the medical material of the present invention is too small, sufficient oxygen permeability cannot be obtained, and if it is too large, a transparent medical material cannot be obtained. It is appropriately selected so as to be in the range of 30% by weight.

  Moreover, this invention provides the manufacturing method which obtains a medical material by immersing the molded object containing the said silicone component containing polymer (A) in the solution containing chitosan.

  The chitosan used in the present invention is preferably biocompatible chitosan. In the present invention, the biocompatibility means a property that is safe and non-toxic to a living body, and preferably further has a property that is easily compatible with a living body.

  Chitosan may be derived from a natural product, or may be chemically or enzymatically synthesized or prepared by a semi-synthetic method, if necessary, or may be a functional group of these materials modified. The average molecular weight of chitosan used in the present invention is average in terms of excellent durability of hydrophilization performance, little influence on medical materials, and no change in specifications of medical materials such as shape and appearance. Those having a molecular weight of 200 to 800 are preferred, and those having an average molecular weight of 500 to 700 are particularly preferred from the viewpoints of the viscosity of the solution, handling properties, and the like.

  In the present invention, the solvent used in the solution containing chitosan may be any solvent as long as it can uniformly dissolve chitosan, but is preferably water, lactic acid (mixture of D-form and L-form), and lactic acid aqueous solution.

  If the concentration of the solution containing chitosan used in the present invention is too low, it does not exhibit antibacterial properties, and if it is too high, the solubility, viscosity, handleability, etc. of chitosan in the solution deteriorate, so 0.5 wt% to 5 wt%. A chitosan aqueous solution is particularly preferred.

  The medical material of the present invention can be obtained by immersing a molded body containing the silicone component-containing polymer in a solution containing chitosan. The immersion time is typically 1 to 2 hours.

  Moreover, in order to improve the hydrophilic effect of the medical material of the present invention, it may be immersed in a solution containing polyacrylic acid.

  In the present invention, the solvent used in the solution containing polyacrylic acid may be any solvent as long as it can dissolve polyacrylic acid uniformly, but is preferably water.

  In the present invention, the concentration of the solution containing polyacrylic acid is preferably 1.2% by weight to 3% by weight from the viewpoint of the viscosity, solubility, handleability, and the like of the solution.

  The medical material of the present invention is a method of immersing a molded body containing the above-mentioned silicone component-containing polymer (A) in a solution containing polyacrylic acid and then immersing it in a solution containing the above-mentioned chitosan (B), chitosan (B) It can be obtained by dipping in a solution containing polyacrylic acid and then dipping in a solution containing polyacrylic acid, or by dipping simultaneously in a solution containing polyacrylic acid and chitosan (B). The method of immersing in the solution containing chitosan (B) after immersing in the solution containing acrylic acid is preferable. The immersion time in the solution containing polyacrylic acid is typically 1 to 2 hours.

  The medical material of the present invention may contain an ultraviolet absorber, a pigment, a colorant and the like. Moreover, you may contain in the form which copolymerized the ultraviolet absorber which has a polymeric group, a pigment | dye, and a coloring agent.

  When the polymer containing the silicone component used for the medical material of the present invention is obtained by polymerization, a thermal polymerization initiator typified by a peroxide or an azo compound or a photopolymerization initiator is added to facilitate the polymerization. It is preferable. When performing thermal polymerization, a thermal polymerization initiator having an optimum decomposition characteristic for a desired reaction temperature is selected and used. In general, azo initiators and peroxide initiators having a 10-hour half-life temperature of 40 ° C to 120 ° C are suitable. Examples of the photopolymerization initiator include carbonyl compounds, peroxides, azo compounds, sulfur compounds, halogen compounds, and metal salts. These polymerization initiators are used alone or in combination, and are used in an amount of up to about 1% by weight.

  When the silicone component-containing polymer used for the medical material of the present invention is obtained by polymerization, a polymerization solvent can be used. Various organic and inorganic solvents can be used as the solvent. For example, water, methanol, ethanol, propanol, 2-propanol, butanol, tert-butanol, various alcohol solvents such as tert-amyl alcohol, various aromatic hydrocarbon solvents such as benzene, toluene, xylene, hexane , Heptane, octane, decane, petroleum ether, kerosene, ligroin, paraffin and other aliphatic hydrocarbon solvents, acetone, methyl ethyl ketone, methyl isobutyl ketone and other ketone solvents, ethyl acetate, butyl acetate, methyl benzoate, phthalate Various ester solvents such as dioctyl acid, ethylene glycol diacetate, diethyl ether, tetrahydrofuran, dioxane, ethylene glycol dialkyl ether, diethylene glycol dialkyl ether, triethylene glycol These are various glycol ether solvents such as cold dialkyl ether, tetraethylene glycol dialkyl ether, polyethylene glycol dialkyl ether, polyethylene glycol-polypropylene glycol block copolymer, polyethylene glycol-polypropylene glycol random copolymer, and these are used alone or in combination. Can be used. Among these, alcohol solvents and glycol ether solvents are preferable in that the solvent can be easily removed from the obtained medical material by washing with water.

  When the use of the medical material of the present invention is an ophthalmic lens, the following methods can usually be used as the polymerization method and molding method. For example, a method of once forming a round bar or a plate and processing it into a desired shape by cutting or the like, a mold polymerization method, a spin casting method, or the like.

  As an example, a case where an ophthalmic lens made of the medical material of the present invention is obtained by a mold polymerization method will be described below.

  The monomer composition is filled in the gap between two molds having a lens shape. Then, photopolymerization or thermal polymerization is performed to form a lens shape. The mold is made of resin, glass, ceramics, metal, etc., but in the case of photopolymerization, an optically transparent material is used, and usually resin or glass is used. In the case of producing a medical material, in many cases, a void is formed by two opposing molds, and the void is filled with the monomer composition. Subsequently, the mold in which the voids are filled with the monomer composition is irradiated with actinic rays such as ultraviolet rays or placed in an oven or a liquid bath and heated to polymerize the monomer. There may be a method of using both in combination, such as heat polymerization after photopolymerization, or conversely photopolymerization after heat polymerization. In the case of photopolymerization, it is common to irradiate light containing a large amount of ultraviolet light using, for example, a mercury lamp or insect trap as a light source for a short time (usually 1 hour or less). When thermal polymerization is performed, the temperature is gradually raised from around room temperature, and the temperature is increased to 60 ° C. to 200 ° C. over several hours to several tens of hours, so that the optical uniformity and quality of the polymer are maintained. And is preferably used to improve reproducibility.

  The medical material of the present invention can be modified by various methods. When the application is an ophthalmic lens, it is preferable to perform a modification treatment that improves the water wettability of the surface.

  Specific reforming methods include electromagnetic vapor (including light) irradiation, plasma irradiation, chemical vapor deposition treatment such as vapor deposition and sputtering, heating, base treatment, acid treatment, use of other appropriate surface treatment agents, and these Can be mentioned. Among these reforming means, simple and preferred are base treatment and acid treatment.

  Examples of the base treatment and the acid treatment include a method in which a molded product is brought into contact with a basic or acidic solution, and a method in which a molded product is brought into contact with a basic or acidic gas. More specific methods include, for example, a method of immersing a molded product in a basic or acidic solution, a method of spraying a basic or acidic solution or basic or acidic gas on the molded product, or a basic or acidic solution on a molded product. Examples of the method include a method of applying the coating with a spatula, a brush, etc., and a basic or acidic solution applied to the molded product by a spin coating method or a dip coating method. The most simple method for obtaining a large modification effect is a method of immersing a molded article in a basic or acidic solution.

  Although the temperature at the time of immersing a medical material in a basic or acidic solution is not specifically limited, Usually, it is performed within a temperature range of about −50 ° C. to 300 ° C. Considering workability, a temperature range of −10 ° C. to 150 ° C. is more preferable, and −5 ° C. to 60 ° C. is most preferable.

  The optimum time for immersing the medical material in the basic or acidic solution varies depending on the temperature, but is generally preferably within 100 hours, more preferably within 24 hours, and most preferably within 12 hours. If the contact time is too long, not only the workability and productivity are deteriorated, but also adverse effects such as a decrease in oxygen permeability and a decrease in mechanical properties may occur.

  High molecular weights such as alkali metal hydroxides, alkaline earth metal hydroxides, various carbonates, various borates, various phosphates, ammonia, various ammonium salts, various amines, polyethyleneimine, and polyvinylamine as bases A base or the like can be used. Of these, alkali metal hydroxides are most preferred because of their low cost and great treatment effect.

  As the acid, various inorganic acids such as sulfuric acid, phosphoric acid, hydrochloric acid and nitric acid, various organic acids such as acetic acid, formic acid, benzoic acid and phenol, and various high molecular weight acids such as polyacrylic acid and polystyrenesulfonic acid can be used. . Among these, a high molecular weight acid is most preferable because it has a large treatment effect and little adverse effect on other physical properties.

  As the solvent for the basic or acidic solution, various inorganic and organic solvents can be used. For example, water, methanol, ethanol, propanol, 2-propanol, butanol, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, various alcohols such as glycerin, various aromatic carbonization such as benzene, toluene, xylene Various aliphatic hydrocarbons such as hydrogen, hexane, heptane, octane, decane, petroleum ether, kerosene, ligroin, paraffin, various ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, butyl acetate, methyl benzoate, phthalate Various esters such as dioctyl acid, diethyl ether, tetrahydrofuran, dioxane, ethylene glycol dialkyl ether, diethylene glycol dialkyl ether Ter, triethylene glycol dialkyl ether, tetraethylene glycol dialkyl ether, various ethers such as polyethylene glycol dialkyl ether, dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, dimethylimidazolidinone, hexamethylphosphoric triamide, And various aprotic polar solvents such as dimethyl sulfoxide, halogen solvents such as methylene chloride, chloroform, dichloroethane, trichloroethane, and trichloroethylene, and fluorocarbon solvents. Of these, water is most preferable from the viewpoints of economy, ease of handling, chemical stability, and the like. As the solvent, a mixture of two or more kinds of substances can also be used.

  The basic or acidic solution used in the present invention may contain components other than the basic or acidic substance and the solvent.

  A medical material can remove a basic or acidic substance by washing after base treatment or acid treatment.

  As the cleaning solvent, various inorganic and organic solvents can be used. For example, water, methanol, ethanol, propanol, 2-propanol, butanol, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, various alcohols such as glycerin, various aromatic carbonization such as benzene, toluene, xylene Various aliphatic hydrocarbons such as hydrogen, hexane, heptane, octane, decane, petroleum ether, kerosene, ligroin, paraffin, various ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, butyl acetate, methyl benzoate, phthalate Various esters such as dioctyl acid, diethyl ether, tetrahydrofuran, dioxane, ethylene glycol dialkyl ether, diethylene glycol dialkyl ether Ter, triethylene glycol dialkyl ether, tetraethylene glycol dialkyl ether, various ethers such as polyethylene glycol dialkyl ether, dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, dimethylimidazolidinone, hexamethylphosphoric triamide, And various aprotic polar solvents such as dimethyl sulfoxide, halogen solvents such as methylene chloride, chloroform, dichloroethane, trichloroethane, and trichloroethylene, and fluorocarbon solvents.

  As the washing solvent, a mixture of two or more kinds of solvents can also be used. The cleaning solvent may contain components other than the solvent, such as inorganic salts, surfactants, and cleaning agents.

  The modification treatment as described above may be performed on the entire medical material, or may be performed on only a part of the medical material, for example, only on the surface. When the modification treatment is performed only on the surface, only the wettability of the surface can be improved without greatly changing the properties of the entire medical material.

  In the medical material of the present invention, a method of combining the silicone component-containing polymer and the modified chitosan includes a method of immersing the silicone component-containing polymer in a solution containing the modified chitosan. When the silicone component-containing polymer is immersed in a solution containing modified chitosan, if the immersion time is too short, the modified chitosan will not adsorb to the medical material, and if it is too long, the shape and appearance of the medical material may be affected. From 1 hour to 2 hours is preferable.

  Moreover, you may immerse in the solution containing chitosan after said modification | reformation process.

  The oxygen permeability of the medical material of the present invention was measured in water at 35 ° C. using a Kaken type film oxygen permeability meter manufactured by Rika Seiki Kogyo. The measurement was performed according to the method described in paragraphs 293 to 294 of US Patent Publication No. US2008 / 0081894.

The oxygen permeability coefficient of the medical material of the present invention is preferably 70 × 10 ⁻¹¹ (cm ² / sec) mLO ₂ / (mL · hPa) or more in terms of quality when the use is an ophthalmic lens.

  The transparency of the medical material of the present invention is such that, when the application is an ophthalmic lens, the total light transmittance in a water-containing state of the ophthalmic lens is preferably 70% or more, more preferably 80% or more. Preferably, 82% or more is most preferable. The total light transmittance is measured as follows.

  The total light transmittance of the ophthalmic lens is measured using an SM color computer (model SM-7-CH, manufactured by Suga Test Instruments Co., Ltd.). As the sample, an ophthalmic lens whose center is cut to a width of 5 mm and lightly wiped off is used. The thickness is measured using an ABC Digimatic Indicator (ID-C112, manufactured by Mitutoyo Corporation), and a thickness of 0.14 to 0.15 mm is used for the measurement.

  The wettability of the medical material of the present invention is determined by immersing the medical material in purified water for 10 minutes, pinching the medical material with tweezers and pulling it up vertically, visually observing the state of the surface water film, It can be evaluated by measuring the time until the film breaks. When the use of the medical material is an ophthalmic lens, in terms of its quality, it is preferable that the entire surface of the ophthalmic lens is evenly wet even after 20 seconds or more after being pulled out from purified water.

  Since the medical material of the present invention is obtained by immersing it in a solution containing chitosan, it can exhibit antibacterial properties. The antibacterial property of the medical material of the present invention can be evaluated by a test method such as JIS Z 2801: 2000 “Antimicrobial Processed Product—Antimicrobial Test Method / Antimicrobial Effect” 5.2 Plastic Product. The antibacterial property is the difference between the average value of the three logarithmic bacteria concentration and the average of the three logarithmic bacteria concentration of the control not containing zinc oxide when the number of bacteria of 3 samples was measured with Pseudomonas aeruginosa. If it is within 0.4, it is considered that there is no increase / decrease, and if it is −0.4 or less, it is judged that there is an antibacterial effect. More preferably, it is −2 or less, and most preferably −3 or less.

  The medical material of the present invention includes medical devices such as ophthalmic lenses, endoscopes, catheters, infusion tubes, gas transport tubes, stents, sheaths, cuffs, tube connectors, access ports, drainage bags, and blood circuits. It is particularly suitable for ophthalmic lenses such as contact lenses, intraocular lenses, and artificial corneas.

  Hereinafter, the present invention will be specifically described by way of examples, but the present invention is not limited thereto.

Example 1
The following formula (c)

(22.3 parts by weight, hydroxyl group content 0.0053 equivalent / g), N, N-dimethylacrylamide (24.2 parts by weight), and the following formula (d)

(33.6 parts by weight, hydroxyl group content 0.0055 equivalent / g), photoinitiator Irgacure 1850 (1.2 parts by weight), 2-hydroxyethyl methacrylate (9.1 parts by weight) ), Triethylene glycol dimethacrylate (0.6 parts by weight), the following formula (e)

And tert-amyl alcohol (17.2 parts by weight) were mixed and stirred. A uniform and transparent monomer mixture was obtained. The monomer mixture was degassed under an argon atmosphere. In a glove box in a nitrogen atmosphere, a lens mixture was filled with a monomer mixture and cured by light irradiation (Toshiba FL6D, 8.4 kilolux, 20 minutes) to obtain a lens. The obtained lens is immersed in a 60% by weight isopropanol (IPA) aqueous solution at 60 ° C. for 30 minutes, peeled off from the mold, and further immersed in an 80% by weight IPA aqueous solution at 60 ° C. for 2 hours to extract impurities such as residual monomers. 50% by weight IPA aqueous solution, 25% by weight IPA aqueous solution, and water were gradually hydrated for about 30 minutes in a stepwise reduced IPA concentration. The vial was immersed in a borate buffer solution (pH 7.1 to 7.3) in a 5 mL vial, and the vial was placed in an autoclave and boiled at 120 ° C. for 30 minutes. After boiling the lens with ultrapure water, the following formula (f)

Was immersed in a 5% aqueous solution of chitosan (average molecular weight 669) represented by
The content of silicon atoms with respect to the dry weight of the obtained lens is 12.3% by weight, and the oxygen transmission coefficient is 72 × 10 ⁻¹¹ (cm ² / sec) mLO ₂ / (mL · hPa), which is transparent and has no turbidity. A lens was obtained. The wettability evaluation was 5 seconds.

Example 2
Before the lens after boiling treatment was immersed in a 5% aqueous solution of chitosan (f) for 2 hours, the lens was immersed in a 3% polyacrylic acid aqueous solution for 2 hours and the same experiment as in Example 1 was performed. The content of silicon atoms with respect to the dry weight of the powder is 12.3% by weight, and the oxygen permeability coefficient is 72 × 10 ⁻¹¹ (cm ² / sec) mLO ₂ / (mL · hPa). In this case, the entire lens surface was evenly wet even after 20 seconds had elapsed, making it suitable as a contact lens.

Comparative Example 1
An experiment similar to Example 1 and Example 2 was performed using chitosan having an average molecular weight of 1000 instead of chitosan (f). However, a uniform chitosan aqueous solution could not be obtained, and the lenses in Examples and Example 2 were not obtained. It was not possible to produce a lens similar to.

Comparative Example 2
Instead of the silicone monomers (c) and (d), the silicone monomer having no hydroxyl group is represented by the following formula (g)

An experiment similar to that of Example 1 was conducted using [FM-0771 manufactured by Chisso Corporation, an average value of q of about 10]. However, a uniform polymerization stock solution was not obtained, and a lens could not be produced.

Comparative Example 3
Silicone monomer having no hydroxyl group instead of silicone monomer (c), (d)

The same experiment as in Example 1 was carried out using this, but a uniform polymerization stock solution could not be obtained and a lens could not be produced.

Example 3 Antibacterial Evaluation Instead of the mold of Example 1, a 100 μm thick paraffin between two 10 cm square and 3 mm thick glass plates (one of which is attached with an aluminum seal so that it can be easily peeled). A film having a composition similar to that of Example 1 was prepared by using a film obtained by cutting out the central portion of the film and sandwiching it as two spacers. Three pieces of the obtained film cut into 3 cm squares were prepared, and JIS Z 2801: 2000 “Antimicrobial Processed Products-Antimicrobial Test Methods / Antimicrobial Effects” 5.2 Contact lens use based on test methods such as plastic products Antibacterial evaluation was performed against Pseudomonas aeruginosa NBRC 13275, which is one of the representative bacteria sometimes seen. As a result, the average difference in the logarithmic bacteria concentration relative to the control was −3.5, and high antibacterial properties could be confirmed.

Example 4
The same antibacterial evaluation as in Example 3 was performed with the same composition as in Example 2. As a result, the average difference of the logarithmic bacteria concentration with respect to the control was −4.6, and high antibacterial properties could be confirmed.

  The present invention relates to a medical material, and the medical material is particularly preferably used for contact lenses, intraocular lenses, artificial corneas and the like.

Claims (8)

A medical material comprising a silicone component-containing polymer (A) obtained by polymerizing a monomer composition containing at least one silicone monomer having a hydroxyl group, and chitosan (B) having a molecular weight of 200 to 800. The medical material according to claim 1, wherein the content of the silicone component-containing polymer (A) is 5 to 30% by weight. The medical material according to claim 1 or 2, wherein a content of a hydroxyl group in the silicone component-containing polymer (A) is 0.0005 to 0.01 equivalent / g. The medical material is used for one kind selected from ophthalmic lenses, endoscopes, catheters, infusion tubes, gas transport tubes, stents, sheaths, cuffs, tube connectors, access ports, drainage bags, and blood circuits. It is a medical instrument, The medical material in any one of Claims 1-3. The medical material according to any one of claims 1 to 3, wherein the medical material is used for an ophthalmic lens. The method for producing a medical material according to any one of claims 1 to 5, wherein the molded body containing the silicone component-containing polymer (A) is immersed in a solution containing the chitosan (B). The medical product according to any one of claims 1 to 5, wherein the molded product containing the silicone component-containing polymer (A) is immersed in a solution containing polyacrylic acid and a solution containing the chitosan (B). Method of manufacturing materials. The medical use according to any one of claims 1 to 5, wherein the molded body comprising the silicone component-containing polymer (A) is immersed in a solution containing polyacrylic acid and then immersed in a solution containing the chitosan (B). Material manufacturing method.