Classifications

• • 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
  • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups

Definitions

• the present invention relates to a novel polymerizable carbosiloxane dendron and a polymeric compound containing the carbosiloxane dendron as a constituent component. More specifically, the polymerizable carbosiloxane dendron is a novel polymerizable carbosiloxane dendron having a dicarbonyl residue between a polymerizable functional group and the dendron structure.
• Dendrimers are highly branched structures that radiate from a single nucleus, with the number of branching points increasing from the core toward the surface. They have unique properties such as low viscosity, high reactivity, high solubility, and low glass transition temperature, and are therefore attracting attention for their potential applications.
• Dendrons are wedge-shaped segments of monodisperse dendrimers that have multiple terminal groups and a highly reactive functional group in the center, and like dendrimers, their applications are attracting attention.
• organosilicon dendrimers or dendrons include carbosiloxanes that have a highly branched structure in which siloxane bonds and silalkylene bonds are arranged alternately around a polysiloxane structure (see, for example, Patent Document 1), and carbosiloxanes that have polymerizable functional groups in the molecule (see, for example, Patent Document 2).
• the carbosiloxane in Patent Document 1 has a dendrimer structure, it does not have a polymerizable functional group in the molecule, and therefore does not have copolymerizability with other copolymerizable compounds (polymerizable monomers).
• the carbosiloxane in Patent Document 2 has a dendron structure and has a polymerizable functional group in the molecule, it does not have a hydrophilic group, and therefore has low compatibility with other copolymerizable hydrophilic compounds (hydrophilic monomers).
• the carbosiloxane dendrimer disclosed in Patent Document 1 does not have a polymerizable functional group and therefore cannot be used as a constituent.
• the carbosiloxane dendron disclosed in Patent Document 2 has low compatibility with hydrophilic monomers, so a homogeneous monomer mixture cannot be obtained and cannot be subjected to a sufficient copolymerization reaction, resulting in a problem that a hydrogel cannot be formed, or even if it can be formed, a good hydrogel without white turbidity cannot be formed. Therefore, the range of application of the polymerizable monomer that is a constituent of the polymer compound is limited, and the range of application to compositions as functional materials is limited, resulting in a problem in versatility.
• the problem that the present invention aims to solve is to provide a novel polymerizable carbosiloxane dendron and a polymeric compound, particularly a hydrogel, that contains the polymerizable carbosiloxane dendron as a component, which is expected to improve versatility in functional materials due to its excellent compatibility and copolymerizability with copolymerizable hydrophilic compounds.
• the inventors focused on the linker structure that connects the polymerizable functional group and the dendron structure within the molecule. They then thought that by introducing a polar group into the linker structure, it might be possible to improve the compatibility and copolymerizability between the compounds when obtaining a polymer compound that contains a polymerizable carbosiloxane dendron and another copolymerizable compound as a constituent component.
• X-L-D In the general formula (1), X is a (meth)acryloyloxyalkyl residue represented by the following general formula (2): (In general formula (2), R1 represents a hydrogen atom or a methyl group, and a represents an integer of 1 to 4. * represents a bonding site between general formula (2) and the following general formula (3).) L is a dicarbonyl residue represented by the following general formula (3), and (In general formula (3), Y represents an alkylene group or a phenylene group having 1 to 8 carbon atoms.
• D is a carbosiloxane dendron represented by the following general formula (4):
• Z represents O or NH
• b represents an integer of 1 to 5
• c represents an integer of 2 to 5
• R 2 to R 5 each independently represent an alkyl group having 1 to 4 carbon atoms
• R 6 represents an alkyl group having 1 to 4 carbon atoms or a substituted alkyl group represented by the following general formula (5)
• g represents an integer of 2 to 3
• R 18 represents a methyl group.
• * represents a bonding site between general formula (4) and the above general formula (3).
• f is an integer of 2 to 5
• R7 is a hydrogen atom, a linear or branched alkyl group having 1 to 5 carbon atoms, a hydroxyalkyl group, or a silyl group represented by the following general formula (6).
• * is a bonding site between general formula (5) and the above general formula (4).
• R 8 to R 10 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. * represents the bonding site between general formula (6) and the above general formula (5).
• D is a carbosiloxane dendron represented by the following general formula (7).
• Z represents O or NH
• b represents an integer of 1 to 5
• d and e each independently represent an integer of 2 to 5
• R 11 to R 16 each independently represent an alkyl group having 1 to 4 carbon atoms
• R 17 represents an alkyl group having 1 to 4 carbon atoms or a substituted alkyl group represented by the above general formula (5)
• h represents an integer of 2 to 3
• R 19 represents a methyl group.
• the polymerizable carbosiloxane dendron is represented by the formula: [2] The polymerizable carbosiloxane dendron according to [1], wherein in the general formula (2), R 1 is a methyl group and a is an integer of 2. [3] The polymerizable carbosiloxane dendron according to [1], wherein in the general formula (3), Y is an alkylene group having 2 carbon atoms. [4] The polymerizable carbosiloxane dendron according to [1], wherein in the general formula (4), R 2 to R 5 are methyl groups.
• polymerizable carbosiloxane dendron according to [1], wherein the polymerizable carbosiloxane dendron is represented by the following formula: [12] A polymer compound comprising, as constituent components, the polymerizable carbosiloxane dendron according to any one of [1] to [11] and a compound copolymerizable with the polymerizable carbosiloxane dendron. [13] The polymer compound according to [12], wherein the compound copolymerizable with the polymerizable carbosiloxane dendron is at least one hydrophilic compound copolymerizable with the polymerizable carbosiloxane dendron.
• a novel polymerizable carbosiloxane dendron can be provided that has excellent compatibility and copolymerizability with copolymerizable hydrophilic compounds by having a dicarbonyl residue between a polymerizable functional group and a dendron structure in the molecule, and is therefore expected to improve versatility in functional materials.
• the polymerizable carbosiloxane dendron of the present invention has improved compatibility and copolymerizability with copolymerizable hydrophilic compounds, so that when a hydrogel is formed, which is a polymer compound having at least the polymerizable carbosiloxane dendron of the present invention and a copolymerizable hydrophilic compound as its constituents, a transparent and good hydrogel can be formed. Therefore, the range of polymerizable monomers that are constituents of the polymer compound is expanded, and the versatility of the composition as a functional material is improved. As a result, it becomes possible to obtain a variety of hydrogels that have both the characteristic properties of the dendron and the desired hydrogel properties, and new applications of hydrogels are also expected.
• to means a range that includes the numerical values before and after it, for example, "0% to 100%” means a range that is equal to or greater than 0% and equal to or less than 100%.
• “More than” and “less than” mean a lower limit and an upper limit, respectively, without including the numerical value before it, for example, “more than 1” means a numerical value greater than 1, and "less than 100” means a numerical value less than 100.
• the number of digits in an integer value is the same as the number of significant digits. For example, 1 has one significant digit, and 10 has two significant digits. Also, the number of digits after the decimal point in a decimal value is the same as the number of significant digits. For example, 0.1 has one significant digit, and 0.10 has two significant digits.
• polymerizable carbosiloxane dendron which is one embodiment of the present invention
• polymeric compound containing the polymerizable carbosiloxane dendron as a component are described in detail below, but the technical scope of the present invention is not limited to the items in this section, and the present invention can take various forms as long as it achieves its objectives.
• the polymerizable carbosiloxane dendron of one embodiment of the present invention is represented by the following general formula (1).
• X is a (meth)acryloyloxyalkyl residue represented by the following general formula (2):
• R1 represents a hydrogen atom or a methyl group
• a represents an integer of 1 to 4.
• * represents a bonding site between general formula (2) and the following general formula (3).
• a is an integer of 1 to 4, and examples of the group represented by --(CH 2 ) a -- include linear hydrocarbon groups having 1 to 4 carbon atoms.
• L is a dicarbonyl residue represented by the following general formula (3).
• the linker (L) is a dicarbonyl residue, so that the dendron has excellent compatibility and copolymerizability with copolymerizable compounds, particularly with copolymerizable hydrophilic compounds.
• Y represents an alkylene group or a phenylene group having 1 to 8 carbon atoms.
• * represents a bonding site between general formula (3) and general formula (2) above, and a bonding site between general formula (3) and general formula (4) or general formula (7) below.
• L include dicarbonyl residues of malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, phthalic acid, isophthalic acid, terephthalic acid, and the like.
• the dicarbonyl residues of malonic acid, succinic acid, glutaric acid, and adipic acid, in which Y has 1 to 4 carbon atoms are preferably used.
• D is a carbosiloxane dendron moiety represented by the following general formula (4) or the following general formula (7).
• Z represents O or NH
• b represents an integer of 1 to 5
• c represents an integer of 2 to 5
• R 2 to R 5 each independently represent an alkyl group having 1 to 4 carbon atoms
• R 6 represents an alkyl group having 1 to 4 carbon atoms or a substituted alkyl group represented by the following general formula (5)
• g represents an integer of 2 to 3
• R 18 represents a methyl group.
• * represents the bonding site between general formula (4) and the above general formula (3).
• f is an integer of 2 to 5
• R7 represents a hydrogen atom, a linear or branched alkyl group having 1 to 5 carbon atoms, a hydroxyalkyl group, or a silyl group represented by the following general formula (6): * represents the bonding site between general formula (5) and the above general formula (4).
• R 8 to R 10 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. * represents the bonding site between general formula (6) and the above general formula (5).
• Z represents O or NH
• b represents an integer of 1 to 5
• d and e each independently represent an integer of 2 to 5
• R 11 to R 16 each independently represent an alkyl group having 1 to 4 carbon atoms
• R 17 represents an alkyl group having 1 to 4 carbon atoms or a substituted alkyl group represented by general formula (5) above
• h represents an integer of 2 to 3
• R 19 represents a methyl group.
• * represents the bonding site between general formula (7) and general formula (3) above.
• R 2 to R 5 or R 11 to R 16 may all be different substituents, or two to four, or two to six, of these may be the same substituent.
• Examples of the alkyl group represented by R 2 to R 5 or R 11 to R 16 include saturated aliphatic hydrocarbon groups having 1 to 4 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group.
• saturated aliphatic hydrocarbon groups having 1 to 4 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group.
• a methyl group or an ethyl group is more preferable in the present invention.
• R 6 and R 17 are each an alkyl group
• examples of such groups include saturated aliphatic hydrocarbon groups having 1 to 4 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group.
• a methyl group or an ethyl group is more preferable in the present invention.
• examples of the alkyl group include a methoxyethyl group, an ethoxyethyl group, a methoxypropyl group, an ethoxypropyl group, a hydroxymethoxyethyl group, a 2-hydroxyethoxyethyl group, a 3-hydroxypropoxyethyl group, a hydroxymethoxypropyl group, a 2-hydroxyethoxypropyl group, a 3-hydroxypropoxypropyl group, a trimethylsiloxyethyl group, a triethylsiloxyethyl group, a trimethylsiloxypropyl group, and a triethylsiloxypropyl group.
• the 2-hydroxyethoxyethyl group and the trimethylsiloxyethyl group are preferred.
• Examples of the alkyl group represented by R 8 to R 10 include saturated aliphatic hydrocarbon groups having 1 to 3 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, and an isopropyl group.
• saturated aliphatic hydrocarbon groups having 1 to 3 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, and an isopropyl group.
• a methyl group or an ethyl group is more preferred in the present invention.
• polymerizable carbosiloxane dendron represented by general formula (1) include, but are not limited to, the polymerizable carbosiloxane dendrons (1-1) to (1-5) represented by the following formulas.
• the method for producing the polymerizable carbosiloxane dendron is not particularly limited, but examples include the method described in the Examples below, and a method in which the method is appropriately modified to obtain the desired polymerizable carbosiloxane dendron.
• the polymer compound of one embodiment of the present invention can be formed by subjecting a polymerizable carbosiloxane dendron of general formula (1) to a copolymerization reaction, either alone or in combination of two or more types, and a compound copolymerizable therewith.
• the preferred amount of the polymerizable carbosiloxane dendron represented by general formula (1) in the polymer compound of one embodiment of the present invention is not particularly limited, but is, for example, 0.1 to 75 mass % relative to the total amount of the polymer compound, preferably 0.3 to 70 mass %, and more preferably 0.5 to 65 mass %. If the amount of the polymerizable carbosiloxane dendron of general formula (1) is less than 0.1 mass %, the effect of the dendron structure is unlikely to be expressed in the resulting polymer compound. If the amount of the polymerizable carbosiloxane dendron of general formula (1) exceeds 75 mass %, the resulting polymer compound is likely to become cloudy or have a reduced strength, which is not preferred.
• the compound copolymerizable with the polymerizable carbosiloxane dendron of general formula (1) is not particularly limited as long as it can be a monomer component as is commonly known, but for example, a copolymerizable hydrophilic compound is preferably used. Since the polymerizable carbosiloxane dendron of general formula (1) has a dicarbonyl residue introduced as a polar group, the polymer compound obtained by using the copolymerizable hydrophilic compound has excellent compatibility and copolymerizability with the copolymerizable hydrophilic compound, and it is possible to obtain a polymer compound that forms a transparent and good hydrogel. A polymer compound having such properties can be applied to various applications, and can be used as, for example, hydrogels, medical devices, ophthalmic lenses, DDS devices, etc.
• the compound polymerizable with the polymerizable carbosiloxane dendron of general formula (1) is not particularly limited as long as it can be a monomer component as is commonly known, but for example, hydrophilic compounds are preferably used.
• the hydrophilic compound copolymerizable with the polymerizable carbosiloxane dendron of general formula (1) is not particularly limited as long as it can be a hydrophilic monomer component as is commonly known, but examples include (meth)acrylic monomers such as N,N-dimethylacrylamide, 2-hydroxyethyl methacrylate, (meth)acrylic acid, polyethylene glycol monomethacrylate, and glycerol methacrylate, and vinyl monomers such as N-vinylpyrrolidone, N-vinyl-N-methylacetamide, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide, and N-vinylformamide, and these can be used alone or in combination of two or more.
• (meth)acrylic monomers such as N,N-dimethylacrylamide, 2-hydroxyethyl methacrylate, (meth)acrylic acid, polyethylene glycol monomethacrylate, and gly
• the amount of the hydrophilic compound copolymerizable with the polymerizable carbosiloxane dendron of general formula (1) is not particularly limited, but is, for example, 25 to 99.9 mass % relative to the total amount of the polymer compound, preferably 30 to 99.7 mass %, and more preferably 35 to 99.5 mass %.
• the amount of the hydrophobic compound copolymerizable with the polymerizable carbosiloxane dendron of general formula (1) is not particularly limited, but is, for example, 0 to 30 mass % and preferably 0 to 20 mass % relative to the total amount of the polymer compound. If the amount of the hydrophobic compound copolymerizable with the polymerizable carbosiloxane dendron of general formula (1) exceeds 30 mass %, the strength, shape stability, flexibility, etc. of the resulting polymer compound may decrease.
• crosslinking compounds such as (meth)acrylate-based crosslinking compounds such as ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, and pentaerythritol tri(meth)acrylate, and vinyl-based crosslinking compounds such as allyl methacrylate, diallyl maleate, diallyl fumarate, diallyl succinate, diallyl phthalate, triallyl cyanurate, triallyl isocyanurate, diethylene glycol bisallyl carbonate, triallyl phosphate, triallyl trimellitate, diallyl ether, N,N-diallyl melamine, and divinylbenzene, as constituent
• (meth)acrylate-based crosslinking compounds such as ethylene glycol di(meth)acryl
• the amount of the crosslinkable compound is not particularly limited, but is, for example, 0.01 to 10% by mass, and preferably 0.05 to 3% by mass, based on the total amount of the polymer compound. If the amount of the crosslinkable compound exceeds 10% by mass, the flexibility of the resulting polymer compound may decrease.
• the polymer compound of one embodiment of the present invention can be produced by combining steps known to those skilled in the art.
• the production method is not particularly limited, but can include, for example, the following steps (1) to (3).
• (1) a step of adding a polymerization initiator to a mixture of monomer compounds such as the polymerizable carbosiloxane dendron of general formula (1), a hydrophilic compound copolymerizable with the polymerizable carbosiloxane dendron of general formula (1), a hydrophobic compound copolymerizable with the polymerizable carbosiloxane dendron of general formula (1), and a crosslinking compound, which are constituent components, and stirring and dissolving the mixture to obtain a monomer mixture;
• (2) A step of pouring the obtained monomer mixture into a desired mold and obtaining a copolymer by a copolymerization reaction;
• (3) A process in which the copolymer is cooled, peeled off from the mold, cut and polished as necessary,
• peroxide-based polymerization initiators such as lauroyl peroxide, cumene hydroperoxide, and benzoyl peroxide, which are common radical polymerization initiators, and azo-based polymerization initiators such as azobisdimethylvaleronitrile and azobisisobutyronitrile (AIBN) can be used alone or in combination of two or more.
• the amount of polymerization initiator to be added is not particularly limited as long as it is an amount sufficient to promote the copolymerization reaction of the monomers, and for example, 10 to 7000 ppm based on the total mass of the monomers of the polymerization components is preferable.
• the process for obtaining a copolymer can be carried out by placing the monomer mixture in a metal, glass, plastic or other mold, sealing it, and raising the temperature in a thermostatic chamber or the like, either stepwise or continuously, to a range of 25°C to 120°C, and completing the polymerization in 5 to 120 hours.
• a thermostatic chamber or the like for polymerization, ultraviolet rays, electron beams, gamma rays, etc. can be used.
• solution polymerization can be applied by adding water or an organic solvent to the monomer mixture.
• the process for obtaining a polymer compound involves cooling to room temperature after polymerization is complete, peeling the resulting polymer from the mold, cutting and polishing it as necessary, and then hydrating and swelling it to form a hydrogel.
• the liquid (swelling liquid) used include water, physiological saline, and isotonic buffer solutions.
• the swelling liquid is heated to 60-100°C and the material is immersed for a certain period of time to cause it to swell. It is also preferable to remove unpolymerized monomers contained in the polymer during the swelling process.
• Example 1 Synthesis of polymerizable carbosiloxane dendron (1-1) 1-1. Overview According to the following synthesis scheme (I), a polymerizable carbosiloxane dendron (1-1) having a dicarbonyl residue in the linker was synthesized.
• the NMR spectrum of the resulting polymerizable carbosiloxane dendron (1-1) was as follows: 1H -NMR (500MHz, CDCl3 ) ⁇ ppm: 6.13 (s, 1H), 5.60 (s, 1H), 4.34 (s, 4H), 3.72 (t, 12H), 3.54 (t, 12H), 3.44 (t, 12H), 3.19 (q, 2H), 2.69 (t, 2H), 2.
• Example 2 Synthesis of polymerizable carbosiloxane dendron (1-2) 2-1. Overview According to the following synthesis scheme (II), a polymerizable carbosiloxane dendron (1-2) having a dicarbonyl residue in the linker was synthesized.
• Example 3 Formation of Hydrogel 1 According to Table 1, 50 parts by mass of polymerizable carbosiloxane dendron (1-1), 49 parts by mass of hydroxyethyl methacrylate, 1 part by mass of ethylene glycol dimethacrylate, and 3000 ppm of AIBN were weighed out and stirred at room temperature for 30 minutes while replacing with nitrogen. After stirring, the monomer mixture was placed in a mold and heated to a temperature range of 25 to 120°C over 24 hours to obtain a polymer. The polymer removed from the mold was swollen in a 50% ethanol solution at about 70°C, and then immersed in physiological saline at 25°C for about 1 hour to obtain Hydrogel 1.
• Example 4 Formation of Hydrogel 2 According to Table 1, 65 parts by mass of polymerizable carbosiloxane dendron (1-1), 13 parts by mass of dimethylacrylamide, 13 parts by mass of N-vinylpyrrolidone, 3.55 parts by mass of 2-hydroxybutyl methacrylate, 5 parts by mass of lauryl acrylate, 0.45 parts by mass of ethylene glycol dimethacrylate, and 3000 ppm of AIBN were weighed out and stirred for 30 minutes at room temperature while replacing with nitrogen. After stirring, the monomer mixture was placed in a mold and heated to a temperature of 25 to 120°C over 24 hours to obtain a polymer. The polymer removed from the mold was swollen in a 50% ethanol solution at about 70°C, and then immersed in physiological saline at 25°C for about 1 hour to obtain hydrogel 2.
• Example 5 Formation of Hydrogel 3 According to Table 1, 65 parts by mass of polymerizable carbosiloxane dendron (1-2), 13 parts by mass of dimethylacrylamide, 13 parts by mass of N-vinylpyrrolidone, 3.55 parts by mass of 2-hydroxybutyl methacrylate, 5 parts by mass of lauryl acrylate, 0.45 parts by mass of ethylene glycol dimethacrylate, and 3000 ppm of AIBN were weighed out and stirred for 30 minutes at room temperature while replacing with nitrogen. After stirring, the monomer mixture was placed in a mold and heated to a temperature of 25 to 120°C over 24 hours to obtain a polymer. The polymer removed from the mold was swelled in a 50% ethanol solution at about 70°C, and then immersed in physiological saline at 25°C for about 1 hour to obtain Hydrogel 3.
• Example 7 Synthesis of polymerizable carbosiloxane dendron (1-5) 7-1. Overview According to the following synthesis scheme (IV), a polymerizable carbosiloxane dendron (1-5) having a dicarbonyl residue in the linker was synthesized.
• reaction solution was stirred at 60° C. for an additional 4 hours.
• the reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography to obtain 6.33 g of polymerizable carbosiloxane dendron (1-5) as a colorless, transparent liquid.
• Example 8 Formation of Hydrogel 4 According to Table 1, 50 parts by weight of polymerizable carbosiloxane dendron (1-3), 49 parts by weight of hydroxyethyl methacrylate, 1 part by weight of ethylene glycol dimethacrylate, and 3000 ppm of AIBN were weighed out and stirred at room temperature for 30 minutes while replacing with nitrogen. After stirring, the monomer mixture was placed in a mold and heated to a temperature of 25 to 120°C over 24 hours to obtain a polymer. The polymer removed from the mold was swollen in a 50% ethanol solution at about 70°C, and then immersed in physiological saline at 25°C for about 1 hour to obtain Hydrogel 4.
• Example 9 Formation of Hydrogel 5 According to Table 1, 65 parts by weight of polymerizable carbosiloxane dendron (1-3), 13 parts by weight of dimethylacrylamide, 13 parts by weight of N-vinylpyrrolidone, 3.55 parts by weight of 2-hydroxybutyl methacrylate, 5 parts by weight of lauryl acrylate, 0.45 parts by weight of ethylene glycol dimethacrylate, and 3000 ppm of AIBN were weighed out and stirred at room temperature for 30 minutes while replacing with nitrogen. After stirring, the monomer mixture was placed in a mold and heated to a temperature of 25 to 120°C over 24 hours to obtain a polymer. The polymer removed from the mold was swelled in a 50% ethanol solution at about 70°C, and then immersed in physiological saline at 25°C for about 1 hour to obtain Hydrogel 5.
• Table 1 65 parts by weight of polymerizable carbosiloxane dendron (1-3), 13 parts by weight of dimethylacrylamide, 13 parts by weight of N
• Example 10 Formation of Hydrogel 6 According to Table 1, 62.81 parts by mass of polymerizable carbosiloxane dendron (1-3), 21.56 parts by mass of dimethylacrylamide, 13.74 parts by mass of N-vinylpyrrolidone, 1.26 parts by mass of methacrylic acid, 0.63 parts by mass of triethylene glycol dimethacrylate, and 7000 ppm of AIBN were weighed out and stirred at room temperature for 30 minutes while replacing with nitrogen. After stirring, the monomer mixture was placed in a mold and heated to a temperature of 25 to 120°C over 24 hours to obtain a polymer. The polymer removed from the mold was swelled in a 50% ethanol solution at about 70°C, and then immersed in physiological saline at 25°C for about 1 hour to obtain Hydrogel 6.
• Example 11 Formation of Hydrogel 7 According to Table 1, 62.81 parts by weight of polymerizable carbosiloxane dendron (1-5), 21.56 parts by weight of dimethylacrylamide, 13.74 parts by weight of N-vinylpyrrolidone, 1.26 parts by weight of methacrylic acid, 0.63 parts by weight of triethylene glycol dimethacrylate, and 7000 ppm of AIBN were weighed out and stirred at room temperature for 30 minutes while replacing with nitrogen. After stirring, the monomer mixture was placed in a mold and heated to a temperature of 25 to 120°C over 24 hours to obtain a polymer. The polymer removed from the mold was swelled in a 50% ethanol solution at about 70°C, and then immersed in physiological saline at 25°C for about 1 hour to obtain Hydrogel 7.
• the polymerizable carbosiloxane dendron according to one embodiment of the present invention and the polymer compound containing the same as a constituent component can be used as a raw material for hydrogels, medical devices, ophthalmic lenses, DDS devices, and the like.

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