JP2009263357A - Acrylic compound and vinyl compound - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an acrylic compound having a phosphorylcholine-like group excellent in hydrolysis resistance, a method for producing the acrylic compound in a simple synthetic method, a polymer of the acrylic compound, a vinyl compound and a method for producing the vinyl compound in a simple synthetic method, a surface modifier and a method for modifying the surface. <P>SOLUTION: The acrylic compound is sequentially bonded with a functional group represented by general formula (wherein R<SP>1</SP>, R<SP>2</SP>and R<SP>3</SP>independently represent each a 1C-6C alkyl group; m represents an integer of 2-6), an ester or amide bond, a spacer and an ester or amide bond. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to an acrylic compound, a method for producing an acrylic compound, an acrylic polymer, a vinyl compound, a method for producing a vinyl compound, a surface modifier, and a surface modification method.

  Conventionally, a polymer having a phosphorylcholine group is known as a biocompatible polymer, and biocompatible materials obtained by coating various resin materials with such a polymer are known.

  Patent Document 1 discloses a powder for cosmetics obtained by coating powder with a polymer obtained by polymerizing 2-methacryloyloxyethyl phosphorylcholine as one of the monomers.

  Patent Document 2 discloses a copolymer based on a monomer having a phosphorylcholine-like group in the side chain on the surface of a substrate and a monomer having a group capable of binding to heparin or a heparin derivative, heparin. Or the medical material in which the coating layer comprised from a heparin derivative is formed is disclosed.

  Further, Patent Document 3 includes a phosphorous choline-like group at least on the surface, and an amount P of phosphorus element derived from the phosphorylcholine-like group and an amount C of carbon element in a spectrum measured by X-ray photoelectron spectroscopy of the surface. A separation material having a ratio (P / C) of 0.002 to 0.3 is disclosed.

  On the other hand, Patent Document 4 discloses a copolymer of 2-methacryloyloxyethyl phosphorylcholine (MPC) and a methacrylic acid ester. Patent Document 5 discloses a method for producing a phosphorylcholine group-containing polymer.

  MPC is obtained, for example, by reacting 2-chloro-1,3,2-dioxaphosphorane-2-oxide with 2-hydroxyethyl methacrylate and then reacting with trimethylamine. However, the acrylic compound having a phosphorylcholine-like group thus obtained has a complicated synthesis method and insufficient hydrolysis resistance.

JP 7-118123 A JP 2000-279512 A JP 2002-98676 A JP-A-9-3132 JP-A-10-298240

  In view of the problems of the above-described conventional techniques, the present invention provides an acrylic compound having a phosphorylcholine-like group that has a simple synthesis method and is excellent in hydrolysis resistance, a method for producing the acrylic compound, and a polymerization of the acrylic compound. It aims at providing the acrylic polymer obtained by doing.

  Another object of the present invention is to provide a vinyl compound having a phosphorylcholine-like group that has a simple synthesis method and is excellent in hydrolysis resistance, and a method for producing the vinyl compound.

  Furthermore, an object of the present invention is to provide a surface modifier containing the acrylic compound, the acrylic polymer or the vinyl compound, and a surface modifying method using the surface modifier.

  The invention according to claim 1 is an acrylic compound having a general formula

(In the formula, R ¹ , R ² and R ³ are each independently an alkyl group having 1 to 6 carbon atoms, and m is an integer of 2 to 6)
A functional group represented by the formula: ester bond or amide bond, spacer, ester bond or amide bond, and general formula

(In the formula, R ⁴ is a hydrogen atom or an alkyl group having 1 to 18 carbon atoms.)
Are sequentially bonded to each other.

  The invention according to claim 2 is the acrylic compound according to claim 1, wherein

(Wherein X is an oxy group or imino group, Y is an alkylene group having 1 to 18 carbon atoms, a polyoxyalkylene group or arylene group having 1 to 18 units, and Z is Ester bond or amide bond.)
It is represented by.

  Invention of Claim 3 is a manufacturing method of the acryl-type compound of Claim 1 or 2, Comprising: It has the process of synthesize | combining the compound which has a carboxyl group and a phosphorylcholine group by oxidizing glycerophosphorylcholine. Features.

  The invention according to claim 4 is an acrylic polymer, characterized in that it is a homopolymer or copolymer of the acrylic compound according to claim 1 or 2.

  The invention according to claim 5 is a vinyl compound having a general formula

(In the formula, R ¹ , R ² and R ³ are each independently an alkyl group having 1 to 6 carbon atoms, and m is an integer of 2 to 6)
Functional group represented by the formula, ester bond or amide bond, spacer and general formula

(In the formula, R ⁴ is a hydrogen atom or an alkyl group having 1 to 18 carbon atoms.)
Are sequentially bonded to each other.

  The invention according to claim 6 is the vinyl compound according to claim 5, wherein

(In the formula, X is an alkylene group having 1 to 18 carbon atoms, a polyoxyalkylene group or an arylene group having 1 to 18 units, and Y is an ester bond or an amide bond.)
It is represented by.

  Invention of Claim 7 is a manufacturing method of the vinyl type compound of Claim 5 or 6, Comprising: It has the process of synthesize | combining the compound which has a carboxyl group and a phosphorylcholine group by oxidizing glycerophosphorylcholine. Features.

  The invention according to claim 8 is the surface modifier, wherein the acrylic compound according to claim 1 or 2, the acrylic polymer according to claim 4, or the vinyl compound according to claim 5 or 6. It is characterized by containing.

  The invention according to claim 9 is characterized in that, in the surface modification method, the surface of the material is modified using the surface modifier according to claim 8.

  According to the present invention, an acrylic compound having a phosphorylcholine-like group having a simple synthesis method and excellent hydrolysis resistance, a method for producing the acrylic compound, and an acrylic polymer obtained by polymerizing the acrylic compound. Coalescence can be provided.

  In addition, according to the present invention, a vinyl compound having a phosphorylcholine-like group with a simple synthesis method and excellent hydrolysis resistance, and a method for producing the vinyl compound can be provided.

  Furthermore, the present invention can provide a surface modifier containing the acrylic compound, the acrylic polymer or the vinyl compound, and a surface modification method using the surface modifier.

1 is a diagram showing a ¹ H NMR spectrum of compound B in Example 1. FIG. 1 is a diagram showing an MS spectrum of compound B in Example 1. FIG. It is a figure which shows the evaluation result of the protein adsorption test 1 of an Example. 4 is a diagram showing a ¹ H NMR spectrum of compound G in Example 3. FIG. 4 is a diagram showing an MS spectrum of compound G in Example 3. FIG. It is a figure which shows the evaluation result of the protein adsorption test 2 of an Example.

  Next, the form for implementing this invention is demonstrated with drawing.

[Acrylic compounds]
The acrylic compound of the present invention has the general formula (1)

^(Wherein, R 1, ^{R 2} and ^{R 3} are each independently an alkyl group having 1 to 6 carbon atoms, m is an integer from 2 to 6.)
A phosphorylcholine-like group represented by formula (2): ester bond or amide bond, spacer, ester bond or amide bond

(In the formula, R ⁴ is a hydrogen atom or an alkyl group having 1 to 18 carbon atoms.)
Are sequentially bonded. Thereby, the acrylic compound which is excellent in hydrolysis resistance is obtained. In addition, these acrylic compounds can modify the surface of the material regardless of purification or non-purification, and effects such as suppression of protein adsorption can be obtained.

  Further, the acrylic compound of the present invention has a general formula

(In the formula, X is an oxy group or imino group, Y is an alkylene group having 1 to 18 carbon atoms, a polyoxyalkylene group or arylene group having 1 to 18 units, and Z is an ester bond) Or an amide bond.)
The compound represented by these is preferable. At this time, examples of the polyoxyalkylene group include a polyoxyethylene group and a polyoxypropylene group. Examples of the arylene group include a phenylene group, a hydroxyphenylene group, and a phenylenemethylene group. Further, the alkylene group, polyoxyalkylene group and arylene group may be substituted with other hydrocarbon functional groups.

  The acrylic compound of the present invention includes a compound having a phosphorylcholine-like group and a carboxyl group represented by the general formula (1), a functional group represented by the general formula (2), an ester bond or an amide bond, a spacer, and a hydroxyl group. Alternatively, it can be obtained by condensing a compound in which amino groups are sequentially bonded.

  The acrylic compound of the present invention includes a compound having a phosphorylcholine-like group represented by the general formula (1) and a hydroxyl group or an amino group, and a functional group, an ester bond or an amide bond represented by the general formula (2). , And a compound in which a spacer and a carboxyl group are sequentially bonded to each other.

  At this time, for example, a compound having a phosphorylcholine group and a carboxyl group can be obtained by oxidizing glycerophosphorylcholine using periodic acid and ruthenium trichloride. Moreover, the compound which has a phosphorylcholine group, a hydroxyl group, or an amino group is obtained by condensing the compound which has a phosphorylcholine group and a carboxyl group with diol or diamine.

  The acrylic compound of the present invention can be used as a surface modifier, and is modified by introducing a desired amount of phosphorylcholine-like groups on the surface of the material. At this time, the materials whose surface can be modified include polyethylene, polypropylene, polystyrene, polyvinyl chloride, nylon, polyurethane, polyurea, poly (meth) acrylic acid, poly (meth) acrylate, polyester, poly Examples include acrylonitrile, polyacrylamide, polyvinyl acetate, polycarbonate, polysulfone, polyvinyl alcohol, cellulose, cellulose acetate, silicone resin, glass, ceramic, metal, stainless steel, and the like.

  When modifying the surface of the material using the acrylic compound of the present invention, the surface of the material is treated by plasma treatment, ozone treatment, etc., and then a solution or dispersion of the acrylic compound is applied to the surface of the material. Thus, it is preferable to polymerize and graft the acrylic compound. At this time, vacuum drying, heat treatment, or the like may be performed as necessary. The solvent used for the acrylic compound solution or dispersion is not particularly limited. The concentration of the acrylic compound in the solution or dispersion is preferably 0.01 to 30% by weight, more preferably 0.1 to 20% by weight. When this concentration is less than 0.01% by weight, the amount of the acrylic compound formed on the surface of the material becomes insufficient, and performance may not be exhibited. On the other hand, when the concentration exceeds 30% by weight, the workability when applying the solution or dispersion of the acrylic compound is deteriorated, and the uniformity of the coating film may be lowered. Examples of the coating method include known methods such as a dipping method, a spray method, a roller coating method, and a spin coating method.

  The acrylic polymer of the present invention can be obtained by radical polymerization of the acrylic compound of the present invention in a solvent in the presence of a polymerization initiator. The solvent is not particularly limited as long as the monomer is soluble, but includes water, methanol, ethanol, propanol, t-butanol, benzene, toluene, dimethylformamide, tetrahydrofuran, chloroform, and the like. Also good.

  The polymerization initiator is not particularly limited, and examples thereof include benzoyl peroxide, t-butylperoxy-2-ethylhexanoate, succinyl peroxide, glutarperoxide, succinylperoxyglutarate, and t-butylperoxide. Organic peroxides such as oxymalate, t-butyl peroxypivalate, di-2-ethoxyethyl peroxycarbonate, 3-hydroxy-1,1-dimethylbutyl peroxypivalate, azobisisobutyronitrile, Dimethyl-2,2-azobisisobutyrate, 1-((1-cyano-1-methylethyl) azo) formamide, 2,2-azobis (2-methyl-N-phenylpropionamidin) dihydrochloride, 2,2-azobis (2-methyl-N- (2-hydroxyethyl) Lopionamide), 2,2-azobis (2-methylpropionamide) dihydrate, 4,4-azobis (4-cyanopentanoic acid), 2,2-azobis (2- (hydroxymethyl) propionitrile) and the like A compound etc. are mentioned and you may use 2 or more types together. The polymerization initiator is preferably added in an amount of 0.001 to 10% by weight, more preferably 0.01 to 5% by weight, in the monomer solution.

  In addition, you may copolymerize the acryl-type compound of this invention with another monomer. Although it does not specifically limit as another monomer, A monofunctional monomer is preferable, for example, (meth) acrylic acid, (meth) acrylic acid methyl, (meth) acrylic acid ethyl, (meth) acrylic acid propyl, (meth) acrylic (Meth) acrylate esters such as butyl acid, hexyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate; 2-hydroxyethyl (meth) acrylate, 2-hydroxy (meth) acrylate Hydroxyalkyl (meth) acrylates such as propyl; (meth) acrylic amides; styrene monomers such as styrene, methylstyrene, and substituted styrene; vinyl ethers such as ethyl vinyl ether and butyl vinyl ether; N-vinyl pyrrolidone; vinyl chloride, vinylidene chloride , Ethylene, propylene, iso Unsaturated hydrocarbon monomers or substituted unsaturated hydrocarbon monomers such as tyrene; acrylonitrile; glyco-2-hydroxyethyl monomethacrylate (GEMA); oligoethylene glycol monomethacrylate; polyethylene glycol monomethacrylate, etc., two or more You may use together.

  At this time, the ratio of the acrylic compound of the present invention to the total amount of monomers is preferably 5 mol% or more, and more preferably 20 mol% or more. Thereby, characteristics of phosphorylcholine-like groups such as biocompatibility and moisture retention can be sufficiently expressed.

  The monomer concentration in the solvent is preferably 0.01 to 2 mol / l. By setting the monomer concentration to 0.01 mol / l or more, initiator efficiency can be increased, and by setting the concentration to 2 mol / l or less, polymerization abnormality and gelation can be suppressed.

  The polymerization temperature is usually 5 to 100 ° C. By setting the polymerization temperature to 5 ° C. or higher, the polymerization reaction can be rapidly advanced, and by setting the polymerization temperature to 100 ° C. or lower, the decomposition of the phosphorylcholine-like group due to high temperature can be suppressed. The polymerization time is usually 10 minutes to 24 hours, preferably 30 minutes to 12 hours.

  The acrylic polymer of the present invention can be used as a surface modifier, and is modified by introducing a desired amount of phosphorylcholine-like groups on the surface of the material. At this time, the materials whose surface can be modified include polyethylene, polypropylene, polystyrene, polyvinyl chloride, nylon, polyurethane, polyurea, poly (meth) acrylic acid, poly (meth) acrylate, polyester, poly Examples include acrylonitrile, polyacrylamide, polyvinyl acetate, polycarbonate, polysulfone, polyvinyl alcohol, cellulose, cellulose acetate, silicone resin, glass, ceramic, metal, stainless steel, and the like.

  When the surface of a material is modified using the acrylic polymer of the present invention, it is preferable to apply and dry an acrylic polymer solution or dispersion on the surface of the material. At this time, vacuum drying, heat treatment, or the like may be performed as necessary. The solvent used for the acrylic polymer solution or dispersion is not particularly limited. The concentration of the acrylic polymer in the solution or dispersion is preferably 0.01 to 30% by weight, more preferably 0.1 to 20% by weight. When this concentration is less than 0.01% by weight, the amount of the acrylic polymer formed on the surface of the material becomes insufficient, and performance may not be exhibited. On the other hand, if the concentration exceeds 30% by weight, workability when applying the acrylic polymer solution or dispersion may deteriorate, and the uniformity of the coating film may be reduced. Examples of the coating method include known methods such as a dipping method, a spray method, a roller coating method, and a spin coating method.

[Vinyl compounds]
The vinyl compound of the present invention has the general formula (1)

^(Wherein, R 1, ^{R 2} and ^{R 3} are each independently an alkyl group having 1 to 6 carbon atoms, m is an integer from 2 to 6.)
A phosphorylcholine-like group, an ester bond or an amide bond, a spacer, and a general formula (2)

(In the formula, R ⁴ is a hydrogen atom or an alkyl group having 1 to 18 carbon atoms.)
Are sequentially bonded. Thereby, the vinyl type compound excellent in hydrolysis resistance is obtained. These vinyl compounds can modify the surface of the material regardless of purification or non-purification, and can provide effects such as suppression of protein adsorption.

  Further, the vinyl compound of the present invention has a general formula

(In the formula, X is an alkylene group having 1 to 18 carbon atoms, a polyoxyalkylene group or an arylene group having 1 to 18 units, and Y is an ester bond or an amide bond.)
The compound represented by these is preferable. At this time, examples of the polyoxyalkylene group include a polyoxyethylene group and a polyoxypropylene group. Examples of the arylene group include a phenylene group, an oxyphenylene group, and a methylenephenylene group. Further, the alkylene group, polyoxyalkylene group and arylene group may be substituted with other hydrocarbon functional groups.

  The vinyl compound of the present invention comprises a compound having a phosphorylcholine-like group and a carboxyl group represented by the general formula (1), and a functional group and a hydroxyl group or amino group represented by the general formula (2) via a spacer. It is obtained by condensing the bound compounds.

  The vinyl compound of the present invention includes a phosphorylcholine-like group represented by the general formula (1) and a hydroxyl group or amino group, and a functional group and a carboxyl group represented by the general formula (2) as spacers. It can be obtained by condensing a compound bonded through the compound.

  At this time, for example, a compound having a phosphorylcholine group and a carboxyl group can be obtained by oxidizing glycerophosphorylcholine using periodic acid and ruthenium trichloride. Moreover, the compound which has a phosphorylcholine group, a hydroxyl group, or an amino group is obtained by condensing the compound which has a phosphorylcholine group and a carboxyl group with diol or diamine.

  The vinyl compound of the present invention can be used as a surface modifier, and is modified by introducing a desired amount of phosphorylcholine-like groups on the surface of the material. At this time, the materials whose surface can be modified include polyethylene, polypropylene, polystyrene, polyvinyl chloride, nylon, polyurethane, polyurea, poly (meth) acrylic acid, poly (meth) acrylate, polyester, poly Examples include acrylonitrile, polyacrylamide, polyvinyl acetate, polycarbonate, polysulfone, polyvinyl alcohol, cellulose, cellulose acetate, silicone resin, glass, ceramic, metal, stainless steel, and the like.

  When modifying the surface of the material using the vinyl compound of the present invention, the surface of the material is treated by plasma treatment, ozone treatment, etc., and then a solution or dispersion of the vinyl compound is applied to the surface of the material. Thus, it is preferable to polymerize and graft the vinyl compound. At this time, vacuum drying, heat treatment, or the like may be performed as necessary. The solvent used for the solution or dispersion of the vinyl compound is not particularly limited. The concentration of the vinyl compound in the solution or dispersion is preferably 0.01 to 30% by weight, more preferably 0.1 to 20% by weight. If this concentration is less than 0.01% by weight, the amount of vinyl compound formed on the surface of the material becomes insufficient, and performance may not be exhibited. On the other hand, if the concentration exceeds 30% by weight, the workability when applying a solution or dispersion of a vinyl compound is deteriorated, and the uniformity of the coating film may be lowered. Examples of the coating method include known methods such as a dipping method, a spray method, a roller coating method, and a spin coating method.

[Example 1]
An aqueous solution of L-α-glycerophosphorylcholine was cooled in an ice-water bath. Next, after adding 4 period equivalent sodium periodate of L-α-glycerophosphorylcholine, a catalytic amount of ruthenium trichloride was added, and the mixture was stirred for 3 hours to be reacted. Next, methanol was added and the mixture was further stirred for 30 minutes, and then the precipitate was removed by filtration. Furthermore, after concentration under reduced pressure, drying under reduced pressure, chemical formula

The compound A represented by these was obtained.

  Next, in DMSO, compound A and 2-hydroxyethyl methacrylate (HEMA) are added and stirred at room temperature to cause reaction.

(Acrylic compound having a phosphorylcholine group with a molecular weight of 354) was obtained (see FIGS. 1 and 2). In addition, the compound B can be used as a surface modifier similarly to the compound G mentioned later.

[Example 2]
After adding 20 times equivalent of ethylenediamine to compound A in methanol solution of compound A, 1.2 times equivalent of triazine type dehydrating condensing agent DMT-MM (manufactured by Kokusan Kagaku Co.) is added at room temperature The reaction was stirred for 3 hours. Next, the precipitate is removed by filtration, concentrated under reduced pressure, and then dried under reduced pressure.

The compound C represented by these was obtained.

  Next, compound C and methacrylic acid chloride are added to DMSO, and the mixture is stirred at room temperature and reacted.

The compound D (acrylic compound which has a phosphorylcholine group) represented by these was obtained. In addition, the compound D can be used as a surface modifier similarly to the compound G mentioned later.

After adding Compound D and butyl methacrylate in a molar ratio of 7: 3 in methanol, 0.05 mol% ammonium peroxodisulfate (NH ₃ ) ₂ S ₂ O ₈ was added to the total amount of monomers. The resultant was added and polymerized at 50 ° C. for 1 hour to obtain Compound E (acrylic polymer having a phosphorylcholine group).

  A 5 wt% methanol solution of Compound E was applied to a polystyrene 96-well plate (Nihon BD). Next, after washing with methanol, it was dried to obtain a surface-treated well plate.

[Comparative Example 1]
After adding 2-hydroxyethyl methacrylate (HEMA) and butyl methacrylate in a ratio of 7: 3 to methanol, 0.05 mol% ammonium peroxodisulfate (NH ₃ ) _{2 with} respect to the total amount of monomers. S ₂ O ₈ was added and polymerized at 50 ° C. for 1 hour to obtain Compound F (acrylic polymer).

  A 5 wt% methanol solution of Compound F was applied to a 96-well polystyrene plate (Nihon BD). Next, after washing with methanol, it was dried to obtain a surface-treated well plate.

[Protein adsorption experiment 1]
The protein was adsorbed to the surface-treated well plate and the untreated well plate of Example 2 and Comparative Example 1, and the amount of adsorbed protein was quantified using the direct BCA method. The proteins used for the evaluation were albumin (Mw = 69000, pI = 4.9), γ-globulin (Mw = 150,000, 5.0 <pI <9.5), lysozyme (Mw = 14000, pI = 11.0). ) (Manufactured by Sigma).

  The experimental method will be specifically described below. First, each protein was mixed with a phosphate buffer (sodium chloride 8 mg / mL, potassium chloride 0.2 mg / mL, sodium monohydrogen phosphate 1.15 mg / mL, diphosphate 2 so that the concentration was 0.1 mg / mL. It was dissolved in potassium hydrogen 0.2 mg / mL, pH = 7.4) to obtain a protein solution. Next, 100 μl of the protein solution was placed in the well of the well plate and allowed to stand at 25 ° C. for 1 hour. Further, the wells were washed 5 times with 200 μl of phosphate buffer, and then 50 μl of PBS and 50 μl of BCA solution were added and allowed to stand at 60 ° C. for 1 hour for color development. Next, the absorbance of light with a wavelength of 562 nm was measured using a plate reader power scan HT (manufactured by Dainippon Sumitomo Pharma Co., Ltd.). In preparing the calibration curve, each protein solution 0, 2, 5, 10, 20, 40 μl was added to the well of the well plate, PBS was added to 50 μl, and 50 μl of the BCA solution was added. Measured the absorbance of light having a wavelength of 562 nm in the same manner as described above. The evaluation results are shown in FIG. From FIG. 3, it can be seen that any of albumin, γ-globulin and lysozyme can suppress the adsorption of the protein to the well plate by surface treatment. Further, it can be seen that the surface-treated well plate of Example 2 can suppress the adsorption of albumin, γ-globulin and lysozyme more than the surface-treated well plate of Comparative Example 1.

[Example 3]
Compound A and 2-fold equivalent carbonyldiimidazole (CDI) of compound A were added to dimethyl sulfoxide (DMSO), and the mixture was stirred and reacted at room temperature. Furthermore, allylamine is dropped and reacted, and the chemical formula

Compound G (vinyl compound having a phosphorylcholine group having a molecular weight of 281) represented by the following formula (see FIGS. 4 and 5) was obtained.

  A 96-well plate made of polystyrene (manufactured by Japan BD) was plasma-treated in an argon atmosphere and then reacted with oxygen gas. Next, it was immersed in a 5% by weight methanol solution of Compound G, washed with methanol, and then dried to obtain a surface-treated well plate.

[Protein adsorption experiment 2]
The amount of protein adsorbed was quantified in the same manner as in protein adsorption experiment 1 except that the surface-treated well plate of Example 3 was used instead of the surface-treated well plate of Example 2 and Comparative Example 1. The evaluation results are shown in FIG. From FIG. 6, it can be seen that any of albumin, γ-globulin and lysozyme can suppress the adsorption of protein to the well plate by surface treatment.

  The material modified by the surface modifier of the present invention is a material excellent in biocompatibility and hydrophilicity. Such materials can be applied to a wide range of uses such as cosmetics, artificial organs, medical materials such as surgical instruments, chromatographic fillers, affinity particles, paints, and the like.

Claims (9)

General formula
(In the formula, R ¹ , R ² and R ³ are each independently an alkyl group having 1 to 6 carbon atoms, and m is an integer of 2 to 6)
A functional group represented by the formula: ester bond or amide bond, spacer, ester bond or amide bond, and general formula
(In the formula, R ⁴ is a hydrogen atom or an alkyl group having 1 to 18 carbon atoms.)
An acrylic compound, wherein functional groups represented by General formula
(Wherein X is an oxy group or imino group, Y is an alkylene group having 1 to 18 carbon atoms, a polyoxyalkylene group or arylene group having 1 to 18 units, and Z is Ester bond or amide bond.)
The acrylic compound according to claim 1, wherein A method for producing the acrylic compound according to claim 1 or 2,
A method for producing an acrylic compound, comprising a step of synthesizing a compound having a carboxyl group and a phosphorylcholine group by oxidizing glycerophosphorylcholine.   An acrylic polymer, wherein the acrylic polymer is a homopolymer or copolymer of the acrylic compound according to claim 1. General formula
(In the formula, R ¹ , R ² and R ³ are each independently an alkyl group having 1 to 6 carbon atoms, and m is an integer of 2 to 6)
Functional group represented by the formula, ester bond or amide bond, spacer and general formula
(In the formula, R ⁴ is a hydrogen atom or an alkyl group having 1 to 18 carbon atoms.)
A vinyl compound characterized in that functional groups represented by General formula
(In the formula, X is an alkylene group having 1 to 18 carbon atoms, a polyoxyalkylene group or an arylene group having 1 to 18 units, and Y is an ester bond or an amide bond.)
The vinyl compound according to claim 5, which is represented by: A method for producing a vinyl compound according to claim 5 or 6,
A method for producing a vinyl compound, comprising a step of synthesizing a compound having a carboxyl group and a phosphorylcholine group by oxidizing glycerophosphorylcholine.   A surface modifier comprising the acrylic compound according to claim 1 or 2, the acrylic polymer according to claim 4, or the vinyl compound according to claim 5 or 6.   A surface modification method comprising modifying a surface of a material using the surface modifier according to claim 8.