Polymer compounds and methods for producing the same, adhesive compositions, and surface modifiers

Abstract

The present invention provides a novel polymer compound having biocompatibility in both its main chain and side chains, a method for producing the same, and an adhesive composition and a surface modifier containing the polymer compound. [Solution] The polymer compound of the present invention has a dopamine moiety in the side chain of polyoxazoline. One embodiment of such a polymer compound is given by the following formula (1) TIFF2026052204000014.tif54170 The polymer compound of the present invention has a structural unit D represented by [formula]. The polymer compound of the present invention comprises a step of reacting dopamine with a precursor.

Description

Technical Field

[0001] The present invention relates to a polymer compound, a method for producing the same, an adhesive composition, and a surface modifier.

Background Art

[0002] Polymer compounds are widely used in various fields. For example, in addition to various functional materials such as adhesives, coating agents, films, packaging materials, dispersants, and binders, they are also applied to medical materials and the food field, and their utility value is extremely high.

[0003] Recently, polymer materials having biocompatibility or biomimetic polymers (biomimetic polymers) have also been actively studied, and various polymer materials with enhanced functionality and performance have been developed through material design mimicking natural phenomena. For example, Non-Patent Document 1 discloses a biomimetic adhesive material in which a dopamine site is introduced into the side chain of a polyacrylate / methacrylate copolymer, and Non-Patent Document 2 discloses a biomimetic adhesive material in which a part of the side chain of polystyrene is substituted with a polyhydroxy-substituted benzene derivative.

Prior Art Documents

Non-Patent Documents

[0004]

Non-Patent Document 1

Non-Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0005] In recent years, there has been a growing demand for biocompatible polymer compounds. However, the biomimetic adhesive materials proposed in the aforementioned Non-Patent Documents 1 and 2, etc., use general-purpose polymers such as polyacrylate / methacrylate or polystyrene as their main chain backbone, and it is difficult to say that the polymer as a whole possesses biocompatibility.

[0006] The present invention has been made in view of the above, and aims to provide a novel polymer compound having biocompatibility in both the main chain and side chains, and a method for producing the same. The present invention also aims to provide a novel adhesive composition and a surface modifier. [Means for solving the problem]

[0007] The inventors of this invention conducted extensive research to achieve the above objective and, as a result, discovered that the above objective can be achieved by introducing a dopamine moiety into the side chain of polyoxazoline, thus completing the present invention.

[0008] In other words, the present invention encompasses, for example, the subject matter described in the following sections. Item 1 A high-molecular-weight compound having a dopamine moiety in the side chain of a polyoxazoline. Section 2 The following formula (1)

[0009] [ka]

[0010] A polymer compound as described in item 1, having a structural unit D represented by the symbol D. Section 3 The polymer compound according to item 2, which is a copolymer having the structural unit D. Section 4 An adhesive composition comprising a polymer compound as described in any one of items 1 to 3. Section 5 A surface modifier comprising a polymer compound as described in any one of items 1 to 3. Section 6 The method for producing a polymer compound according to any one of Items 1 to 3, comprising: a step of reacting dopamine with a precursor, wherein the precursor is a polymer having a structural unit represented by the following formula (2a)

[0011]

Chemical formula

Chemical formula

[0012]

Chemical formula

Advantages of the Invention

[0013] The polymer compound of the present invention has biocompatibility and is suitable as a raw material for various materials such as adhesives and surface modifiers.

Brief Description of the Drawings

[0014] [Figure 1] (a) is a synthesis scheme of the polymer compound produced in Example 1, and (b) is a 1H NMR spectrum of the obtained polymer compound. [Figure 2] (a) is a synthesis scheme of the polymer compound produced in Example 2, and (b) is a 1H NMR spectrum of the obtained polymer compound. [Figure 3] (a) is a synthesis scheme of the polymer compound produced in Example 3, and (b) is a 1H NMR spectrum of the obtained polymer compound. [Figure 4] (a) is a synthesis scheme of the polymer compound produced in Example 4, and (b) is a 1H NMR spectrum of the obtained polymer compound. [Figure 5] It is a schematic diagram explaining the evaluation method of the adhesion performance of the polymer compound carried out in Test Example 1-1. [Figure 6]This is a schematic diagram illustrating the procedure for surface modification using a surface modifier containing a polymer compound, as performed in Test Example 2-1. [Modes for carrying out the invention]

[0015] Embodiments of the present invention will be described in detail below. In this specification, the expressions "containing" and "including" include the concepts of "containing," "including," "substantially consisting of," and "consisting only of."

[0016] 1. Polymer compounds The polymeric compound of the present invention has a dopamine moiety in the side chain of the polyoxazoline. Both the polyoxazoline and the dopamine moiety are biocompatible. In other words, both the main chain and the side chain of the polymeric compound of the present invention are biocompatible (biocompatible). Therefore, the polymeric compound of the present invention is particularly suitable for application in the biomedical field (for example, medical adhesives).

[0017] In particular, the polymer compounds of the present invention have dopamine moieties in their side chains, and therefore possess the property of forming crosslinks between molecules through oxidative polymerization. Due to this property, the polymer compounds of the present invention can exhibit adhesive function. Furthermore, since both the main chain and side chains of the polymer compounds of the present invention are biocompatible (biocompatible), it is also possible to impart biocompatibility to the surfaces of various materials.

[0018] The polymeric compounds of the present invention are not particularly limited in type, as long as they have a dopamine moiety in the side chain of polyoxazoline. Hereinafter, the polymeric compounds of the present invention having a dopamine moiety in the side chain of polyoxazoline will be referred to as "polymeric compound A".

[0019] One embodiment of polymer compound A is a polymer having a structural unit in which a dopamine moiety is introduced into the side chain of a polyoxazoline. The dopamine moiety refers to a moiety derived from dopamine or its derivatives.

[0020] A more specific example of polymer compound A is a polymer having a structural unit represented by the following formula (1) (denoted as "structural unit D"). For clarification, the term "structural unit" refers to a repeating unit within the polymer.

[0021] [ka]

[0022] The aforementioned structural unit D is a structural unit in which the main chain is oxazoline, and the nitrogen atom of dopamine is bonded to the carbonyl carbon (-NC(=O)-) of the oxazoline.

[0023] Polymer compound A may consist only of the structural unit D, or it may have structural units other than the structural unit D. That is, polymer compound A may be a copolymer having the structural unit D. In other words, polymer compound A may be a homopolymer consisting only of the structural unit D, or it may be a copolymer having the structural unit D.

[0024] When polymer compound A is a copolymer, structural units other than structural unit D are denoted as structural unit F. Such structural unit F can be, for example, a structural unit represented by the following formula (1a), taking into consideration the biocompatibility of polymer compound A.

[0025] [ka]

[0026] Here, R in formula (1a) can be any of the various monovalent groups, for example, a hydrocarbon group which may have substituents. The number of carbon atoms in the hydrocarbon group can be, for example, 1 or more and 10 or less, preferably 8 or less, more preferably 6 or less, and even more preferably 4 or less. In the hydrocarbon group which may have substituents, examples of substituents include halogen atoms, carboxyl groups, carbonyl groups, sulfonyl groups, sulfone groups, cyano groups, and the like.

[0027] Examples of hydrocarbon groups that may have substituents include alkyl groups, alkenyl groups, alkynyl groups, and aryl groups, with alkyl groups being preferred.

[0028] In formula (1a), specific examples of R include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, t-butyl group, and the like.

[0029] When polymer compound A has structural unit D and structural unit F, the content ratio of each structural unit is not particularly limited. For example, in such a case, polymer compound A preferably contains 1 mol% or more of structural unit D, preferably 2 mol% or more, more preferably 3 mol% or more, and preferably 90 mol% or less. It is more preferable that the content be 70 mol% or less, even more preferable that it be 60 mol% or less, and particularly preferable that it be 50 mol% or less. In these cases, the remainder can be structural unit F.

[0030] If polymer compound A is a copolymer having structural unit D and structural unit F, polymer compound A may consist only of structural unit D and structural unit F, or it may have other structural units as long as the effects of the present invention are not hindered. If polymer compound A contains structural units other than structural unit D and structural unit F, the content of such units is preferably 10% by mass or less, more preferably 5% by mass or less, and even more preferably 1% by mass or less, relative to the total amount of polymer compound A.

[0031] Other structural units besides structural units D and F include structural units derived from raw materials used in the production method of polymer compound A, such as structural units contained in the precursor described later.

[0032] When the polymer compound of the present invention is a copolymer, it can form various polymers such as block copolymers, random copolymers, and graph copolymers, and among these, block copolymers are preferred.

[0033] The number-average molecular weight of the polymer compound of the present invention is not particularly limited and can be adjusted to a desired range depending on the application. For example, the number-average molecular weight (Mn) of the polymer compound of the present invention is preferably 2000 or more, more preferably 3000 or more, even more preferably 4000 or more, preferably 500000 or less, more preferably 300000 or less, even more preferably 100000 or less, and particularly preferably 50000 or less. In this invention, the number-average molecular weight refers to the polystyrene-equivalent number-average molecular weight measured by gel permeation chromatography (GPC).

[0034] Since both the main chain and side chains of the present invention consist solely of biocompatible components, the polymer compound is suitable for application in the biomedical field, and is particularly suitable for application in medical adhesives.

[0035] 2. Method for producing polymer compounds The method for producing polymer compound A is not particularly limited, and for example, a wide range of known methods for producing polymer compounds can be employed. In particular, the method for producing polymer compound A is preferably one that includes a step of reacting dopamine with a precursor, as this makes it easy to produce polymer compound A. Hereinafter, this step will be referred to as "step S".

[0036] In step S, the precursor may be a polymer having a structural unit represented by the following formula (2a), or a polymer having a structural unit represented by the following formula (2b).

[0037] [ka]

[0038] [ka]

[0039] The method for producing the polymer having the structural units represented by formulas (2a) and (2b) (i.e., the precursor) is not particularly limited and can be produced by known methods, for example. For example, see Non-Patent Document 3 below. [Non-patent document 3] M. Swager et al. J. Am. Chem. Soc. 2019, 141, 32, 12498-12501 A polymer having the structural unit represented by formula (2a) or formula (2b) can be produced by the method described above. Alternatively, polymers having the structural units represented by formulas (2a) and (2b) may be obtained from commercially available products or the like.

[0040] The precursor may have structural units other than the structural unit represented by formula (2a) or formula (2b). Examples of other structural units include the aforementioned structural unit F, for example, the structural unit represented by formula (1a).

[0041] The precursor preferably contains 1 mol% or more of the structural unit represented by formula (2a) or formula (2b), more preferably 2 mol% or more, more preferably 3 mol% or more, more preferably 90 mol% or less, more preferably 70 mol% or less, even more preferably 60 mol% or less, and particularly preferably 50 mol% or less.

[0042] From the viewpoint of significantly improving adhesive performance, the precursor preferably contains 1 to 30 mol%, more preferably 1 to 20 mol%, and even more preferably 1 to 10 mol% of the structural unit represented by formula (2a) or formula (2b).

[0043] The precursor may also have structural units other than the structural unit represented by formula (2a) or formula (2b) and the structural unit represented by formula (1a). The content of such other structural units is preferably 10% by mass or less, more preferably 5% by mass or less, and even more preferably 1% by mass or less, based on the total amount of the precursor.

[0044] The number-average molecular weight of the precursor is not particularly limited and can be appropriately selected according to the molecular weight of the target polymer compound A.

[0045] In step S, dopamine is reacted with the precursor. Dopamine can be obtained, for example, from a commercially available product. Dopamine may also be, for example, a hydrochloride salt.

[0046] In step S, the method of reacting dopamine with the precursor is not particularly limited; for example, the reaction can be carried out by mixing the precursor and dopamine.

[0047] In the reaction of step S, solvents, bases, etc., can be used as needed. The type of solvent is not particularly limited and may include, for example, formamides such as N,N-dimethylformamide and N,N-dimethylacetamide; pyrrolidones such as 2-pyrrolidone and N-methylpyrrolidone; dimethyl sulfoxides; aliphatic hydrocarbons such as hexane and heptane; alicyclic hydrocarbons such as cyclohexane; aromatic hydrocarbons such as benzene, toluene, and xylene; acetone and methyl ethyl Examples include ketone compounds such as ketones, and ester compounds such as vinyl acetate.

[0048] Examples of bases include various amine compounds, with N,N-diisopropylethylamine being a specific example.

[0049] In step S, the reaction temperature between dopamine and the precursor is, for example, 10 to 100°C, preferably 20 to 50°C. The reaction time can be appropriately set according to the reaction temperature, the amount of raw materials used, etc., for example, 1 to 24 hours.

[0050] The reaction in step S causes a nucleophilic reaction of dopamine, in which the nitrogen atom of dopamine bonds to the carbonyl carbon of the precursor. This yields a product containing the target polymer compound A.

[0051] The product obtained in step S can be purified as needed. This increases the purity of polymer compound A in the product. The dopamine introduction rate in step S is not particularly limited, and is, for example, 80-99%. The dopamine introduction rate can be controlled by adjusting the amount of dopamine and the precursor used in step S, as well as the reaction conditions.

[0052] 3. Uses of polymer compounds The polymer compounds of the present invention can be used, for example, as raw materials for adhesive compositions. Such adhesive compositions, containing the polymer compounds of the present invention, are particularly suitable as medical adhesives. In particular, the polymer compounds of the present invention contained in the adhesive compositions have dopamine moieties in their side chains and, as described above, are capable of crosslinking, thus exhibiting excellent adhesive performance.

[0053] For example, the adhesive composition can easily bond adherends to each other by a heat-pressure bonding process. Specifically, a solution (e.g., an aqueous solution) of the adhesive composition dissolved in the adherends is applied or cast to form a film, the other adherend is placed on top of this film to form a laminate, and the laminate is then heat-pressed. The conditions for the heat-pressure bonding process are not particularly limited; for example, the temperature may be 10 to 150°C, preferably 20 to 140°C, and the pressure may be normal pressure (atmospheric pressure atmosphere). If pressurized, the conditions may be the same as those for known pressurized bonding. When the film is heat-pressed, the crosslinking reaction (oxidative polymerization) by the side-chain dopamine of the polymer compounds contained in the adhesive composition proceeds more easily, the film hardens, and excellent adhesive function is exhibited.

[0054] The concentration of the solution in which the adhesive composition is dissolved is not particularly limited and can be set within an appropriate range considering the desired adhesive strength.

[0055] The type of substrate to be bonded by the adhesive composition is not particularly limited, and examples include various resin substrates such as polyethylene, polypropylene, polyester, polyacrylic, polystyrene sulfone, polyethylene terephthalate (PTFE), and polycarbonate, as well as glass substrates and the like.

[0056] The adhesive composition may contain other components in addition to the polymer compound of the present invention. The types of other components are not particularly limited, and for example, components found in known adhesives can be broadly listed. The main component in the adhesive composition may be the polymer compound of the present invention.

[0057] The polymer compound of the present invention can also be used as a raw material for surface modifiers. Since such a surface modifier contains the polymer compound of the present invention, it can, for example, improve the surface of various materials. It can be modified with molecular compounds, and in particular, it can impart biocompatibility to the surfaces of various materials.

[0058] The method for performing surface modification using a surface modifier is not particularly limited. Examples include applying the surface modifier to the material surface to form a film and thereby modifying the material's surface, or immersing the material in a liquid containing the surface modifier to modify the material's surface. Alternatively, a method can be used in which a solution of the surface modifier is cast onto the material surface to form a film, and then the material with the film formed is immersed in a buffer solution. In this method, oxidative polymerization of the side-chain dopamine moieties in the polymer compound occurs in the buffer solution, so a firmly adhering film can be formed on the material surface without the need for heating and pressing. In other words, the surface modifier of the present invention makes it possible to form a film containing a polymer compound under mild conditions.

[0059] If the surface modifier is, for example, a copolymer having the structural unit D and the structural unit represented by formula (1a), the type of modification by the surface modifier can be designed according to the properties of R in formula (1a).

[0060] The surface modifier may contain other components besides the polymer compound of the present invention. The types of other components are not particularly limited, and for example, components included in known surface modifiers can be broadly listed.

[0061] In identifying the inventions contained herein, the components (properties, structures, functions, etc.) described in each embodiment of this disclosure may be combined in any way. That is, this disclosure encompasses all subject matter consisting of any combination of the combinatable components described herein. [Examples]

[0062] The present invention will be described more specifically below with reference to examples, but the present invention is not limited to the embodiments of these examples.

[0063] (Example 1) A polymer compound was produced according to the reaction scheme shown in Figure 1(a). First, a precursor consisting of the structural unit represented by formula (2a) (Mn=12000, Mw / Mn=1.31) was obtained by a conventional method (for example, according to the method described in Non-Patent Document 3 above). This precursor was reacted with 3 molar equivalents of dopamine relative to the precursor and 3 molar equivalents of N,N-diisopropylethylamine (DIPEA) as a base relative to the precursor in DMF at room temperature (25°C) for 16 hours. As a result, dopamine reacted with the side chain of the precursor, and a polymer compound having the structural unit D represented by formula (1) was obtained. The dopamine introduction rate was 98% (i.e., in the product in Figure 1, n=98, m=2).

[0064] As shown in Figure 1(b) 1 From the 1H NMR spectrum (measured in heavy water), it was confirmed that the target polymer compound was obtained by the reaction in Example 1.

[0065] (Example 2) Polymer compound A was produced according to the reaction scheme shown in Figure 2(b). First, a polymer consisting of structural units represented by formula (2b) and formula (1a) (where R is an ethyl group) was prepared as a precursor by a conventional method. In this precursor (Mn=4700), the content of structural units represented by formula (2b) was 39 mol%, and the content of structural units represented by formula (1a) was 61 mol% (i.e., in Figure 2, m=39, n=61). This precursor, along with 3 molar equivalents of dopamine relative to the precursor, and 3 molar equivalents of N,N-diisopropylethylamine as a base relative to the precursor, were heated at room temperature (2 The reaction was carried out in DMF at 5°C for 16 hours. This resulted in the reaction of dopamine with the side chains of the precursor, yielding a copolymer having structural unit D represented by formula (1) and structural unit (R is an ethyl group) represented by formula (1a). The content of structural unit D was 39 mol%, and the content of structural unit (1a) represented by formula (R is an ethyl group) was 61 mol% (i.e., in Figure 2, m=39, n=61).

[0066] As shown in Figure 2(b) 1 From the 1H NMR spectrum (measured in heavy water), it was confirmed that the target polymer compound was obtained by the reaction in Example 2.

[0067] (Example 3) A copolymer was obtained in the same manner as in Example 2, except that the precursor (Mn=4700) was changed to one in which the content of the structural unit represented by formula (2b) was 7 mol% and the content of the structural unit represented by formula (1a) was 93 mol%. The content of the structural unit D was 7 mol%, and the content of the structural unit represented by formula (1a) (R is an ethyl group) was 93 mol% (i.e., in Figure 2, m=7, n=93).

[0068] As shown in Figure 3 1 From the 1H NMR spectrum (measured in heavy water), it was confirmed that the target polymer compound was obtained by the reaction in Example 3.

[0069] (Example 4) A copolymer was obtained in the same manner as in Example 2, except that the precursor (Mn=4700) was changed to one in which the content of the structural unit represented by formula (2b) was 4 mol% and the content of the structural unit represented by formula (1a) was 96 mol%. The content of the structural unit D was 4 mol%, and the content of the structural unit represented by formula (1a) (R is an ethyl group) was 96 mol% (i.e., in Figure 2, m=4, n=96).

[0070] As shown in Figure 4 1 From the 1H NMR spectrum (measured in heavy water), it was confirmed that the target polymer compound was obtained by the reaction in Example 1.

[0071] (Test Example 1-1) The adhesive performance of the polymer compound was evaluated according to the procedure shown in Figure 5. The polymer compound obtained in Example 1 was dissolved in water as a solvent to prepare polymer solutions (adhesive compositions) of three concentrations: 1 mg / mL, 10 mg / mL, and 20 mg / mL. 30 μL of each polymer solution was cast onto a pair of silicon wafers to a size of 1 cm × 1 cm, and then air-dried to create a polymer compound film on each silicon wafer. Next, the films formed on the pair of silicon wafers were overlapped and bonded to form a laminate. When overlapping, the laminates were formed by offsetting them in both directions so that the edges (parts without film) did not overlap. The resulting laminate was placed on a horizontal stand with a load of 50 g applied from one of the silicon wafers, and heat-pressed at 120°C for 1 hour. Spacers were interposed between the horizontal stand and the edges of the laminate to ensure that the pressure from the heat-pressing was evenly distributed across the film. Subsequently, the shear stress was measured by a tensile test of the laminate. For the tensile test, we used a method of gripping the end of the laminate and pulling it in a 180° direction.

[0072] (Results of Test Example 1-1) Table 1 shows the shear stress results measured in Test Example 1-1. Table 1 demonstrates that silicon substrates can be bonded together using polymer solutions of any concentration. Furthermore, visual observation of the material surface after delamination confirmed that cohesive failure, rather than interfacial failure, had occurred.

[0073] [Table 1]

[0074] (Test Example 1-2) In Example 2, the polymer compound obtained was dissolved in water as a solvent to prepare a polymer solution (adhesive composition) with a concentration of 20 mg / mL. Two PTFE substrates that had been pre-plasma treated were prepared as substrates. 30 μL of the polymer solution was cast onto each of the PTFE substrates to a size of 1 cm × 1 cm, and then air-dried to create a polymer compound coating on each PTFE substrate. Next, the coatings formed on the pair of PTFE substrates were overlapped and bonded together to form a laminate. When overlapping, the laminates were formed by offsetting them in both directions so that the ends (parts where no coating was formed) did not overlap. The resulting laminate was placed on a horizontal table with a load of 50 g applied from one of the PTFE substrates, and heat-pressed at 120°C for 1 hour. Spacers were interposed between the horizontal table and the ends of the laminate to ensure that the pressure from the heat-pressing was evenly applied to the coatings. After that, the shear stress was measured by a tensile test of the laminate. For the tensile test, we used a method of gripping the end of the laminate and pulling it in a 180° direction.

[0075] (Test Examples 1-3) Shear stress was measured by a tensile test using the same procedure as in Test Example 1-1, except that the polymer compound was changed to the polymer compounds obtained in Examples 2, 3, and 4, respectively.

[0076] (Test Examples 1-4) Shear stress was measured by a tensile test following the same procedure as in Test Example 1-1, except that the polymer compound was changed to the polymer compound obtained in Example 4, and the method was changed to heat-pressing the laminate on a horizontal table with a 50g load applied from one silicon wafer at 25°C for 1 hour.

[0077] (Test Examples 1-5) Shear stress was measured using the same method as in Test Example 1-2, except that the PTFE substrate was treated with corona treatment instead of plasma treatment.

[0078] (Results of Test Examples 1-2 and 1-5) Table 2 shows the shear stress results measured in Test Examples 1-2 and 1-5. Table 2 demonstrates that PTFE substrates can be bonded together in all cases.

[0079] [Table 2]

[0080] (Results of Test Examples 1-3) Table 3 shows the results of adhesion tests (Test Examples 1-3) using the polymer compounds obtained in Examples 2, 3, and 4, respectively, and the shear stress measured in Test Example 1-1. From Table 3, it can be seen that all polymer compounds provide sufficient shear stress as adhesives, and in particular, when the content of the structural unit D was 7 mol% or 4 mol%, they showed higher adhesion properties than polymer compounds consisting only of the structural unit D. Furthermore, since they showed higher shear stress than polymer compounds consisting of the structural unit represented by formula (1a) (R is an ethyl group) (Poly(EtOx)) and PMMA, it became clear that polymer compounds exhibit superior adhesion properties when they have the structural unit represented by formula (2b). In Examples 1 and 2, the shear stress is lower than that of Poly(EtOx), but the polymer compounds in Examples 1 and 2 are advantageous over Poly(EtOx) in that they are biocompatible.

[0081] [Table 3]

[0082] (Results of Test Examples 1-4) In the adhesion test using the polymer compound obtained in Example 4, the shear stress was 100 N / cm 2 It was found to have excellent adhesive strength. For reference, Poly(EtOx) (a polymer consisting only of the structural unit represented by formula (1a) above (R is an ethyl group)) has a shear stress of 0.4 N / cm 2In an adhesion test using a mixture of Poly(EtOx) (a polymer consisting only of structural units represented by formula (1a) above (R is an ethyl group)) with 3% dopamine added, the shear stress was 1.0 N / cm 2 This revealed that polymer compounds with a dopamine moiety introduced into the polyoxazoline side chain exhibit high adhesive properties at room temperature.

[0083] (Test Example 2-1) Following the procedure shown in Figure 6, the polymer compound obtained in Example 2, which was evaluated as a surface modifier of the polymer compound, was dissolved in water as a solvent to prepare a polymer solution (surface modifier) ​​with a concentration of 1 mg / mL. 30 μL of this polymer solution was cast onto a silicon wafer and then air-dried for 2 hours to create a polymer compound coating on the silicon wafer. Next, the silicon wafer with the coating was immersed in a Tris-HCl buffer solution with a pH of 8.5 for 10 seconds, and then immersed in distilled water for 1 minute. The coating after immersion in the buffer solution and distilled water was visually observed.

[0084] (Test Example 2-2) The silicon wafers on which the coating was formed were not immersed in a buffer solution, but were immersed only in distilled water during the immersion treatment, except that the immersion treatment was performed in the same manner as in Test Example 2-1.

[0085] (Test Example 2-3) Visual observation of the coating was performed using the same method as in Test Example 2-2, except that the natural drying time was changed to 24 hours.

[0086] (Test Example 2-4) Visual observation of the coating was performed in the same manner as in Test Example 2-1, except that the silicon wafer was replaced with a plasma-treated PTFE substrate.

[0087] (Test example 2-5) Visual observation of the coating was performed in the same manner as in Test Example 2-2, except that the silicon wafer was replaced with a plasma-treated PTFE substrate.

[0088] (Results of Test Examples 2-1 to 2-5) Visual inspection of the coatings revealed that in Test Examples 2-1 and 2-4, which involved immersion in a buffer solution, the formation of a coating was clearly visible. Therefore, it was found that oxidative polymerization occurred quickly and the coating was formed by immersion in a weakly basic pH 8.5 Tris-HCl buffer solution. No peeling of the coating was observed even when the coated substrate was subjected to heat treatment under ultrasonic irradiation conditions. Thus, the polymer compound of the present invention is useful as a surface modifier, and it has been shown that a coating containing the polymer compound can be formed under mild conditions, and in particular, that it can impart biocompatibility to the surface of various materials.

Claims

1. A high-molecular-weight compound having a dopamine moiety in the side chain of a polyoxazoline.

2. The following formula (1) 【Chemistry 1】 The polymer compound according to claim 1, having a structural unit D represented by [the specified structural unit].

3. The polymer compound according to claim 2, which is a copolymer having the structural unit D.

4. An adhesive composition comprising the polymer compound described in any one of claims 1 to 3.

5. A surface modifier comprising the polymer compound described in any one of claims 1 to 3.

6. A method for producing a polymer compound according to any one of claims 1 to 3, The process includes a step of reacting dopamine with a precursor, The aforementioned precursor is The following formula (2a) 【Chemistry 2】 A polymer having structural units represented by, The following equation (2b) 【Transformation 3】 A method for producing a polymer compound, which is a polymer having a structural unit represented by .

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