Composition

Abstract

To provide a composition that can change from a state of high cell adhesion to mammalian cells to a state of low cell adhesion and form a film. [Solution] The composition comprises a shellac-modified compound represented by formula (1) and a plasticizer. In formula (1), Z is the portion of the shellac structure excluding the carboxyl group modified by the functional group Y. TIFF2026060198000012.tif96164

Description

Technical Field

[0001] The present disclosure relates to a composition.

Background Art

[0002] Conventionally, shellac has been used in a wide range of fields. Patent Document 1 discloses a shellac-modified product. In the shellac-modified product, at least one of the hydroxyl group and the carboxyl group in the structure of shellac is chemically modified. The shellac-modified product has cell adhesiveness to mammalian cells. The shellac-modified product can be used, for example, as a material for products in the medical field.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] It is preferable that a composition containing a shellac-modified product can change from a state of high cell adhesiveness to mammalian cells to a state of low cell adhesiveness. In this case, the applications of the composition containing the shellac-modified product are expanded. It is preferable that the composition containing the shellac-modified product can form a film. In one aspect of the present disclosure, it is preferable to provide a composition that can change from a state of high cell adhesiveness to mammalian cells to a state of low cell adhesiveness and can form a film.

Means for Solving the Problems

[0005] (1) One aspect of the present disclosure is a composition containing a shellac-modified product represented by formula (1) and a plasticizer.

[0006]

Chemical Formula

[0007] In formula (1), Z is the part of the shellac structure excluding the carboxyl group modified by the functional group Y. In formula (1), X1, X2, X3, and X4 are each independently a dialkylamino group, an alkylamino group, a hydroxyl group, a halogen group, an alkoxy group, an amino group, an acyl group, an alkyl group, an alkanoate group, or hydrogen. In formula (1), A is oxygen or sulfur.

[0008] One aspect of this disclosure is that a composition can change from a state of high cell adhesion to mammalian cells to a state of low cell adhesion. Furthermore, one aspect of this disclosure is that a composition can form a film.

[0009] (2) Another aspect of the present disclosure is a composition comprising a shellac-modified compound represented by formula (2) and a plasticizer.

[0010] [ka]

[0011] In formula (2), Z is the part of the shellac structure excluding the carboxyl group modified by the functional group Y. In formula (2), A is oxygen or sulfur. Another aspect of this disclosure is that a composition can change from a state of high cell adhesion to mammalian cells to a state of low cell adhesion. Furthermore, another aspect of this disclosure is that a composition can form a film.

[0012] (3) Another aspect of the present disclosure is a composition comprising a shellac-modified compound represented by formula (3) and a plasticizer.

[0013] [ka]

[0014] In formula (3), Z is the part of the shellac structure excluding the carboxy group modified with the functional group Y. In formula (3), X5 is a dialkylamino group, an alkylamino group, a hydroxy group, a halogen group, an alkoxy group, an amino group, an acyl group, an alkyl group, an alkanate group, or hydrogen. In formula (3), A is oxygen or sulfur.

[0015] The composition, which is another aspect of the present disclosure, can change from a state with high cell adhesiveness to a state with low cell adhesiveness with respect to mammalian cells. Further, the composition, which is another aspect of the present disclosure, can form a film.

Brief Description of the Drawings

[0016] [Figure 1] It is an explanatory diagram showing Z, which is the part of the shellac structure excluding the carboxy group modified with the functional group Y. [Figure 2] It is a graph showing the results of mass spectrometry of unmodified shellac and mass spectrometry of DEAC-modified shellac. [Figure 3] It is a graph showing the results of mass spectrometry before light irradiation and mass spectrometry after light irradiation. [Figure 4] It is a graph showing the results of cell proliferation evaluation. [Figure 5] It is a graph showing the relationship between the light irradiation time and the cell recovery rate. [Figure 6] It is a photograph showing cells peeled off from the spin-coated film by light irradiation.

Modes for Carrying Out the Invention

[0017] Exemplary embodiments of the present disclosure will be described with reference to the drawings. 1. Composition Configuration The composition of the present disclosure includes a shellac-modified product and a plasticizer.

[0018] (1-1) Shellac-Modified Product Shellac-modified products are shellac in which the carboxyl groups in the shellac structure have been chemically modified. Shellac is a natural product purified from a resinous substance secreted by the lac insect, which is about 0.6 mm in length, on the branches of certain trees such as those in the legume and mulberry families. The main structure of shellac is, for example, a combination of 1 to 5 constituent units that have been oligoesterified. These constituent units are, for example, esterified between long-chain fatty acids such as aleuritic acid and resin acids such as jalajalic acid and laxijalajalic acid.

[0019] Shellac-modified compounds are represented, for example, by formula (1).

[0020] [ka]

[0021] In formula (1), Z is the part of the shellac structure excluding the carboxyl group modified by the functional group Y. In formula (1), X1, X2, X3, and X4 are each independently a dialkylamino group, an alkylamino group, a hydroxyl group, a halogen group, an alkoxy group, an amino group, an acyl group, an alkyl group, an alkanoate group, or hydrogen. In formula (1), A is oxygen or sulfur.

[0022] Shellac-modified compounds are represented, for example, by formula (2).

[0023] [ka]

[0024] In formula (2), Z is the part of the shellac structure excluding the carboxyl group modified by the functional group Y. In formula (2), A is oxygen or sulfur.

[0025] Shellac-modified compounds can be represented, for example, by formula (3).

[0026] [ka]

[0027] In formula (3), Z is the part of the shellac structure excluding the carboxyl group modified by the functional group Y. In formula (3), X5 is a dialkylamino group, alkylamino group, hydroxyl group, halogen group, alkoxy group, amino group, acyl group, alkyl group, alkanoate group, or hydrogen. In formula (3), A is oxygen or sulfur.

[0028] In formulas (1) to (3), Z has, for example, the structure shown in Figure 1. In Figure 1, R1 is CHO or COOH. In Figure 1, R2 is CH3 or CH2OH. In Figure 1, n is a natural number between 0 and 15. When producing shellac-modified compounds, the carboxyl group to the right of Z in Figure 1 is modified with the functional group Y.

[0029] Examples of dialkylamino groups in X1 to X5 include diethylamino groups. Examples of alkylamino groups in X1 to X5 include ethylamino groups. Examples of halogen groups in X1 to X5 include chloro groups.

[0030] Examples of alkoxy groups in X1 to X5 include methoxy groups. Examples of acyl groups in X1 to X5 include acetyl groups. Examples of alkyl groups in X1 to X5 include methyl groups. Examples of alkanoate groups in X1 to X5 include methanol groups.

[0031] (1-2) Plasticizers Plasticizers include, for example, resins. Examples of plasticizers include dimethyl sebacate, diethyl sebacate, polyvinyl butyral resin, 1,10-decanediol, methyl 12-hydroxystearate, sebatic acid, castor oil, aleuritic acid, myristic acid, 1-octanol, PEG4000, diethylene glycol diethyl ether, and 12-hydroxystearate polymer.

[0032] Polyvinyl butyral resin is preferred as the plasticizer. When the plasticizer contains polyvinyl butyral resin, the water resistance of the film of the composition is further improved. Preferably, the mass ratio of the plasticizer content to the total content of shellac-modified material and plasticizer is 10% by mass or more and 30% by mass or less. In this case, the water resistance of the film of the composition is further improved.

[0033] (1-3) Other ingredients The composition may or may not further contain components other than shellac-modified compounds and plasticizers.

[0034] (1-4) Characteristics of the composition Shellac-modified materials exhibit cell adhesion to mammalian cells. However, when shellac-modified materials are irradiated with light, their cell adhesion to mammalian cells decreases compared to before irradiation. Therefore, shellac-modified materials can change from a state of high cell adhesion to mammalian cells to a state of low cell adhesion. It should be noted that a state of low cell adhesion to mammalian cells is not necessarily limited to a state of no cell adhesion at all. For example, if the cell adhesion is reduced compared to the state without light irradiation, it falls under the category of low cell adhesion.

[0035] Compositions containing shellac-modified materials can also change from a state of high cell adhesion to mammalian cells to a state of low cell adhesion. When reducing the cell adhesion of shellac-modified materials and compositions, the wavelength of light irradiated onto the shellac-modified materials and compositions is, for example, 230 to 600 nm. The irradiation time is, for example, 1 to 720 minutes. When light is irradiated onto shellac-modified materials and compositions, functional group Y is removed from the shellac-modified materials. After the removal of functional group Y, the cell adhesion of shellac and compositions to mammalian cells decreases.

[0036] The compositions of this disclosure can be used, for example, as materials for products in the medical field. Examples of products in the medical field include DDS carriers. The compositions of this disclosure are excellent in, for example, thermosetting properties, film-forming properties, electrical insulation properties, high miscibility with additive components, biodegradability, non-toxicity to living organisms, and properties for sustained release of pharmaceuticals. Films formed using the compositions of this disclosure have high water resistance.

[0037] The composition of this disclosure can be used, for example, as follows: A film of the composition is formed. Mammalian cells are then seeded on the surface of the film. Mammalian cells are then cultured on the film. Since the composition has cell adhesion properties to mammalian cells when not irradiated with light, it is possible to culture mammalian cells on the film of the composition.

[0038] Next, the film is irradiated with light. At this time, functional group Y is removed from the shellac-modified material contained in the composition that makes up the film. After irradiation with light, the cell adhesion of the film to mammalian cells decreases compared to before irradiation with light. As a result, mammalian cells cultured on the film detach from the film while still alive. For example, multiple mammalian cells that have detached from the film remain alive and form a clump. Next, the living mammalian cells that have detached from the film are collected.

[0039] 2. Examples (2-1) Synthesis of DEAC-modified shellac (i) Synthesis of 4-bromomethyl-7-diethylaminocoumarin 6.00 g (25.9 mmol) of 7-diethylamino-4-methylcoumarin (manufactured by Sigma-Aldrich) was placed in a 500 mL three-necked round-bottom flask and degassed by nitrogen purging. Next, 263 mL of anhydrous tetrahydrofuran (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was added to dissolve the 7-diethylamino-4-methylcoumarin.

[0040] Next, with the three-necked round-bottom flask cooled to -78°C in a methanol-dry ice bath, 49.9 mL of lithium bis(trimethylsilyl)amide solution (1.3 mol / L in THF, manufactured by Tokyo Chemical Industry Co., Ltd.) was slowly added dropwise using a dropping funnel. After addition, the mixture was stirred for about 30 minutes.

[0041] Next, a solution of 6.94 g of N-bromosuccinimide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) dissolved in 75.5 mL of anhydrous tetrahydrofuran was slowly added dropwise using a dropping funnel. After addition, the mixture was stirred at -78°C for 30 minutes.

[0042] Next, the reaction was quenched by adding 5.42 mL of 12N hydrochloric acid aqueous solution dropwise. Then, the solvent was removed from the reaction solution under reduced pressure to obtain a residue. The obtained residue was dissolved in 50 mL of dichloromethane and transferred to a separatory funnel, and washed with 50 mL of 5 wt% sodium bicarbonate aqueous solution. After repeating this procedure twice, the organic layer was dehydrated with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure.

[0043] The crude product obtained was subjected to silica gel column chromatography to isolate 1.37 g of the target product. Dichloromethane was used as the developing solvent for silica gel column chromatography. The synthesis yield, based on 4-bromomethyl-7-diethylaminocoumarin, was 17.0%. The synthesis of the compound was confirmed by 1H-NMR.

[0044] (ii) Synthesis of DEAC-modified shellac 5.00 g of shellac (PEARL-N811, manufactured by Gifu Cerac Manufacturing Co., Ltd.) was placed in a 300 mL three-necked round-bottom flask. Next, 30 mL of dehydrated DMF (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was added to dissolve the shellac.

[0045] Next, 1.68 g of potassium carbonate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and 2.29 g of 4-bromomethyl-7-diethylaminocoumarin were added, and the mixture was heated and stirred at 60°C for 3 hours. After cooling to room temperature, potassium carbonate was filtered off the reaction solution by natural filtration. Next, most of the solvent was removed from the filtrate under reduced pressure. Then, shellac was precipitated by adding hexane, a poor solvent.

[0046] Next, the supernatant was discarded, and the resulting precipitate was dissolved in ethanol. Then, the dissolved supernatant was separated, and hexane was added again to induce precipitation. This removed the reaction reagent residue from the shellac.

[0047] Finally, the resulting precipitate was vacuum-dried using a reduced-pressure pump to obtain the desired diethylaminocoumarin-modified shellac (hereinafter referred to as DEAC-modified shellac). The yield was 4.93 g. The reaction yield based on the amount of raw material shellac was 98.6%.

[0048] The DEAC-modified shellac was a shellac-modified compound represented by formula (2). Functional group Y was diethylaminocoumarin. In this example, A in formula (2) was sulfur. In the obtained DEAC-modified shellac, Z was as shown in Figure 1. In Z, R1 was a formyl group or a carboxylic acid group, R2 was a hydroxymethyl group or a methyl group, and n was approximately 0 to 10.

[0049] Furthermore, when DEAC-modified shellac is formed, the bromomethyl group of 4-bromomethyl-7-diethylaminocoumarin reacts with the carboxyl group of the shellac structure. During this reaction, the hydrogen atom of the carboxyl group and the bromine atom of the bromomethyl group are eliminated. The carboxyl group of the shellac structure is modified by diethylaminocoumarin.

[0050] (2-2) Calculation of the functional group introduction rate The functional group introduction rate of DEAC-modified shellac is the ratio of the molar amount of modified carboxyl groups in DEAC-modified shellac to the molar amount of carboxyl groups in the raw material shellac. The functional group introduction rate was calculated using the following method: The molar amount of unmodified carboxyl groups remaining in DEAC-modified shellac (hereinafter referred to as the residual molar amount) was determined by titration using a pH indicator and TFA. Based on the determined residual molar amount, the functional group introduction rate was calculated. The functional group introduction rate was 94.4%.

[0051] (2-3) Confirmation of DEAC-modified shellac synthesis We confirmed that DEAC-modified shellac could be synthesized using electrospray ionization mass spectrometry (ESI-MS). Specifically, the following procedure was performed.

[0052] An ethanol solution of the raw material shellac was prepared. The concentration of the raw material shellac in the ethanol solution was 4 mg / mL. The ethanol solution of raw material shellac was subjected to mass spectrometry using ESI-MS (SYNAPT G2-S HDMS, Waters).

[0053] Furthermore, an ethanol solution of DEAC-modified shellac was prepared. The concentration of DEAC-modified shellac in the ethanol solution was 4 mg / mL. Next, the ethanol solution of DEAC-modified shellac was subjected to ESI-MS and mass spectrometry was performed.

[0054] Figure 2 shows the results of mass spectrometry analysis of raw shellac and DEAC-modified shellac. In Figure 2, "unmodified shellac" refers to the raw shellac. Shellac is a mixture of oligoesters of different lengths, consisting of resin acids such as jalaric acid and laxijalaric acid, and aleuritic acid, a hydroxylated fatty acid. Therefore, mass spectrometry does not yield a single molecular weight peak. However, since each oligoester always has one terminal carboxyl group, when the terminal carboxyl group is modified with diethylaminocoumarin, an increase in molecular weight corresponding to diethylaminocoumarin can be expected for all peaks.

[0055] Mass spectrometry results of DEAC-modified shellac showed that, compared to the mass spectrometry results of raw shellac, the [MH] derived from each oligoester was higher. + [M-Na] + ……MK] + An increase in mass corresponding to diethylaminocoumarin (i.e., a molecular weight of approximately 229) was observed at peaks such as those mentioned above. Diethylaminocoumarin corresponds to functional group Y. From this, it was confirmed that DEAC-modified shellac had been synthesized.

[0056] (2-4) Confirmation that functional group Y is removed from DEAC-modified shellac when irradiated with light. An ethanol solution of DEAC-modified shellac was prepared. The concentration of DEAC-modified shellac in this ethanol solution was 4 mg / mL. Next, the ethanol solution of DEAC-modified shellac was subjected to ESI-MS and mass spectrometry was performed without light irradiation. Mass spectrometry was performed in positive mode, and the changes in the MS peak were tracked. Note that this mass spectrometry was performed before light irradiation.

[0057] Furthermore, the ethanol solution of DEAC-modified shellac prepared as described above was irradiated with 385 nm light using an LED light source (CL-H1-385-9-1-B, manufactured by Asahi Spectroscopy) at room temperature for 2 hours. The irradiation distance was 6.5 cm, and the light intensity was 100%. Next, the ethanol solution of DEAC-modified shellac after light irradiation was subjected to ESI-MS and mass spectrometry was performed. Mass spectrometry was performed in positive mode, and the changes in the MS peak were tracked. Note that this mass spectrometry was performed after light irradiation.

[0058] Figure 3 shows the results of mass spectrometry before and after photoirradiation. In DEAC-modified shellac, diethylaminocoumarin is introduced in the form of a caged ester to the terminal carboxyl group of the shellac oligoester. After the elimination of diethylaminocoumarin by photoirradiation, it was predicted that the DEAC-modified shellac would revert to the chemical structure of the starting material shellac.

[0059] In fact, when comparing the spectrum before and after light irradiation, as shown in Figure 3, the spectrum after light irradiation showed a decrease in molecular weight of approximately 229 for each MS peak derived from the oligoester, corresponding to diethylaminocoumarin, compared to the spectrum before light irradiation. This suggests that, as predicted, diethylaminocoumarin was removed by light irradiation, and the structure returned to that of the raw material shellac.

[0060] (2-5) Preparation of solutions of the composition Solutions S1 to S53 containing the composition were prepared. Solution S1 was prepared by dissolving 150.0 mg of DEAC-modified shellac in ethanol and diluting it to 10 mL.

[0061] Solutions S2 to S53 were each prepared by dissolving 150 mg of a composition containing DEAC-modified shellac and a plasticizer in ethanol and diluting it to 10 mL. The amount of plasticizer added to solutions S2 to S53 and the type of plasticizer are shown in Table 1.

[0062] [Table 1]

[0063] For a solution containing 5% by mass of plasticizer, the solution was prepared by dissolving 150 mg of a composition containing 142.5 mg of DEAC-modified shellac and 7.5 mg of plasticizer in ethanol, and then diluting it to 10 mL.

[0064] For a solution containing 10% by mass of plasticizer, the solution was prepared by dissolving 150 mg of a composition containing 135.0 mg of DEAC-modified shellac and 15.0 mg of plasticizer in ethanol and diluting it to 10 mL.

[0065] For a solution containing 20% ​​by mass of plasticizer, the solution was prepared by dissolving 150 mg of a composition containing 120.0 mg of DEAC-modified shellac and 30.0 mg of plasticizer in ethanol and diluting it to 10 mL.

[0066] For a solution containing 30% by mass of plasticizer, the solution was prepared by dissolving 150 mg of a composition containing 105.0 mg of DEAC-modified shellac and 45.0 mg of plasticizer in ethanol and diluting it to 10 mL.

[0067] (2-6) Evaluation of the film of the composition For each of solutions S1 to S53, the coating properties, flexibility, and water resistance of the composition film were evaluated as follows. The evaluation results are shown in Table 1. In the following, "solution" refers to any of solutions S1 to S53.

[0068] (i) Evaluation of coating properties 200 μL of the solution was weighed into one well of a cell culture vessel (Biolamo; cell culture plate VTC-P6), and gently shaken to distribute the solution throughout the well. Next, the well was left to stand in a drying oven heated to 70°C for 1 hour to evaporate the ethanol contained in the solution. As a result, a film of the composition was formed inside the culture vessel. The mass of the film was 3 mg per well. The film of the composition was observed, and its coating properties were evaluated according to the following criteria. ○: The coating is free from cracks and peeling. ×: The coating is cracked or peeling.

[0069] (ii) Evaluation of flexibility The solution concentration was adjusted so that the solid content concentration was 30% by mass. Next, this solution was applied to a PE film to form a film with a thickness of 20 μm. Then, the PE film was bent at a 90° angle using a 10 mm diameter stainless steel rod as a fulcrum. At this time, the state of the film was observed and its flexibility was evaluated according to the following criteria. ○: The coating does not crack. ×: The coating will crack.

[0070] (iii) Evaluation of water resistance One mL of DMEM medium was added to the film formed in (i) above. Next, it was incubated at 5% CO2 and 37°C. The condition of the film was checked 12 hours after incubation and 3 days after incubation, and the water resistance of the film was evaluated according to the following criteria. ○: No peeling or dissolution of the coating. ×: The coating is peeling or dissolving.

[0071] (2-7) Evaluation of cell adhesion of DEAC-modified shellac film (a1) In the case of DEAC-modified shellac that has not been irradiated with light An ethanol solution of DEAC-modified shellac was prepared. The concentration of DEAC-modified shellac in the ethanol solution was 50 (w / v)%. Using this solution and a spin coater (MS-B100, Mikasa Corporation), a spin-coated film was fabricated on a 15 mm diameter circular coverslip.

[0072] After drying the spin-coated membrane, a round coverslip was placed on the bottom of the 24-well plate. Next, mouse fibroblast cells (NIH3T3) were added in a 1 × 10⁶ solution. 4 The cells were seeded on a spin-coated membrane in a cells / well format. Mouse fibroblasts (NIH3T3 cells) correspond to mammalian cells.

[0073] Next, mouse fibroblasts (NIH3T3 cells) were cultured for a predetermined time in a CO2 incubator using DMEM medium (10% FBS, containing 100 units / mL of penicillin-thleptomycin) under conditions of a CO2 concentration of 5% and a temperature of 37°C. The number of cells was measured 1, 3, and 5 days after the start of culture using Cell Count kit-8 (manufactured by Dojin Chemical Laboratories).

[0074] (b1) In the case of DEAC-modified shellac after photoirradiation Cell proliferation was evaluated in essentially the same manner as in (a1) above. However, after setting a round coverslip on the bottom of the 24-well plate, the spin-coated membrane was irradiated with light. The light source was an LED light (CL-H1-385-9-1-B, Asahi Spectroscopic Co., Ltd.). The light irradiation time was 2 hours. The light intensity was 100%. The irradiation distance was 6.5 cm. After light irradiation, mouse fibroblasts NIH3T3 cells were seeded onto the spin-coated membrane.

[0075] (c1) In the case of a positive control A positive control slide (Matsunami glass, 15 mm diameter) was placed at the bottom of a 24-well plate. Next, mouse fibroblast cells NIH3T3 were introduced at a rate of 1 × 10⁶ 4 Seeds were seeded on the surface of a glass slide using cells / well.

[0076] Next, mouse fibroblasts (NIH3T3 cells) were cultured for a predetermined time in a CO2 incubator using DMEM medium (10% FBS, containing 100 units / mL of penicillin-thleptomycin) under conditions of a CO2 concentration of 5% and a temperature of 37°C. The number of cells was measured 1, 3, and 5 days after the start of culture using Cell Count kit-8 (manufactured by Dojin Chemical Laboratories).

[0077] The measurement results for (a1) to (c1) above are shown in Figure 4. In Figure 4, "No light irradiation" represents the result of (a1). In Figure 4, "2 hours of light irradiation" represents the result of (b1). In Figure 4, "Cover glass" represents the result of (c1).

[0078] For spin-coated films made of DEAC-modified shellac that were not irradiated with light, good cell adhesion and proliferation similar to that of the positive control were observed. On films made of DEAC-modified shellac after light irradiation, cell adhesion and proliferation were clearly lost. This result suggests that light irradiation caused diethylaminocoumarin to be removed from the DEAC-modified shellac, returning its chemical structure to that of shellac without cell adhesion properties, thus effectively eliminating cell adhesion.

[0079] (2-8) Evaluation of the cell adhesion properties of the film of the composition A spin-coated film was prepared on a 15 mm diameter round coverslip using solution S17 and a spin coater (MS-B100, Mikasa Corporation). The spin-coated film corresponds to a coating. After drying the spin-coated film, the round coverslip was placed on the bottom of a 24-well plate. Next, 1 × 10⁶ mouse fibroblast cells (NIH3T3) were added. 4 Cells were seeded on a spin-coated membrane in a cells / well format.

[0080] Next, mouse fibroblast cells (NIH3T3) were cultured for 3 days in a CO2 incubator using DMEM medium (10% FBS, containing 100 units / mL of penicillin-thleptomycin) under conditions of a CO2 concentration of 5% and a temperature of 37°C.

[0081] Next, the number of cells N1 on the spin-coated film was measured using Cell Count kit-8 (manufactured by Dojin Chemical Research Institute). Then, the spin-coated film was irradiated with light. The light source for irradiation was LED light (CL-H1-385-9-1-B, Asahi Spectroscopic Co., Ltd.). The irradiation times were 0.5 hours, 1.0 hours, and 2.0 hours. The light intensity was 100%. The irradiation distance was 6.5 cm.

[0082] Next, pipetting was performed. Then, the cells that had been detached from the spin-coated membrane by pipetting were collected. Next, the cell count N2 of the collected cells was measured using Cell Count kit-8 (manufactured by Dojin Chemical Research Institute). Next, the cell recovery rate (%) was calculated using the following formula 1.

[0083] (Formula 1) (Cell recovery rate) = (N2 / N1) × 100 Figure 5 shows the cell recovery rates for light irradiation times of 0.5 hours, 1.0 hour, and 2.0 hours. Irradiation with LED light for more than 1 hour allowed for the recovery of over 90% of mouse fibroblasts (NIH3T3 cells) cultured on the spin-coated membrane of the composition, without damaging the spin-coated membrane. Furthermore, the recovered cells were detached while retaining their extracellular matrix, as shown in Figure 6. In other words, it was possible to detach the cells with virtually no damage.

[0084] 3. Other Embodiments Although embodiments of the present disclosure have been described above, the present disclosure is not limited to the embodiments described above and can be implemented in various modified forms.

[0085] (1) Shellac-modified compounds represented by either formula (1) or formula (3), other than DEAC-modified shellac, can be produced in basically the same manner as in the examples. In this case, for example, a starting material containing the desired functional group Y can be used instead of 4-bromomethyl-7-diethylaminocoumarin. The starting material containing the desired functional group Y contains, for example, a bromomethyl group. The bromomethyl group reacts with the carboxyl group present in the shellac structure. As a result of this reaction, the hydrogen of the carboxyl group and the bromine of the bromomethyl group are eliminated. The carboxyl group present in the shellac structure is modified by the functional group Y.

[0086] (2) The function of one component in each of the above embodiments may be divided among multiple components, or the function of multiple components may be performed by one component. Also, some of the configurations of each of the above embodiments may be omitted. Also, at least some of the configurations of each of the above embodiments may be added to, replaced with, etc., the configurations of other embodiments.

[0087] (3) In addition to the compositions described above, this disclosure can also be realized in various forms, such as products containing the compositions as components, and methods for manufacturing the compositions.

[0088] [Technical Concept Disclosed in This Specified Specification] [Item 1] A composition comprising a shellac-modified compound represented by formula (1) and a plasticizer.

[0089] [C1] In formula (1), Z is the part of the shellac structure excluding the carboxyl group modified by the functional group Y. In formula (1), X1, X2, X3, and X4 are each independently a dialkylamino group, an alkylamino group, a hydroxyl group, a halogen group, an alkoxy group, an amino group, an acyl group, an alkyl group, an alkanoate group, or hydrogen. In formula (1), A is oxygen or sulfur. [Item 2] A composition comprising a shellac-modified compound represented by formula (2) and a plasticizer.

[0090] [C2] In formula (2), Z is the part of the shellac structure excluding the carboxyl group modified by the functional group Y. In formula (2), A is oxygen or sulfur. [Item 3] A composition comprising a shellac-modified compound represented by formula (3) and a plasticizer.

[0091] [C3] In formula (3), Z is the part of the shellac structure excluding the carboxyl group modified by the functional group Y. In formula (3), X5 is a dialkylamino group, alkylamino group, hydroxyl group, halogen group, alkoxy group, amino group, acyl group, alkyl group, alkanoate group, or hydrogen. In formula (3), A is oxygen or sulfur. [Item 4] A composition described in any one of items 1 to 3, The plasticizer is a composition containing polyvinyl butyral resin. [Item 5] A composition described in any one of items 1 to 4, A composition in which the mass ratio of the content of the plasticizer to the total content of the shellac-modified product and the plasticizer is 10% by mass or more and 30% by mass or less. [Explanation of Symbols]

[0092] Y: Functional group, Z: The part of the shellac structure excluding the carboxyl group modified by functional group Y.

Claims

1. A composition comprising a shellac-modified compound represented by formula (1) and a plasticizer. 【Chemistry 1】 In formula (1), Z represents the part of the shellac structure excluding the carboxyl group modified by the functional group Y. １ , X ２ , X ３ , X ４ Each of these is independently a dialkylamino group, an alkylamino group, a hydroxyl group, a halogen group, an alkoxy group, an amino group, an acyl group, an alkyl group, an alkanoate group, or hydrogen. In formula (1), A is oxygen or sulfur.

2. A composition comprising a shellac-modified compound represented by formula (2) and a plasticizer. 【Chemistry 2】 In formula (2), Z is the part of the shellac structure excluding the carboxyl group modified by the functional group Y. In formula (2), A is oxygen or sulfur.

3. A composition comprising a shellac-modified compound represented by formula (3) and a plasticizer. 【Transformation 3】 In formula (3), Z represents the part of the shellac structure excluding the carboxyl group modified by the functional group Y. ５ A is a dialkylamino group, alkylamino group, hydroxyl group, halogen group, alkoxy group, amino group, acyl group, alkyl group, alkanoate group, or hydrogen. In formula (3), A is oxygen or sulfur.

4. A composition according to any one of claims 1 to 3, The plasticizer is a composition containing polyvinyl butyral resin.

5. A composition according to any one of claims 1 to 3, A composition in which the mass ratio of the content of the plasticizer to the total content of the shellac-modified product and the plasticizer is 10% by mass or more and 30% by mass or less.

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