CN119185668A

CN119185668A - A photocurable material and aqueous humor drainage device and preparation method thereof

Info

Publication number: CN119185668A
Application number: CN202411435450.3A
Authority: CN
Inventors: 王宁利; 王克敏; 任冬妮
Original assignee: Mingche Biotechnology Suzhou Co ltd
Current assignee: Mingche Biotechnology Suzhou Co ltd
Priority date: 2024-10-15
Filing date: 2024-10-15
Publication date: 2024-12-27

Abstract

The invention provides a photocuring material and an aqueous humor drainage device and a preparation method thereof, and relates to the technical field of medical equipment, wherein the photocuring material comprises a component A, a component B and a photoinitiator I, wherein the component A comprises a raw material A1 and a raw material A2, the raw material A1 simultaneously contains an antimetabolite structure, an element F and a sulfhydryl group, the raw material A2 is a sulfhydryl-containing compound, the component B comprises a raw material B1 and a raw material B2, the raw material B1 is at least one of triallyl isocyanurate, trimethylolpropane triacrylate, ethyl acrylate and 2-phenyl ethyl methacrylate, and the raw material B2 is modified gelatin. The invention adopts the sulfhydryl-alkene material with good biocompatibility, and the introduced antimetabolite structure is combined with F element, so that the scar formation of the postoperative operation part can be effectively reduced, the invention has good cell adsorptivity and the drainage efficiency is improved.

Description

Photo-curing material, aqueous humor drainage device and preparation method thereof

Technical Field

The invention relates to the technical field of medical instruments, in particular to a photo-curing material, an aqueous humor drainage device and a preparation method thereof.

Background

At present, most glaucoma diseases clinically can be treated by controlling intraocular pressure through a drainage device implantation operation, and the implanted drainage device can achieve the effects of reducing intraocular pressure and realizing the controlled treatment of glaucoma.

The drainage modes of the glaucoma drainage device mainly comprise a subconjunctival drainage mode, a Schlemm's canal (Schlemm) drainage mode and a choroidal scleral drainage mode. The key point of success of subconjunctival drainage operation is that functional blebs are formed, and the operations have complications such as bleb scarring, bleb thinning and the like, so that glaucoma operation failure can be caused, the physiological path of aqueous humor outflow is mainly Schlemm's canal, the principle is that the physiological drainage channel from anterior chamber to Schlemm's canal is opened to achieve the aim of aqueous humor drainage, the operation is carried out in the prior hospitals, but the drainage operation is not suitable for pigmentary glaucoma with pigmentary trabecular meshwork blockage and open angle glaucoma with subconjunctival vein pressure, and the choroidal scleral drainage mode is a novel aqueous humor drainage mode, avoids some complications possibly generated by functional bleb dependent operations, and can be suitable for pigmentary glaucoma with pigmentary reticular blockage and open angle glaucoma with subconjunctival vein pressure which cannot be treated by Schlemm's canal drainage devices. However, the prior choroidal scleral drainage method has fewer products, and the minimally invasive implantation products suitable for minimally invasive implantation are more rare.

The aqueous humor drainage device for treating glaucoma is a tubular structure which can be implanted in a minimally invasive manner, has an outer diameter of only 100-900 mu m and an inner diameter of 10-100 mu m, is usually very fine, soft and elastic, and can guide aqueous humor out of eyes so as to reduce intraocular pressure.

The research and development of the aqueous humor drainage device have great difficulty, on one hand, the glaucoma minimally invasive drainage tube has extremely small diameter, has high requirements on the preparation process, requires the tube body material to have proper physicochemical properties so as to have the possibility of preparing the drainage tube, on the other hand, the aqueous humor drainage device is required to be safe in use, nontoxic and free of anaphylactic reaction, has no foreign body feeling after implantation, has good compliance with ocular tissues, and has good drainage and depressurization effects.

The existing drainage tube is usually prepared by adopting a photocuring material in a photocuring mode, and the existing photocuring material can meet the performance requirements of good compliance, safe use, no toxicity and the like of the drainage tube and eye tissues, but still has the problem of low drainage efficiency, so that the application of the drainage tube is limited.

Disclosure of Invention

The invention aims to solve the technical problem that the drainage efficiency of an aqueous humor drainage device is low in the prior art, and provides a photocuring material which is capable of reducing scar formation at a postoperative operation part and adjusting hydrophilicity by introducing F element and an antimetabolite structure simultaneously, so that the drainage efficiency of the aqueous humor drainage device is improved, and the problem that the drainage efficiency of the aqueous humor drainage device is low in the prior art is solved.

The technical scheme adopted for solving the technical problems is as follows:

a photo-curing material consists of a component A, a component B and a photoinitiator I;

wherein the A component comprises an A1 raw material and an A2 raw material;

The A1 raw material contains an antimetabolite structure, an F element and a sulfhydryl group;

the A2 raw material is a sulfhydryl-containing compound;

The component B comprises a raw material B1 and a raw material B2;

The raw material B1 is at least one of triallyl isocyanurate, trimethylolpropane triacrylate, ethyl acrylate and 2-phenyl ethyl methacrylate;

The raw material B2 is modified gelatin.

Alternatively, the antimetabolite structure is a thymine structure.

Optionally, the A1 raw material is prepared according to the following method:

S1, mixing trimethylolpropane tri (3-mercaptopropionate), a photoinitiator II and methylene dichloride A to obtain a mixed solution I, dissolving unsaturated alcohol in methylene dichloride B to obtain a mixed solution II, dropwise adding the mixed solution II into the mixed solution I under the irradiation condition of a UV lamp for reaction, and carrying out reduced pressure distillation after the reaction is finished to obtain an intermediate product I;

S2, mixing the intermediate product I, triethylamine and dichloromethane C to obtain a mixed solution III, mixing perfluoroalkyl acyl chloride and dichloromethane D under ice bath condition to obtain a mixed solution IV, dropwise adding the mixed solution IV into the mixed solution III, stirring, standing, filtering, collecting filtrate, washing, standing, separating liquid, collecting an organic phase, drying, filtering, collecting filtrate, distilling under reduced pressure, and vacuum drying to constant weight to obtain an intermediate product II;

s3, under the protection of inert gas, mixing 5-formyl uracil, allylamine, anhydrous magnesium sulfate and dichloromethane E, stirring at 20 ℃, filtering, taking filtrate, distilling under reduced pressure, and drying at normal temperature in vacuum to obtain an intermediate product III;

S4, mixing the intermediate product II, the photoinitiator III and the methylene dichloride F to obtain a mixed solution V, dissolving the intermediate product III in the methylene dichloride G to obtain a mixed solution VI, dropwise adding the mixed solution VI into the mixed solution V under the irradiation condition of a UV lamp to react, and distilling under reduced pressure after the reaction is finished to obtain the raw material A1.

Optionally, the unsaturated alcohol is selected from at least one of 9-decen-1-ol, undecenol, 5-hexenyl-1-ol.

Optionally, the perfluoroalkyl acyl chloride is at least one selected from heptafluorobutyryl chloride and perfluorooctanoyl chloride.

Alternatively, the molar ratio of trimethylolpropane tris (3-mercaptopropionate) to unsaturated alcohol in step S1 is 1 (0.8-1.2), and the photoinitiator II in step S1 is 1wt% of the total mass of the reactants in step S1.

Optionally, in the step S2, the molar ratio of the intermediate product I to the triethylamine to the perfluoroalkyl acyl chloride is 1 (0.8-1.2) to 0.8-1.2.

Optionally, in the step S3, the molar ratio of the 5-formyluracil to the allylamine to the anhydrous magnesium sulfate is 1 (0.8-1.2) to 0.8-1.2.

Optionally, the molar ratio of the intermediate product II to the intermediate product III in the step S4 is 1:1, and the amount of the photoinitiator III in the step S4 is 1wt% of the total mass of the reactants in the step S4.

Optionally, the A2 raw material is at least one selected from 3-mercapto-beta, 4-dimethylcyclohexanediol, bicyclo [2.2.1] heptane-2, 3-dithiol, ethylene glycol bis (3-mercaptopropionate) and trimethylolpropane tris (3-mercaptopropionate).

Optionally, the molar ratio of the A1 raw material to the A2 raw material in the A component is (0.01-0.05) (0.95-0.99).

Optionally, the mass ratio of the B1 raw material to the B2 raw material in the B component is 1:4.

Optionally, the amount ratio of the A component to the B component is 1 (0.95-0.99) in terms of the molar ratio of mercapto groups to carbon-carbon double bonds.

Optionally, the photoinitiator I is used in an amount of 0.5 to 1.5wt% based on the total mass of the reactants.

Another object of the present invention is to provide an aqueous humor drainage device, which is prepared from the above-mentioned light-cured material by a light-curing method.

The invention further aims to provide a preparation method of the aqueous humor drainage device, which comprises the following steps of injecting a light-cured material into a microfluidic mould, irradiating by ultraviolet light, curing, and then placing into 37 ℃ physiological saline for oscillation to obtain the aqueous humor drainage device.

The beneficial effects of the invention are as follows:

The photocuring material provided by the invention adopts a sulfhydryl-alkene material with good biocompatibility, and can be used for preparing the aqueous humor drainage device at normal temperature or low temperature through a photocuring technology, so that the damage of thermal stress to the material in a thermocuring process is avoided, the introduced antimetabolite structure is combined with F element, the scar of a postoperative operation part can be effectively reduced, the postoperative operation part has good cell adsorptivity resistance, the drainage efficiency is improved, and the aqueous humor drainage device has good biocompatibility and mechanical property through the introduction of sulfur-containing material and gelatin into raw materials.

Drawings

The invention will be further described with reference to the drawings and examples.

FIG. 1 is an infrared spectrum of intermediate I in example 1 of the present invention;

FIG. 2 is an infrared spectrum of intermediate II in example 1 of the present invention;

FIG. 3 is an infrared spectrum of intermediate III in example 1 of the present invention;

FIG. 4 is an infrared spectrum of the A1 feedstock in example 1 of the present invention.

Detailed Description

The present invention will now be described in further detail. The embodiments described below are exemplary and intended to illustrate the invention and should not be construed as limiting the invention, as all other embodiments, based on which a person of ordinary skill in the art would obtain without inventive faculty, are within the scope of the invention.

The invention provides a photocuring material, which aims to solve the problem of low drainage efficiency of an aqueous humor drainage device in the prior art, and comprises a component A, a component B and a photoinitiator I, wherein the component A comprises a component A1 and a component A2, the component A1 simultaneously contains an antimetabolite structure, an F element and a sulfhydryl group, the component A2 is a sulfhydryl-containing compound, the component B comprises a component B1 and a component B2, the component B1 is at least one selected from triallyl isocyanurate, trimethylolpropane triacrylate, ethyl acrylate and methacrylic acid-2-phenyl ethyl ester, and the component B2 is modified gelatin.

In order to ensure the smooth molding of the aqueous humor drainage device, the invention preferably prepares the modified gelatin according to the following method:

Mixing gelatin with water, regulating the pH value of the solution to be alkaline by using alkali liquor, then dripping allyl glycidyl ether for reaction, regulating the pH value of the reaction mixture to be neutral by using acid solution, dialyzing for 3 days, and freeze-drying to obtain a B2 raw material, namely modified gelatin, wherein the mass ratio of the gelatin to the allyl glycidyl ether is 20:1.

The component A of the photocuring material contains sulfhydryl groups, and the component B contains carbon-carbon double bonds, so that the aqueous humor drainage device can be prepared from the sulfhydryl-alkene material by a photocuring method.

Because the aqueous humor drainage device needs to be implanted into the body for a long time in the use process, the aqueous humor drainage device can be blocked by the proliferation of the postoperative ciliated cells in the use process, and cells in tissue fluid can be adhered to the aqueous humor drainage device, so that the aqueous humor drainage device is poor in filtration effect and fails finally; according to the invention, an antimetabolite structure and F elements are simultaneously introduced into a system through the raw material A1, wherein the antimetabolite structure can prevent cell division, has excellent antimetabolite effect, can reduce scar formation at a postoperative operation part, and improves drainage and filtration effects, the F elements have low atomic surface energy, so that the raw material A1 is enriched at a material interface, and the antimetabolite structure is combined, so that the antimetabolite effect is further improved, meanwhile, the interface hydrophilicity is regulated by interfaces existing in a large number of F elements, so that the raw material A1 has good antimetabolite adsorptivity, and is beneficial to further improving drainage efficiency, and in addition, because the raw material A1 contains a sulfhydryl structure, the raw material A1 can react with carbon-carbon double bonds in the component B, so that the raw material A1 can be fixed into a material system, free small molecules existing in the system are reduced, and damage to a body caused by the existence of small molecules is avoided.

In order to ensure the antimetabolite effect of the aqueous humor drainage device, the antimetabolite structure is preferably a thymine structure, the thymine structure is utilized to prevent cell division, the scar formation of the postoperative operation part is reduced, and the drainage and filtration effects are improved.

Specifically, the preferred A1 raw material of the invention is prepared according to the following method:

S2, mixing the intermediate product I, triethylamine and dichloromethane C to obtain a mixed solution III, mixing perfluoroalkyl acyl chloride and dichloromethane D under ice bath condition to obtain a mixed solution IV, dripping the mixed solution IV into the mixed solution III, stirring, standing, filtering, taking filtrate, washing, standing, separating liquid, taking an organic phase, drying, filtering, taking filtrate, distilling under reduced pressure, and vacuum drying to constant weight to obtain an intermediate product II;

S4, mixing the intermediate product II, the photoinitiator III and the dichloromethane F to obtain a mixed solution V, dissolving the intermediate product III in the dichloromethane G to obtain a mixed solution VI, dropwise adding the mixed solution VI into the mixed solution V under the irradiation condition of a UV lamp for reaction, and distilling under reduced pressure after the reaction is finished to obtain a target product IV, namely a raw material A1.

Wherein the unsaturated alcohol is at least one selected from 9-decen-1-ol, undecenol and 5-hexenyl-1-ol, and the perfluoroalkyl acyl chloride is at least one selected from heptafluorobutyryl chloride and perfluorooctanoyl chloride.

In the present invention, the photoinitiator I, the photoinitiator II, and the photoinitiator III may be the same or different, and the photoinitiator I, the photoinitiator II, and the photoinitiator III are preferably at least one selected from the group consisting of the photoinitiator 2959, the photoinitiator TPO-L, and the photoinitiator 184.

Methylene chloride a, methylene chloride B, methylene chloride C, methylene chloride D, methylene chloride E, methylene chloride F, methylene chloride G in the present invention are merely labels applied to facilitate distinction during writing, and do not represent distinction in properties or components.

In order to achieve both drainage efficiency and mechanical properties of the aqueous humor drainage device, the molar use ratio of trimethylolpropane tri (3-mercaptopropionate) to unsaturated alcohol in the step S1 is preferably 1 (0.8-1.2), the use amount of the photoinitiator II in the step S1 is 1wt% of the total mass of reactants in the step S1, the molar use ratio of the intermediate product I, triethylamine and perfluoroalkyl acyl chloride in the step S2 is preferably 1 (0.8-1.2), the molar use ratio of 5-formyluracil, allylamine and anhydrous magnesium sulfate in the step S3 is preferably 1 (0.8-1.2), the molar use ratio of the intermediate product II and the intermediate product III in the step S4 is preferably 1:1, and the use amount of the photoinitiator III in the step S4 is 1wt% of the total mass of reactants in the step S4.

The preparation flow of the A1 raw material is as follows:

。

Wherein R is selected from at least one of (CH ₂)₄、(CH₂)₈、(CH₂)₉; n is selected from at least one of 2 and 6).

In the present invention, the raw material A2 is preferably at least one selected from the group consisting of 3-mercapto- β, 4-dimethylcyclohexanediol, bicyclo [2.2.1] heptane-2, 3-dithiol, ethylene glycol bis (3-mercaptopropionate) and trimethylolpropane tris (3-mercaptopropionate).

In order to achieve the drainage efficiency and mechanical properties of the aqueous humor drainage device, the molar ratio of the raw material A1 to the raw material A2 in the component A is preferably (0.01-0.05) (0.95-0.99), and the mass ratio of the raw material B1 to the raw material B2 in the component B is preferably 1:4.

The invention further preferably uses the photo-curing material that the molar ratio of A component to B component is 1 (0.95-0.99), and the photo-initiator I is 0.5-1.5wt% of the total mass of the reactants, namely the photo-initiator I is 0.5-1.5wt% of the total mass of A component and B component.

Another object of the present invention is to provide an aqueous humor diverter prepared from the photocurable material as described above by a photocuring method.

The aqueous humor drainage device provided by the invention is prepared by adopting a sulfhydryl-alkene material with good biocompatibility through a photocuring technology at normal temperature or low temperature, so that the damage of thermal stress to the material in a thermocuring technology can be avoided, the scar formation of a postoperative operation part can be effectively reduced through the combination of an introduced antimetabolite structure and F element, so that the aqueous humor drainage device has good cell adsorptivity and drainage efficiency, and the aqueous humor drainage device has good biocompatibility and mechanical property through the introduction of sulfur-containing material and gelatin as raw materials.

The preparation method of the aqueous humor drainage device provided by the invention is carried out at normal temperature or low temperature by a photo-curing technology, so that the damage of thermal stress to materials in a thermal curing process can be avoided, the scar formation of an operation part after operation can be effectively reduced by combining an introduced antimetabolite structure with F element, so that the aqueous humor drainage device has good cell adsorptivity resistance and drainage efficiency is improved, and the aqueous humor drainage device has good biocompatibility and mechanical property by introducing sulfur-containing materials and gelatin into raw materials.

In order that the above-recited objects, features and advantages of the present invention will become more readily apparent, a more particular description of embodiments of the invention will be rendered by reference to specific embodiments thereof which are illustrated in the appended drawings.

The modified gelatins in the examples of the present invention and comparative examples were prepared as follows, without particular explanation:

5g of gelatin is mixed with 60mL of water, the pH value of the solution is regulated to 10.5 by using a sodium hydroxide aqueous solution with the concentration of 3mol/L, then 0.25g of allyl glycidyl ether is dripped into the solution to react for 4 hours, the pH value of the reaction mixture is regulated to be neutral by using a hydrochloric acid aqueous solution with the concentration of 3mol/L, the reaction mixture is dialyzed for 3 days, and the modified gelatin, namely the raw material B ₂, is obtained by freeze drying.

In the following examples, the content of carbon-carbon double bonds in the starting materials was determined by iodometric titration.

Example 1

The embodiment provides a preparation method of an aqueous humor drainage device, which comprises the following steps:

Mixing the component A, the component B and the photoinitiator 2959, injecting into a microfluidic mould, irradiating for 30s by ultraviolet light with the wavelength of 355nm, curing, and then placing into 37 ℃ physiological saline for oscillation for 7d to obtain the aqueous humor drainage device.

The component A comprises a raw material A1 and a raw material A2, wherein the dosage ratio of the raw material A1 to the raw material A2 is 0.02mol:0.98mol;

the A2 raw material is a mixture of 3-mercapto-beta, 4-dimethylcyclohexanediol and ethylene glycol bis (3-mercaptopropionate) according to the mol ratio of 0.5:0.5.

The component B comprises a raw material B1 and a raw material B2, wherein the dosage ratio of the raw material B1 to the raw material B2 is 2g to 8g;

the raw material B1 is a mixture of triallyl isocyanurate and ethyl acrylate according to the mass ratio of 0.6:1.4.

The molar ratio of the mercapto group to the carbon-carbon double bond of the component A to the component B is 1:0.99, and the dosage of the photoinitiator 2959 is 1.5 weight percent of the total mass of the reactants.

The preparation method of the A1 raw material comprises the following steps:

S1, adding trimethylolpropane tri (3-mercaptopropionate), a photoinitiator TPO-L and dichloromethane A into a flask, dissolving 9-decen-1-ol into dichloromethane B, placing into a constant pressure dropping funnel, magnetically stirring, dropping at constant speed, placing under a UV lamp while the wavelength is 355nm, the light intensity is 400mJ/cm ² min, removing the reaction device after the reaction is finished, and distilling under reduced pressure to obtain an intermediate product I;

Trimethylolpropane tris (3-mercaptopropionate), 9-decen-1-ol in a 1mol:1mol ratio;

The ratio of trimethylol propane tris (3-mercaptopropionate) to methylene chloride A was 1mol:1200mL;

the dosage ratio of 9-decen-1-ol to dichloromethane B was 1mol:450mL;

The dosage of the photo initiator TPO-L is 1wt% of the total mass of the reactants in the step S1;

Referring to fig. 1, the infrared data for intermediate I is shown as 3443cm ^-1 for the presence of-OH, 2550cm ^-1 for the presence and attenuation of-SH, 1733 cm ^-1 for the presence of-c=o, 1631cm ^-1 for the absence of-c=c.

S2, adding an intermediate product I, triethylamine and dichloromethane C into a flask, stirring, placing perfluorooctanoyl chloride and dichloromethane D into a constant pressure dropping funnel, carrying out ice bath, magnetically stirring, dropwise adding at a constant speed, continuing stirring for 8 hours after the dropwise adding is finished, stopping stirring, standing, filtering, taking filtrate, adding a20 wt% dilute hydrochloric acid solution for 3 times, adding a saturated sodium bicarbonate aqueous solution for 3 times, washing with deionized water A for 3 times, standing, separating liquid, taking an organic phase, adding anhydrous sodium sulfate for drying, filtering, taking filtrate, carrying out reduced pressure distillation, and carrying out vacuum drying at 50 ℃ until the weight is constant to obtain an intermediate product II;

The dosage ratio of the intermediate product I, triethylamine and perfluorooctanoyl chloride is 1mol to 1mol;

the dosage ratio of the intermediate I to the dichloromethane C is 1mol:1660mL;

the dosage ratio of perfluorooctanoyl chloride to dichloromethane D is 1mol:1300mL;

Referring to fig. 2, the infrared data for intermediate II is as follows 3443cm ^-1 for-OH disappearance, 2550cm ^-1 for-SH presence, 1733 cm ^-1 for-c=o presence, 1350 cm ^-1 for-C-F presence.

S3, N ₂ is used for protection, 5-formyluracil, allylamine, anhydrous magnesium sulfate and methylene dichloride E are added into a three-neck flask, stirred for 20 hours at 20 ℃, filtered, the filtrate is taken, distilled under reduced pressure, and dried under normal temperature and vacuum, so that an intermediate product III is obtained;

the dosage ratio of the formyluracil, the allylamine and the anhydrous magnesium sulfate is 1mol:1mol;

the dosage ratio of 5-formyl uracil to dichloromethane E was 1mol:420mL;

Referring to FIG. 3, the infrared data for intermediate III is as follows 1555cm ^-1: -NH- (amide) present; 1676cm ^-1: -c=o (ketone group in pyrimidine ring) present, 1612cm ^-1: -c=c- (pyrimidine) present, 1720 cm ^-1、2870 cm^-1、2720 cm^-1: H-c=o (aldehyde group) disappeared, 1634cm ^-1: -c=c-present.

S4, adding an intermediate product II, a photoinitiator TPO-L and dichloromethane F into a flask, dissolving the intermediate product III in dichloromethane G, placing the mixture in a constant pressure dropping funnel, magnetically stirring, dropping the mixture at a constant speed under a UV lamp, wherein the wavelength is 355nm, the light intensity is 400mJ/cm ², and irradiating for 5min;

the dosage ratio of the intermediate II to the intermediate III is 1mol to 1mol;

The ratio of intermediate II to dichloromethane F was 1mol:3000mL;

The ratio of intermediate III to dichloromethane G was 1mol:600mL;

The amount of the photoinitiator TPO-L was 1wt% based on the total mass of the reactants in step S4.

As shown in FIG. 4, the infrared data of the A1 raw material is as follows, 2550cm ^-1 -SH is present and attenuated; 1733 cm ^-1 -c=o (ester group) present; 1350 cm ^-1 -C-F present; 1555cm ^-1 for the presence of-NH- (amide), 1676cm ^-1 for the presence of-C=O (ketone group in pyrimidine ring), 1612cm ^-1 for the presence of-C=C- (pyrimidine), 1634cm ^-1 for the presence of-C=C-disappearance.

Example 2

Mixing the component A, the component B and the photoinitiator TPO-L, injecting into a microfluidic mould, irradiating for 30s by ultraviolet light with the wavelength of 355nm, solidifying, and then placing into 37 ℃ physiological saline for oscillation for 7d to obtain the glaucoma aqueous humor drainage device.

The component A comprises a raw material A1 and a raw material A2, wherein the dosage ratio of the raw material A1 to the raw material A2 is 0.01mol:0.99mol;

The raw material A2 is a mixture of bicyclo [2.2.1] heptane-2, 3-dithiol and ethylene glycol bis (3-mercaptopropionate) according to the mol ratio of 0.3:0.7.

The raw material B1 is a mixture of trimethylolpropane triacrylate, ethyl acrylate and 2-phenyl ethyl methacrylate according to the mass ratio of 0.8:0.8:0.4.

The molar ratio of the mercapto group to the carbon-carbon double bond of the component A to the component B is 1:0.97, and the dosage of the photoinitiator TPO-L is 0.5 weight percent of the total mass of the reactants.

The preparation method of the A1 raw material comprises the following steps:

S1, adding trimethylolpropane tri (3-mercaptopropionate), a photoinitiator 2959 and dichloromethane A into a flask, dissolving undecenol in dichloromethane B, placing the dichloromethane B into a constant pressure dropping funnel, magnetically stirring, dropping at a constant speed, placing under a UV lamp, irradiating for 10min at a wavelength of 355nm and a light intensity of 400mJ/cm ², removing a reaction device after the reaction is finished, and distilling under reduced pressure to obtain an intermediate product I;

Trimethylolpropane tris (3-mercaptopropionate), undecenol in a 1mol:1mol ratio;

The dosage ratio of undecenol to dichloromethane B is 1mol:510mL;

photoinitiator 2959 was used in an amount of 1wt% of the total mass of reactants in step S1.

S2, adding an intermediate product I, triethylamine and dichloromethane C into a flask, stirring, placing perfluorooctanoyl chloride and dichloromethane D into a constant pressure dropping funnel, carrying out ice bath, magnetically stirring, dropwise adding at a constant speed, continuing stirring for 12 hours after the dropwise adding is finished, stopping stirring, standing, filtering, taking filtrate, adding a 20wt% dilute hydrochloric acid solution for 3 times, adding a saturated sodium bicarbonate aqueous solution for 3 times, washing with deionized water A for 3 times, standing, separating liquid, taking an organic phase, adding anhydrous sodium sulfate for drying, filtering, taking filtrate, carrying out reduced pressure distillation, and carrying out vacuum drying at 50 ℃ until the weight is constant to obtain an intermediate product II;

the dosage ratio of intermediate I to dichloromethane C was 1mol:1700mL;

the ratio of perfluorooctanoyl chloride to dichloromethane D was 1mol:1300mL.

the dosage ratio of 5-formyl uracil, allylamine and anhydrous magnesium sulfate is 1mol:1mol;

The 5-formyl uracil was used in a 1mol:420mL ratio to dichloromethane E.

S4, adding an intermediate product II, a photoinitiator 2959 and dichloromethane F into a flask, dissolving the intermediate product III in dichloromethane G, placing the mixture in a constant-pressure dropping funnel, magnetically stirring, dropping the mixture at a constant speed under a UV lamp, wherein the wavelength is 355nm, the light intensity is 400mJ/cm ², and irradiating the mixture for 10min;

The ratio of intermediate II to dichloromethane F was 1mol:3000mL;

The ratio of intermediate III to dichloromethane G was 1mol:600mL;

Photoinitiator 2959 was used in an amount of 1wt% of the total mass of reactants in step S4.

Example 3

the component A, the component B and the photoinitiator 184 are mixed and injected into a microfluidic mould, and are irradiated for 30s by ultraviolet light with the wavelength of 355nm, and are placed into physiological saline with the temperature of 37 ℃ for oscillation for 7d after solidification, so that the glaucoma aqueous humor drainage device is obtained.

The component A comprises a raw material A1 and a raw material A2, wherein the dosage ratio of the raw material A1 to the raw material A2 is 0.03mol:0.97mol;

the A2 raw material is a mixture of ethylene glycol bis (3-mercaptopropionate) and trimethylolpropane tris (3-mercaptopropionate) according to the molar ratio of 0.6:0.4.

The raw material B1 is a mixture of triallyl isocyanurate, ethyl acrylate and 2-phenyl ethyl methacrylate according to the mass ratio of 0.4:0.8:0.8.

The molar ratio of the mercapto group to the carbon-carbon double bond of the component A to the component B is 1:0.97, and the photoinitiator 184 is 1wt% of the total mass of the reactants.

The preparation method of the A1 raw material comprises the following steps:

S1, adding trimethylolpropane tri (3-mercaptopropionate), a photoinitiator 184 and methylene dichloride A into a flask, dissolving 5-hexenyl-1-ol in methylene dichloride B, placing the mixture into a constant pressure dropping funnel, magnetically stirring, dropping the mixture at a constant speed, placing the mixture under a UV lamp, irradiating the mixture for 8min at a wavelength of 355nm and a light intensity of 400mJ/cm ², removing a reaction device after the reaction is finished, and distilling the mixture under reduced pressure to obtain an intermediate product I;

trimethylolpropane tris (3-mercaptopropionate), 5-hexenyl-1-ol in a 1mol:1mol ratio;

The dosage ratio of the 5-hexenyl-1-ol to the dichloromethane B is 1mol:300mL;

The photoinitiator 184 was used in an amount of 1wt% based on the total mass of the reactants in step S1.

S2, adding an intermediate product I, triethylamine and dichloromethane C into a flask, stirring, placing perfluorooctanoyl chloride and dichloromethane D into a constant pressure dropping funnel, carrying out ice bath, magnetically stirring, dropwise adding at a constant speed, continuing stirring for 10 hours after the dropwise adding is finished, stopping stirring, standing, filtering, taking filtrate, adding a 20wt% dilute hydrochloric acid solution for 3 times, adding a saturated sodium bicarbonate aqueous solution for 3 times, washing with deionized water A for 3 times, standing, separating liquid, taking an organic phase, adding anhydrous sodium sulfate for drying, filtering, taking filtrate, carrying out reduced pressure distillation, and carrying out vacuum drying at 50 ℃ until the weight is constant to obtain an intermediate product II;

the ratio of intermediate I to dichloromethane C was 1mol:1500mL;

the ratio of perfluorooctanoyl chloride to dichloromethane D was 1mol:1300mL.

The 5-formyl uracil was used in a 1mol:420mL ratio to dichloromethane E.

S4, adding an intermediate product II, a photoinitiator 184 and methylene dichloride F into a flask, dissolving the intermediate product III in methylene dichloride G, placing the mixture into a constant pressure dropping funnel, magnetically stirring, dropping the mixture at a constant speed, placing the mixture under a UV lamp, and irradiating the mixture for 8min at a wavelength of 355nm and a light intensity of 400mJ/cm ²;

The dosage ratio of the intermediate II to the dichloromethane F is 1mol:2800mL;

The ratio of intermediate III to dichloromethane G was 1mol:600mL;

The photoinitiator 184 was used in an amount of 1wt% based on the total mass of the reactants in step S4.

Example 4

Mixing the component A, the component B and the photoinitiator 2959, injecting into a microfluidic mould, irradiating for 30s by ultraviolet light with the wavelength of 355nm, curing, and then placing into 37 ℃ physiological saline for oscillation for 7d to obtain the glaucoma aqueous humor drainage device.

The raw material A2 is ethylene glycol bis (3-mercaptopropionate).

The raw material B1 is a mixture of trimethylolpropane triacrylate, ethyl acrylate and 2-phenyl ethyl methacrylate according to the mass ratio of 0.3:0.8:0.9.

The molar ratio of the mercapto group to the carbon-carbon double bond of the component A to the component B is 1:0.97, and the dosage of the photoinitiator 2959 is 1wt% of the total mass of the reactants.

The preparation method of the A1 raw material comprises the following steps:

s1, adding trimethylolpropane tri (3-mercaptopropionate), a photoinitiator 2959 and dichloromethane A into a flask, dissolving 9-decen-1-ol in dichloromethane B, placing the mixture in a constant pressure dropping funnel, magnetically stirring, dropping at constant speed, placing the mixture under a UV lamp, irradiating for 10min at a wavelength of 355nm and a light intensity of 400mJ/cm ², removing a reaction device after the reaction is finished, and distilling under reduced pressure to obtain an intermediate product I;

the dosage ratio of 9-decen-1-ol to dichloromethane B was 1mol:450mL;

S2, adding an intermediate product I, triethylamine and dichloromethane C into a flask, stirring, placing heptafluorobutyryl chloride and dichloromethane D into a constant pressure dropping funnel, carrying out ice bath, magnetically stirring, dropwise adding at a constant speed, continuing stirring for 10 hours after the dropwise adding is finished, stopping stirring, standing, filtering, taking filtrate, adding a 20wt% dilute hydrochloric acid solution for 3 times, adding a saturated sodium bicarbonate aqueous solution for 3 times, washing with deionized water A for 3 times, standing, separating liquid, taking an organic phase, adding anhydrous sodium sulfate for drying, filtering, taking filtrate, carrying out reduced pressure distillation, and carrying out vacuum drying at 50 ℃ until the weight is constant to obtain an intermediate product II;

the dosage ratio of the intermediate I to the triethylamine to the heptafluorobutyryl chloride is 1mol to 1mol;

the dosage ratio of the intermediate I to the dichloromethane C is 1mol:1660mL;

the dosage ratio of heptafluorobutyryl chloride to dichloromethane D was 1mol:700mL.

The 5-formyl uracil was used in a 1mol:420mL ratio to dichloromethane E.

S4, adding an intermediate product II, a photoinitiator 2959 and dichloromethane F into a flask, dissolving the intermediate product III in dichloromethane G, placing the mixture in a constant-pressure dropping funnel, magnetically stirring, dropping the mixture at a constant speed under a UV lamp, wherein the wavelength is 355nm, the light intensity is 400mJ/cm ², and irradiating for 8min;

The dosage ratio of the intermediate II to the dichloromethane F is 1mol:2360mL;

The ratio of intermediate III to dichloromethane G was 1mol:600mL;

Example 5

The component A comprises a raw material A1 and a raw material A2, wherein the dosage ratio of the raw material A1 to the raw material A2 is 0.04mol:0.96mol;

the raw material B1 is methacrylic acid-2-phenyl ethyl ester.

The preparation method of the A1 raw material comprises the following steps:

S1, adding trimethylolpropane tri (3-mercaptopropionate), a photoinitiator TPO-L and dichloromethane A into a flask, dissolving 9-decen-1-ol in dichloromethane B, placing the mixture into a constant pressure dropping funnel, magnetically stirring, dropping the mixture at a constant speed, placing the mixture under a UV lamp, irradiating the mixture for 5min at a wavelength of 355nm and a light intensity of 400mJ/cm ², removing a reaction device after the reaction is finished, and distilling the mixture under reduced pressure to obtain an intermediate product I;

The ratio of trimethylolpropane tris (3-mercaptopropionate) to methylene chloride A was 1mol:1200mL, and the ratio of 9-decen-1-ol to methylene chloride B was 1mol:450mL;

The amount of the photoinitiator TPO-L was 1wt% based on the total mass of the reactants in step S1.

the ratio of intermediate I to dichloromethane C was 1mol:1370mL;

The 5-formyl uracil was used in a 1mol:420mL ratio to dichloromethane E.

The ratio of intermediate II to dichloromethane F was 1 mol:207mL;

The ratio of intermediate III to dichloromethane G was 1mol:600mL;

Example 6

The component A comprises a raw material A1 and a raw material A2, wherein the dosage ratio of the raw material A1 to the raw material A2 is 0.05mol:0.95mol;

the A2 raw material is a mixture of 3-mercapto-beta, 4-dimethylcyclohexanediol and ethylene glycol bis (3-mercaptopropionate) according to the mol ratio of 0.8:0.2.

The raw material B1 is a mixture of ethyl acrylate and 2-phenyl ethyl methacrylate according to the mass ratio of 1.4:0.6.

The preparation method of the A1 raw material comprises the following steps:

S1, adding trimethylolpropane tri (3-mercaptopropionate), a photoinitiator TPO-L and dichloromethane A into a flask, dissolving undecenol in dichloromethane B, placing the mixture in a constant pressure dropping funnel, magnetically stirring, dropping at a constant speed, placing under a UV lamp, irradiating for 5min at a wavelength of 355nm and a light intensity of 400mJ/cm ², removing a reaction device after the reaction is finished, and distilling under reduced pressure to obtain an intermediate product I;

Trimethylolpropane tris (3-mercaptopropionate), undecenol in a 1mol:1mol ratio;

The ratio of trimethylolpropane tris (3-mercaptopropionate) to methylene chloride A was 1mol:610mL;

The dosage ratio of undecenol to dichloromethane B is 1mol:510mL;

S2, adding an intermediate product I, triethylamine and dichloromethane C into a flask, stirring, placing heptafluorobutyryl chloride and dichloromethane D into a constant pressure dropping funnel, carrying out ice bath, magnetically stirring, dropwise adding at a constant speed, continuing stirring for 12 hours after the dropwise adding is finished, stopping stirring, standing, filtering, taking filtrate, adding a 20wt% dilute hydrochloric acid solution for 3 times, adding a saturated sodium bicarbonate aqueous solution for 3 times, washing with deionized water A for 3 times, standing, separating liquid, taking an organic phase, adding anhydrous sodium sulfate for drying, filtering, taking filtrate, carrying out reduced pressure distillation, and carrying out vacuum drying at 50 ℃ until the weight is constant to obtain an intermediate product II;

the dosage ratio of the intermediate I to the dichloromethane C is 1mol:1140mL;

The 5-formyl uracil was used in a 1mol:420mL ratio to dichloromethane E.

the ratio of intermediate II to dichloromethane F was 1mol:1840mL;

The ratio of intermediate III to dichloromethane G was 1mol:600mL;

Example 7

the raw material A2 is a mixture of bicyclo [2.2.1] heptane-2, 3-dithiol and ethylene glycol bis (3-mercaptopropionate) according to the mol ratio of 0.5:0.5.

The raw material B1 is a mixture of triallyl isocyanurate and ethyl acrylate according to the mass ratio of 0.8:1.2.

The molar ratio of the mercapto group to the carbon-carbon double bond of the component A to the component B is 1:0.95, and the dosage of the photoinitiator 2959 is 1.5 weight percent of the total mass of the reactants.

The preparation method of the A1 raw material comprises the following steps:

S1, adding trimethylolpropane tri (3-mercaptopropionate), a photoinitiator 184 and methylene dichloride A into a flask, dissolving 9-decen-1-ol in methylene dichloride B, placing the mixture into a constant pressure dropping funnel, magnetically stirring, dropping the mixture at a constant speed, placing the mixture under a UV lamp, irradiating the mixture for 10min at a wavelength of 355nm and a light intensity of 400mJ/cm ², removing a reaction device after the reaction is finished, and distilling the mixture under reduced pressure to obtain an intermediate product I;

the dosage ratio of 9-decen-1-ol to dichloromethane B was 1mol:450mL;

The ratio of intermediate I to dichloromethane C was 1mol:1080mL;

the ratio of perfluorooctanoyl chloride to dichloromethane D was 1mol:1300mL.

The 5-formyl uracil was used in a 1mol:420mL ratio to dichloromethane E.

the dosage ratio of the intermediate II to the dichloromethane F is 1mol:2380mL;

The ratio of intermediate III to dichloromethane G was 1mol:600mL;

Example 8

The raw material A2 is ethylene glycol bis (3-mercaptopropionate).

the raw material B1 is methacrylic acid-2-phenyl ethyl ester.

The molar ratio of the mercapto group to the carbon-carbon double bond of the component A to the component B is 1:0.99, and the photoinitiator 184 is 1wt% of the total mass of the reactants.

The preparation method of the A1 raw material comprises the following steps:

S1, adding trimethylolpropane tri (3-mercaptopropionate), a photoinitiator 184 and methylene dichloride A into a flask, dissolving 9-decen-1-ol in methylene dichloride B, placing the mixture into a constant pressure dropping funnel, magnetically stirring, dropping the mixture at a constant speed, placing the mixture under a UV lamp, irradiating the mixture for 5min at a wavelength of 355nm and a light intensity of 400mJ/cm ², removing a reaction device after the reaction is finished, and distilling the mixture under reduced pressure to obtain an intermediate product I;

the ratio of trimethylolpropane tris (3-mercaptopropionate) to methylene chloride A was 1mol:710mL;

the dosage ratio of 9-decen-1-ol to dichloromethane B was 1mol:450mL;

the ratio of intermediate I to dichloromethane C was 1mol:1180mL;

the ratio of perfluorooctanoyl chloride to dichloromethane D was 1mol:1300mL.

The 5-formyl uracil was used in a 1mol:420mL ratio to dichloromethane E.

S4, adding an intermediate product II, a photoinitiator 184 and methylene dichloride F into a flask, dissolving the intermediate product III in methylene dichloride G, placing the mixture into a constant pressure dropping funnel, magnetically stirring, dropping the mixture at a constant speed, placing the mixture under a UV lamp, irradiating the mixture for 10min at a wavelength of 355nm and a light intensity of 400mJ/cm ², removing a reaction device after the reaction is finished, and distilling the mixture under reduced pressure to obtain a target product IV, namely a raw material A1;

the dosage ratio of the intermediate II to the dichloromethane F is 1mol:2480mL;

The ratio of intermediate III to dichloromethane G was 1mol:600mL;

The aqueous humor drainage device provided by each comparative example below is compared with example 1:

Comparative example 1

This comparative example differs from example 1 in that the amount of the A component to the B component is 1:1.2 in terms of the molar ratio of mercapto groups to carbon-carbon double bonds.

Comparative example 2

This comparative example differs from example 1 in that the amount of the A component to the B component is 1:0.8 in terms of the molar ratio of mercapto groups to carbon-carbon double bonds.

Comparative example 3

This comparative example differs from example 1 in that the a component comprises only A2 starting material.

Comparative example 4

This comparative example differs from example 1 in that the ratio of the amount of A1 starting material to the amount of A2 starting material was 0.1mol:0.9mol.

Comparative example 5

This comparative example differs from example 1 in that the B component comprises only the B2 raw material.

Comparative example 6

This comparative example differs from example 1 in that the ratio of the amount of B1 starting material to B2 starting material was 4 g/6 g.

Comparative example 7

This comparative example differs from example 1 in that the starting material B2 is gelatin, i.e. gelatin has not been modified.

Comparative example 8

This comparative example differs from example 1 in that the starting material A1 is 5-formyluracil.

Comparative example 9

This comparative example differs from example 1 in that the process for preparing the A1 feedstock is as follows:

S1, N ₂ is used for protection, 5-formyluracil, allylamine, anhydrous magnesium sulfate and methylene dichloride E are added into a three-neck flask, stirred for 20 hours at 20 ℃, filtered, the filtrate is taken, distilled under reduced pressure, and dried under normal temperature and vacuum, so that an intermediate product I is obtained;

The 5-formyl uracil was used in a 1mol:420mL ratio to dichloromethane E.

S2, adding trimethylolpropane tri (3-mercaptopropionate), a photoinitiator TPO-L and dichloromethane F into a flask, dissolving an intermediate product I in dichloromethane G, placing the mixture in a constant-pressure dropping funnel, magnetically stirring, dropping at a constant speed, placing the mixture under a UV lamp, irradiating for 5min at a wavelength of 355nm and a light intensity of 400mJ/cm ², removing a reaction device after the reaction is finished, and distilling under reduced pressure to obtain a target product;

trimethylolpropane tris (3-mercaptopropionate), intermediate I in a 1mol:1mol ratio;

the ratio of trimethylol propane tris (3-mercaptopropionate) to methylene chloride F was 1mol:1200mL;

the dosage ratio of the intermediate I to the dichloromethane G is 1mol:1660mL;

the amount of the photoinitiator TPO-L was 1wt% based on the total mass of the reactants in step S2.

Comparative example 10

the dosage ratio of 9-decen-1-ol to dichloromethane B was 1mol:450mL;

S2, adding an intermediate product I, triethylamine and dichloromethane C into a flask, stirring, placing perfluorooctanoyl chloride and dichloromethane D into a constant pressure dropping funnel, carrying out ice bath, magnetically stirring, dropwise adding at a constant speed, continuing stirring for 8 hours after the dropwise adding is finished, stopping stirring, standing, filtering, taking filtrate, adding a 20wt% dilute hydrochloric acid solution for 3 times, adding a saturated sodium bicarbonate aqueous solution for 3 times, washing with deionized water A for 3 times, standing, separating liquid, taking an organic phase, adding anhydrous sodium sulfate for drying, filtering, taking filtrate, carrying out reduced pressure distillation, and carrying out vacuum drying at 50 ℃ until the weight is constant to obtain a target product;

the dosage ratio of the intermediate I to the dichloromethane C is 1mol:1660mL;

the ratio of perfluorooctanoyl chloride to dichloromethane D was 1mol:1300mL.

The performance of the aqueous humor drainage device prepared by each embodiment of the invention and the comparative example is respectively measured, and the test method is as follows:

(1) Cell inhibition effect test:

The effect of cell inhibition was evaluated by the response of the cells, primary fibroblasts (10 cells/well) were cultured with fire Kong Peiyang base (DMEM) containing 10% by mass of fetal bovine serum. After the fibroblast cell was precipitated, the migration test was inserted into the glaucoma drainage tube so that it was completely immersed in the medium. After 5 days of culture, the status of fibroblasts was examined with live/dead staining and CCK-8, and the 5-day live/dead ratio of fibroblasts (HTFs) was calculated, the higher the activity of the fibroblasts, the more severe the scarring.

(2) Cell adhesion test:

3T3 mouse embryo bromoblasts were maintained in T-75 Falcon cell culture using sterile Dulbecco's modified French Kong Peiyang base (DMEM) containing 10% Fetal Bovine Serum (FBS) and 100 units/ml penicillin and 0.1 mg/ml streptomycin by mass fraction. 6 samples (36 samples total) of each overlay were placed in 6 well tissue culture plates and irradiated under ultraviolet light for 10-15 minutes. Cells were seeded onto the cover film at a density of approximately 11 000 cells/cm. Cells were then incubated 24h at 37 ℃ with 5% carbon dioxide, and the medium was then decanted and gently rinsed once with PBS. The adherent cell number is defined as the number of viable cells per 100 x field. The percentage of control was calculated by multiplying the ratio of the percentage of viable cells on the treated substrate to the percentage of viable cells on the untreated substrate by 100. The average control adhesion per sample group was determined and statistical comparisons of the viability assays were made as described above.

(3) Water contact angle the raw materials in the examples were injected in proportions to form films and tested with reference to the GB/T30693-2014 measurement.

(4) Monomer residue test-using gas chromatography test. The monomer residue was expressed by <1ppm and >1ppm was expressed as "OK".

(5) And (3) mechanical strength test, namely after the drainage tube is folded in half, observing whether a crack crease phenomenon exists. The mechanical strength was expressed by marking "O" with no crack and no crease "<", marking "+" with crack and crease "".

(6) Elastic modulus test in examples raw materials were injected in proportions into a 5B dumbbell mold for curing, and tested with reference to GB/T1040.3-2006.

(7) Drainage efficiency test 10ml of deionized water was passed through the drain tube at a constant flow rate (64. Mu.l/min) and the time required for the ionized water to completely run out was recorded to determine drainage efficiency.

The test results are shown in Table 1:

。

First, as can be seen from examples 1 to 8 and comparative examples 1 to 10 in table 1, the aqueous humor drainage devices prepared in each example of the present invention have excellent characteristics of cell proliferation resistance and cell adhesion resistance, and simultaneously have suitable water contact angle (hydrophilicity) and drainage efficiency, excellent mechanical properties, and extremely low monomer residue.

Second, it can be observed from examples 1 and comparative examples 1-2 that the mechanical properties of the prepared drainage tube are deteriorated due to the excessive amount of either component by adjusting the reaction ratio of mercapto groups to carbon-carbon double bonds.

Third, it can be seen from examples 1 and comparative examples 3 to 4 that the shortage of the functional raw material A1 in the A-component resulted in the lack of anti-cell proliferation and anti-cell adhesion properties, and that the excessive amount resulted in the deterioration of hydrophilicity.

Fourth, it can be observed from examples 1 and comparative examples 5 to 7 that unreasonable amounts of the B1 raw material in the B component affect the deterioration of mechanical properties, and that unmodified gelatin is used as a filler, so that the thiol and alkene materials have excessive crosslinking density in reaction, and are difficult to mold, and the drainage tube cannot be prepared.

Fifth, it can be observed that the addition of only 5-formyluracil in example 1 and comparative examples 8 to 10 causes problems of poor cell adhesion resistance and excessive monomer residue, that the addition of only mercapto-modified 5-formyluracil also causes problems of poor cell adhesion resistance and risk of drain blockage, and that the addition of only mercapto-modified fluorine-containing structure causes problems of insufficient cell proliferation resistance, and that HTFs have an increased cell activity/death ratio and an increased risk of scarring after 5 days.

With the above-described preferred embodiments according to the present invention as an illustration, the above-described descriptions can be used by persons skilled in the relevant art to make various changes and modifications without departing from the scope of the technical idea of the present invention. The technical scope of the present invention is not limited to the description, but must be determined according to the scope of claims.

Claims

1. A photocurable material, characterized in that it consists of component A, component B and photoinitiator I;

The A component includes A1 raw material and A2 raw material;

The A1 raw material contains antimetabolism structure, F element and thiol group at the same time;

The A2 raw material is a thiol-containing compound;

The B component includes B1 raw material and B2 raw material;

The B1 raw material is selected from at least one of triallyl isocyanurate, trimethylolpropane triacrylate, ethyl acrylate, and 2-phenylethyl methacrylate;

The B2 raw material is modified gelatin;

The A1 raw material is prepared as follows:

S1: Mix trimethylolpropane tris(3-mercaptopropionate), photoinitiator II, and dichloromethane A to obtain a mixed solution I; dissolve unsaturated alcohol in dichloromethane B to obtain a mixed solution II; under UV light irradiation, dropwise add the mixed solution II to the mixed solution I to react; after the reaction is completed, perform vacuum distillation to obtain an intermediate product I;

S2: Mix the intermediate product I, triethylamine and dichloromethane C to obtain a mixed solution III; mix perfluoroalkyl acyl chloride and dichloromethane D under ice bath conditions to obtain a mixed solution IV; dropwise add the mixed solution IV to the mixed solution III, stir, react, let stand, filter, take the filtrate, wash; let stand, separate the liquids, take the organic phase, dry, filter, take the filtrate, distill under reduced pressure, and vacuum dry to constant weight to obtain an intermediate product II;

S3: Under inert gas protection, 5-formyluracil, allylamine, anhydrous magnesium sulfate and dichloromethane E are mixed, stirred at 20°C, filtered, and the filtrate is distilled under reduced pressure and dried under vacuum at room temperature to obtain intermediate III;

S4: Mix the intermediate product II, photoinitiator III and dichloromethane F to obtain a mixed solution V; dissolve the intermediate product III in dichloromethane G to obtain a mixed solution VI; add the mixed solution VI dropwise to the mixed solution V under UV lamp irradiation to react; after the reaction is completed, perform reduced pressure distillation to obtain the A1 raw material.

2 . The photocurable material according to claim 1 , wherein the anti-metabolism structure is a thymine structure.

3. The photocurable material according to claim 1, wherein the unsaturated alcohol is selected from at least one of 9-decen-1-ol, undecenol, and 5-hexenyl-1-ol.

4 . The photocurable material according to claim 1 , wherein the perfluoroalkyl acyl chloride is selected from at least one of heptafluorobutyryl chloride and perfluorooctanoyl chloride.

5. The photocurable material according to claim 1, characterized in that the molar ratio of trimethylolpropane tris(3-mercaptopropionate) to the unsaturated alcohol in step S1 is 1:(0.8-1.2); the amount of the photoinitiator II in step S1 is 1wt% of the total mass of the reactants in step S1.

6. The photocurable material according to claim 1, characterized in that the molar ratio of the intermediate product I, the triethylamine and the perfluoroalkyl acyl chloride in step S2 is 1:(0.8-1.2):(0.8-1.2).

7 . The photocurable material according to claim 1 , wherein the molar ratio of the 5-formyluracil, the allylamine and the anhydrous magnesium sulfate in step S3 is 1:(0.8-1.2):(0.8-1.2).

8. The photocurable material according to claim 1, characterized in that the molar ratio of the intermediate product II to the intermediate product III in step S4 is 1:1; and the amount of the photoinitiator III in step S4 is 1wt% of the total mass of the reactants in step S4.

9. The photocurable material according to any one of claims 1 to 8, characterized in that the A2 raw material is selected from at least one of 3-mercapto-β,4-dimethylcyclohexaneethanethiol, bicyclo[2.2.1]heptane-2,3-dithiol, ethylene glycol bis(3-mercaptopropionate), and trimethylolpropane tris(3-mercaptopropionate).

10 . The photocurable material according to claim 1 , wherein the molar ratio of the A1 raw material to the A2 raw material in the A component is (0.01-0.05):(0.95-0.99).

11 . The photocurable material according to claim 1 , wherein the mass ratio of the B1 raw material to the B2 raw material in the B component is 1:4.

12. The photocurable material according to any one of claims 1 to 8, characterized in that the usage ratio of the component A to the component B is 1:(0.95-0.99) in terms of the molar ratio of mercapto group to carbon-carbon double bond.

13. The photocurable material according to any one of claims 1 to 8, characterized in that the amount of the photoinitiator I is 0.5-1.5 wt % of the total mass of the reactants.

14. An aqueous humor drainage device, characterized in that it is prepared by a photocuring method using the photocurable material according to any one of claims 1 to 13.

15. A method for preparing an aqueous humor drainage device as claimed in claim 14, characterized in that it comprises the following steps: injecting a photocurable material into a microfluidic mold, irradiating it with ultraviolet light, and placing it in 37°C physiological saline for oscillation after curing to obtain an aqueous humor drainage device.