Zwitterionic polyurethane or zwitterionic polyurethane precursor as well as preparation method and application thereof

Abstract

The invention relates to zwitterionic polyurethane or a zwitterionic polyurethane precursor as well as a preparation method and application thereof. The preparation method comprises the following steps: synthesizing ester bond-containing zwitterionic precursor diol, polymerizing with polyisocyanate to obtain polyurethane, and blocking by a single-ended amino or hydroxyl monomer to form a zwitterionic polyurethane precursor; the precursor is further subjected to a covalent bond cleavage reaction, and final zwitterionic polyurethane is generated. The obtained zwitterionic polyurethane and the zwitterionic polyurethane precursor material have controllable mechanical properties, support extrusion, injection molding, photocuring and other processing modes, and are suitable for the fields of medical instruments, drug delivery carriers, medical beauty filling and industrial and civil anti-biofouling. The zwitterionic structure endows the hydrogel with excellent properties of protein adsorption resistance, cell adhesion resistance, biofilm formation resistance, oxidation resistance, wound healing promotion and the like, and the hydrogel can be widely applied to various application fields. The polyurethane can also be used as a flexibilizer to be blended with various polymers, and is good in compatibility and free of phase separation.

Description

Technical Field

[0001] This invention relates to the field of polymer synthesis, and in particular to a zwitterionic polyurethane or a zwitterionic polyurethane precursor, its preparation method, and its application. Background Technology

[0002] Biomedical devices are frequently exposed to complex in vivo / in vitro environments. Adhesion from biomolecules and macroorganisms can lead to a range of adverse complications. For example, upon contact with whole blood, proteins and cells in the blood rapidly adhere to the device surface, followed by activation of clotting factors, platelet adhesion, activation, and aggregation, ultimately leading to thrombus formation. When a device is implanted in the body, the body's immune system recognizes it as a foreign object and encapsulates it with a dense collagen capsule. Microbial adhesion to the device surface can lead to biofilm formation, potentially causing infection. If bacterial infection occurs, an excess of reactive oxygen species (ROS) generated during normal aerobic metabolism is produced. The persistent overproduction of free radicals can lead to an inflammatory state.

[0003] Polyethylene glycol (PEG) is the most widely used non-polluting or low-polluting material. However, PEG is easily oxidized, which limits its long-term in vivo application. Amphoteric materials, including carboxybetaine, sulfobetaine, and phosphorylcholine chemicals, have emerged as an important class of robust, ultra-low-polluting biomaterials. Among them, carboxybetaine has been shown to adsorb only <0.3 ng / cm³ even in 100% plasma or serum. 2 Proteins. Currently, the most common method for incorporating zwitterions into materials is surface coating. This is because pure zwitterionic materials often have poor mechanical properties, insufficient to support the normal operation of most devices. However, the harsh conditions of coating processes and the difficulty in achieving stable, uniform, and high-density zwitterionic polymers on the material surface limit its long-term development. Integrating zwitterions into the bulk material is a better option.

[0004] In an effort to combine zwitterions and antioxidant properties, some natural polysaccharides have been used to graft zwitterions; however, the grafting rate is low and cannot meet application requirements. Summary of the Invention

[0005] To address the problems of existing medical polyurethanes in application, such as immunogenicity, susceptibility to thrombosis and microbial infection, and limited lifespan, this invention provides a long-lasting zwitterionic polyurethane or a zwitterionic polyurethane precursor, its preparation method, and its application.

[0006] The objective of this invention can be achieved through the following technical solutions:

[0007] The present invention first provides a zwitterionic polyurethane or a zwitterionic polyurethane precursor, wherein the zwitterionic polyurethane contains one or more zwitterionic groups, or contains one or more zwitterionic precursor groups, or contains both zwitterionic groups and zwitterionic precursor groups.

[0008] The zwitterionic precursor group refers to a group that can be converted into a zwitterionic group through hydrolysis, chemical reaction, heat, radiation, electricity, oxidation, reduction, acid or alkali treatment.

[0009] The zwitterionic group is selected from carboxybetaine, which refers to a molecular structure containing a carboxylic acid anion and an amino cation, and the molecular structure includes the following structure:

[0010]

[0011] R1 is independently selected from -(CH2)2-, -(CH2)3-, and -(CH2). r -、-(CH2) n O(CH2) s -、-(CH2CH2OCH2CH2) t -, -CH2CH2(OCH2CH2) u - one or more of them;

[0012] R2 is independently selected from -(CH2)2-, -(CH2)3-, and -(CH2). r -、-(CH2) n O(CH2) s -、-(CH2CH2OCH2CH2) t -, -CH2CH2(OCH2CH2) u - one or more of them;

[0013] R3 is independently selected from -CH2-, -(CH2)2-, and -(CH2). r -、-(CH2) n O(CH2) s -、-(CH2CH2OCH2CH2) t -, -CH2CH2(OCH2CH2) u - one or more of them;

[0014] R4 is independently selected from -O-, -NH-, or -S-.

[0015] R5 is independently selected from -H, -CH3, and -(CH2). v One or more of the following: CH3, -C(CH3)3, alkyl, alkenyl, alkynyl, polyester, polyether, polyamide, monosaccharide, oligosaccharide, polysaccharide or glycoside;

[0016] R7 is independently selected from H-, CH3-, CH3CH2-, and CH3(CH2). y -, CH3O-(CH2CH2O) z CH2CH2-, one or more of the following: ethyl bromoacetate, methyl bromoacetate, alkyl bromoacetate, tert-butyl bromopropionate, methyl bromopropionate, tert-butyl bromopropionate, alkyl bromopropionate, tert-butyl bromobutyrate, methyl bromobutyrate, tert-butyl bromobutyrate, and alkyl bromobutyrate.

[0017] A - Independently selected from F - Cl - ,Br - I - SO4 2- NO3 - CO3 2- PO4 3- SiO3 2- ClO4 - CrO4 2- PF6 - BF4 - CF3SO3 - SiF6 2- CN - SCN - OCN - HCOO - CH3COO - C2O4 2- C6H5O7 3- C6H5COO - CF3COO - CF3SO3 - N(CF3SO2)2 2- One or more organic or inorganic anions;

[0018] M + Independently selected from Li + Na + K + Ca 2+ Mg 2+ Fe 2+ Fe 3+ Zn 2+ Inorganic metal cations, or one or more organic cations selected from quaternary ammonium cations, phosphonium cations, etc.;

[0019] Where n, r, s, t, u, v, and y are independent integers selected from 1 to 1000;

[0020] The polymer has a molecular weight of approximately 1,000 to approximately 1,000,000 g / mol.

[0021] The molecular structure of the zwitterionic polyurethane or zwitterionic polyurethane precursor is selected from one of the following:

[0022]

[0023]

[0024] Where x, y, and n are integers selected from 1 to 1000.

[0025] R1 is selected from -(CH2)2-, -(CH2)3-, and -(CH2). m -、-(CH2) r O(CH2) o -、-(CH2CH2OCH2CH2) p -, -CH2CH2(OCH2CH2) v - one or more of them;

[0026] R2 is selected from -(CH2)2-, -(CH2)3-, and -(CH2). m -、-(CH2) r O(CH2) o -、-(CH2CH2OCH2CH2) p -, -CH2CH2(OCH2CH2) v - one or more of them;

[0027] R3 is selected from -CH2-, -(CH2)2-, and -(CH2). m -、-(CH2) r O(CH2) o -、-(CH2CH2OCH2CH2) p -, -CH2CH2(OCH2CH2) v - one or more of them;

[0028] R4 is selected from -O-, -NH-, or -S-;

[0029] R5 is selected from -H, -CH3, and -(CH2). t CH3, -C(CH3)3, alkyl, alkenyl, alkynyl, carbonyl, targeting ligand, peptide, polyester, polyether, polyamide, monosaccharide, oligosaccharide, polysaccharide or glycoside, or one or more of these;

[0030] The polyisocyanate containing R6 is selected from one or more of the following: toluene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, hexamethylene diisocyanate trimer, dicyclohexylmethane diisocyanate, naphthalene diisocyanate, isophthalimethylene diisocyanate, terephthalimethylene diisocyanate, cyclohexylmethylene diisocyanate, isosorbide diisocyanate, ethylene glycol diisocyanate, triphenylmethane triisocyanate, propylene glycol diisocyanate, or bis(2-isocyanate ethyl) sulfide.

[0031] Polyols containing R7 are selected from ethylene glycol (EG), propylene glycol (PG), 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol (BDO), neopentyl glycol (NPG), 1,2,3-propanetriol (glycerol), 1,2,3-butanetriol, 1,2,6-hexanetriol, glycerol (glycerol), erythritol, sorbitol, mannitol, xylitol, 2,5- One or more of the following: furanyl dimethyl alcohol, 2-amino-5-(2-hydroxyethyl)-4(3H)-pyrimidinone, polyether polyol, polyester polyol, polybutane glycol, polytetramethylene ether glycol (PTMEG), polytetrahydrofurfuryl alcohol, polycaprolactone polyol, polylactic acid polyol, polycarbonate polyol, polyamide polyol, polysiloxane polyol, polyacrylate polyol, polysulfone polyol, polyisobutylene polyol, polystyrene polyol, polyurethane polyol, polyisocyanate polyol, polyesteramide polyol, or polyepoxy resin polyol;

[0032] Molecules containing R8 and R9 are selected from polyols containing R5, polyols with zwitterionic or zwitterionic precursor groups, alcohols, amines, carboxylic acids, and CH3(CH2). w OH, methanol, ethanol, propanol, isopropanol, isobutanol, butanol, hexanol, pentanol, alkyl alcohols, aromatic alcohols, CH3(CH2) uNH2, methylamine, ethylamine, propylamine, isopropylamine, isobutylamine, butylamine, hexylamine, pentanamine, alkylamine, aromatic amine, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 6-hydroxyhexyl acrylate, glyceryl acrylate, glyceryl methacrylate, 4-hydroxyphenyl acrylate, 4-hydroxyphenyl methacrylate, 3-(N,N-dimethylamino)propyl acrylate, 3-(N,N-dimethylamino)propyl methacrylate, hydroxyl-terminated polyethylene glycol acrylate, hydroxyl-terminated polyethylene glycol methacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, hydroxyl-terminated polypropylene glycol acrylate, hydroxyl-terminated polypropylene glycol methacrylate, hydroxyl-terminated polytetramethylene ether glycol diacrylate, hydroxyl-terminated polytetramethylene ether glycol dimethacrylate Acrylates, hydroxyl-containing polyurethane acrylates, hydroxyl-containing polyester acrylates, hydroxyl-terminated polyester methacrylates, hydroxyl-containing polyether acrylates, hydroxyl-terminated polyether methacrylates, 2-hydroxy-3-propyl acrylate, 2-hydroxy-3-butyl acrylate, 2-hydroxy-3-methylbutyl acrylate, 2-hydroxyethyl-2-methylpropyl acrylate, 2-hydroxyethyl-3-methylbutyl acrylate, 2-hydroxyethyl-4-methylpentyl acrylate, 3-hydroxy-3-methylbutyl methacrylate, tetraphenylvinyl alcohol, 9,10-dihydroxyanthracene, 2-hydroxy-1,8-naphthalimide, 9-hydroxyfluorenone, hydroxycoumarin hydroxy derivatives, hydroxyl-containing fluorescein (such as 5,6-dihydroxyfluorescein), hydroxyl-containing porphyrin derivatives, hydroxyl-containing benzothiazole and benzimidazole derivatives, hydroxyl-containing stilbene derivatives, and hydroxyl-containing polystyrene derivatives, one or more of these.

[0033] Where m, r, o, p, v, t, w, and u are independent integers selected from 1 to 1000.

[0034] Preferably, the molecular structure of the zwitterionic polyurethane is selected from one of the following:

[0035]

[0036] Where x, y, and n are integers selected from 1 to 1000.

[0037] R1 is selected from -(CH2)2- or -(CH2)3-; R2 is selected from -(CH2)2- and -(CH2)3-; R3 is selected from -CH2- and -(CH2)2-; R4 is selected from one or more of hexamethylene diisocyanate, hexamethylene diisocyanate trimer, isophorone diisocyanate, and dicyclohexylmethane diisocyanate; R5 is selected from one or more of ethylene glycol (EG), propylene glycol (PG), 1,3-propanediol, 1,4-butanediol, polybutanediol, polycarbonate polyol, polytetramethylene ether glycol, and polyester polyol; R6 is selected from -H, -CH3, -CH2CH3, and -C(CH3)3; R7 is selected from -OCH3, -OCH2CH3, methanol, ethanol, propanol, hydroxyethyl acrylate, and hydroxyethyl methacrylate.

[0038] The polymer molecular weight ranges from 1,000 to 1,000,000 g / mol.

[0039] In one embodiment of the present invention, the zwitterionic precursor group can be converted into a zwitterionic group by hydrolysis.

[0040] In one embodiment of the present invention, preferably, the molecular structure of the zwitterionic polyurethane is selected from one of the following:

[0041]

[0042] Where x, y, and n are integers selected from 1 to 1000.

[0043] R1 is selected from -(CH2)2-, -(CH2)3-, and -(CH2). m -、-(CH2) r O(CH2) o -、-(CH2CH2OCH2CH2) p -, -CH2CH2(OCH2CH2) v - one or more of them;

[0044] R2 is selected from -(CH2)2-, -(CH2)3-, and -(CH2). m -、-(CH2) r O(CH2) o -、-(CH2CH2OCH2CH2) p -, -CH2CH2(OCH2CH2) v - one or more of them;

[0045] R3 is selected from -CH2-, -(CH2)2-, and -(CH2). m -、-(CH2) r O(CH2) o-、-(CH2CH2OCH2CH2) p -, -CH2CH2(OCH2CH2) v - one or more of them;

[0046] The polyisocyanate containing R4 is selected from one or more of the following: toluene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, dicyclohexylmethane diisocyanate, naphthalene diisocyanate, isophthalimethylene diisocyanate, terephthalimethylene diisocyanate, cyclohexylmethylene diisocyanate, isosorbide diisocyanate, ethylene glycol diisocyanate, triphenylmethane triisocyanate, propylene glycol diisocyanate, and bis(2-isocyanate ethyl) sulfide.

[0047] Polyols containing R5 are selected from ethylene glycol (EG), propylene glycol (PG), 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol (BDO), neopentyl glycol (NPG), 1,2,3-propanetriol (glycerol), 1,2,3-butanetriol, 1,2,6-hexanetriol, glycerol (glycerol), erythritol, sorbitol, mannitol, xylitol, 2,5-furandimethyl, 2-amino-5-(2-hydroxy) One or more of the following: (Ethyl)-4(3H)-pyrimidinone, polyether polyol, polyester polyol, polybutane glycol, polytetramethylene ether diol, polytetrahydrofurfuryl alcohol, polycaprolactone polyol, polylactic acid polyol, polycarbonate polyol, polyamide polyol, polysiloxane polyol, polyacrylate polyol, polysulfone polyol, polyisobutylene polyol, polystyrene polyol, polyurethane polyol, polyisocyanate polyol, polyesteramide polyol, and polyepoxy resin polyol;

[0048] Molecules containing R6 and R7 are selected from polyols containing R5, polyols with zwitterionic or zwitterionic precursor groups, alcohols, amines, carboxylic acids, and CH3(CH2). w OH, methanol, ethanol, propanol, isopropanol, isobutanol, butanol, hexanol, pentanol, alkyl alcohols, aromatic alcohols, CH3(CH2) uNH2, methylamine, ethylamine, propylamine, isopropylamine, isobutylamine, butylamine, hexylamine, pentanamine, alkylamine, aromatic amine, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 6-hydroxyhexyl acrylate, glyceryl acrylate, glyceryl methacrylate, 4-hydroxyphenyl acrylate, 4-hydroxyphenyl methacrylate, 3-(N,N-dimethylamino)propyl acrylate, 3-(N,N-dimethylamino)propyl methacrylate, hydroxyl-terminated polyethylene glycol acrylate, hydroxyl-terminated polyethylene glycol methacrylate, polyethylene glycol diacrylate - bifunctional monomer, polyethylene glycol dimethacrylate - bifunctional monomer, hydroxyl-terminated polypropylene glycol acrylate, hydroxyl-terminated polypropylene glycol methacrylate, hydroxyl-terminated polytetramethylene ether glycol diacrylate, hydroxyl-terminated polytetramethylene ether glycol diacrylate Ether glycol dimethacrylate, hydroxyl-containing polyurethane acrylate, hydroxyl-containing polyester acrylate, hydroxyl-terminated polyester methacrylate, hydroxyl-containing polyether acrylate, hydroxyl-terminated polyether methacrylate, 2-hydroxy-3-propyl acrylate, 2-hydroxy-3-butyl acrylate, 2-hydroxy-3-methylbutyl acrylate, 2-hydroxyethyl-2-methylpropyl acrylate, 2-hydroxyethyl-3-methylbutyl acrylate, 2-hydroxyethyl-4-methylpentyl acrylate, 3-hydroxy-3-methylbutyl methacrylate, tetraphenylvinyl alcohol, 9,10-dihydroxyanthracene, 2-hydroxy-1,8-naphthalimide, 9-hydroxyfluorenone, hydroxycoumarin hydroxy derivatives, hydroxyl-containing fluorescein (such as 5,6-dihydroxyfluorescein), hydroxyl-containing porphyrin derivatives, hydroxyl-containing benzothiazole and benzimidazole derivatives, hydroxyl-containing stilbene derivatives, and hydroxyl-containing polystyrene derivatives, one or more of these.

[0049] Where m, r, o, p, v, t, w, and u are independent integers selected from 1 to 1000;

[0050] The polymer molecular weight ranges from 1,000 to 1,000,000 g / mol.

[0051] The zwitterionic polyurethane provided by this invention has paired cations and anions in the repeating unit, and the polymer is electrically neutral as a whole. Due to the presence of zwitterionic groups, a dense hydration layer is formed on the surface of the polymer material, thereby enabling the polymer to resist non-specific protein adsorption.

[0052] In one embodiment of the present invention, preferably, the molecular structure of the zwitterionic polyurethane is selected from one of the following:

[0053]

[0054] Where m, n, o, x, y, and z are independent integers selected from 1 to 1000.

[0055] The present invention further provides a method for preparing the zwitterionic polyurethane, comprising the following steps:

[0056] An intermediate polymer is obtained by polymerizing zwitterionic precursor diol, polyisocyanate, and polyol. Subsequently, the side chains of the intermediate polymer are removed to obtain the zwitterionic polyurethane.

[0057] The zwitterionic precursor diol is selected from the following structures:

[0058]

[0059] The polyisocyanate is selected from the following structures:

[0060] The polyol is selected from one of the following structures: R7-(OH) p ;

[0061] The intermediate polymer is selected from one of the following structures:

[0062]

[0063] The selection of R1-R9, m, n, o, p, v, and t is the same as that of the zwitterionic polyurethane. Preferably, R1 is selected from -(CH2)2- or -(CH2)3-; R2 is selected from -(CH2)2- and -(CH2)3-; R3 is selected from -CH2- and -(CH2)2-; R4 is selected from -O-; R5 is selected from -H, -CH3, -CH2CH3, and -C(CH3)3; R6 is selected from hexamethylene diisocyanate, isophorone diisocyanate, and dicyclohexylmethane diisocyanate; R7 is selected from ethylene glycol (EG), propylene glycol (PG), 1,3-propanediol, 1,4-butanediol, polybutanediol, polycarbonate polyol, polytetramethylene ether glycol, and polyester polyol; and molecules containing R8 and R9 are selected from methanol, ethanol, propanol, isopropanol, isobutanol, butanol, hexanol, pentanol, alkyl alcohols, aromatic alcohols, methylamine, ethylamine, propylamine, isopropylamine, isobutylamine, butylamine, hexamine, pentanol, alkylamine, and aromatic amines.

[0064] The present invention further provides a method for preparing the zwitterionic polyurethane, comprising the following steps:

[0065] An intermediate polymer is obtained by polymerizing zwitterionic precursor diol and polyisocyanate, followed by removal of the side chains of the intermediate polymer to obtain the zwitterionic polyurethane.

[0066] The zwitterionic precursor diol is selected from the following structures:

[0067]

[0068] The polyisocyanate is selected from the following structures:

[0069] The intermediate polymer is selected from one of the following structures:

[0070]

[0071] The selection of R1-R8, m, n, o, p, v, t, w, and u is the same as that of the zwitterionic polyurethane.

[0072] In one embodiment of the present invention, the preparation route of the zwitterionic polyurethane is selected from one of the following:

[0073]

[0074]

[0075] In one embodiment of the present invention, the preparation route of the zwitterionic polyurethane is selected from one of the following:

[0076]

[0077]

[0078] A method for preparing zwitterionic polyurethane includes the following steps:

[0079] The zwitterionic polyurethane is obtained by polymerization of zwitterionic diols, polyols, and polyisocyanates, wherein...

[0080] The zwitterionic diol is selected from the following structures:

[0081]

[0082] The zwitterionic precursor diol is selected from the following structure: R7-(OH) p

[0083] The polyisocyanate is selected from the following structures:

[0084]

[0085] The zwitterionic polyurethane is selected from one of the following structures:

[0086]

[0087] Where x, y, and n are integers selected from 1 to 1000.

[0088] R1 is selected from -(CH2)2-, -(CH2)3-, and -(CH2). r -、-(CH2) n O(CH2) s -、-(CH2CH2OCH2CH2) t -, -CH2CH2(OCH2CH2) u - one or more of them;

[0089] R2 is selected from -(CH2)2-, -(CH2)3-, and -(CH2). r -、-(CH2) n O(CH2) s -、-(CH2CH2OCH2CH2) t -, -CH2CH2(OCH2CH2) u - one or more of them;

[0090] R3 is selected from -CH2-, -(CH2)2-, and -(CH2). r -、-(CH2) n O(CH2) s -、-(CH2CH2OCH2CH2) t -, -CH2CH2(OCH2CH2) u - one or more of them;

[0091] R4 is selected from -O-, -NH-, or -S-.

[0092] R5 is selected from -H, -CH3, and -(CH2). v One or more of the following: CH3, -C(CH3)3, alkyl, alkenyl, alkynyl, polyester, polyether, polyamide, monosaccharide, oligosaccharide, polysaccharide or glycoside;

[0093] The polyisocyanate containing R6 is selected from one or more of the following: toluene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, dicyclohexylmethane diisocyanate, naphthalene diisocyanate, isophthalimethylene diisocyanate, terephthalimethylene diisocyanate, cyclohexyldimethyl diisocyanate, isosorbide diisocyanate, ethylene glycol diisocyanate, triphenylmethane triisocyanate, propylene glycol diisocyanate, and bis(2-isocyanate ethyl) sulfide.

[0094] The polyols containing R7 are selected from ethylene glycol (EG), propylene glycol (PG), 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol (BDO), neopentyl glycol (NPG), 1,2,3-propanetriol (glycerol), 1,2,3-butanetriol, 1,2,6-hexanetriol, glycerol (glycerol), erythritol, sorbitol, and mannitol. Xylitol, polyether polyol, polyester polyol, polybutane glycol, polytetramethylene ether glycol (PTMEG), polytetrahydrofurfuryl alcohol, polycaprolactone polyol, polylactic acid polyol, polycarbonate polyol, polyamide polyol, polysiloxane polyol, polyacrylate polyol, polysulfone polyol, polyisobutylene polyol, polystyrene polyol, polyurethane polyol, polyisocyanate polyol, polyesteramide polyol, and one or more of epoxy resin polyols;

[0095] Molecules containing R8 and R9 are selected from polyols containing R7, polyols with zwitterionic or zwitterionic precursor groups, amines, carboxylic acids, and CH3(CH2). w OH, methanol, ethanol, propanol, isopropanol, isobutanol, butanol, hexanol, pentanol, alkyl alcohols, aromatic alcohols, CH3(CH2) xNH2, methylamine, ethylamine, propylamine, isopropylamine, isobutylamine, butylamine, hexylamine, pentanamine, alkylamine, aromatic amine, dihydroxy polyethylene glycol, dihydroxy polytetrahydrofuran, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 6-hydroxyhexyl acrylate, glyceryl acrylate, glyceryl methacrylate, 4-hydroxyphenyl acrylate, 4-hydroxyphenyl methacrylate, 3-(N,N-dimethylamino)propyl acrylate, 3-(N,N-dimethylamino)propyl methacrylate, hydroxyl-terminated polyethylene glycol acrylate, hydroxyl-terminated polyethylene glycol methacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, hydroxyl-terminated polypropylene glycol acrylate, hydroxyl-terminated polypropylene glycol methacrylate, hydroxyl-terminated polytetramethylene ether glycol diacrylate, hydroxyl-terminated polytetramethylene ether glycol diacrylate Methyl ether glycol dimethacrylate, hydroxyl-containing polyurethane acrylate, hydroxyl-containing polyester acrylate, hydroxyl-terminated polyester methacrylate, hydroxyl-containing polyether acrylate, hydroxyl-terminated polyether methacrylate, 2-hydroxy-3-propyl acrylate, 2-hydroxy-3-butyl acrylate, 2-hydroxy-3-methylbutyl acrylate, 2-hydroxyethyl-2-methylpropyl acrylate, 2-hydroxyethyl-3-methylbutyl acrylate, 2-hydroxyethyl-4-methylpentyl acrylate, 3-hydroxy-3-methylbutyl methacrylate, tetraphenylvinyl alcohol, 9,10-dihydroxyanthracene, 2-hydroxy-1,8-naphthylimide, 9-hydroxyfluorenone, hydroxyl coumarin derivatives, hydroxyl-containing fluorescein (such as 5,6-dihydroxyfluorescein), hydroxyl-containing porphyrin derivatives, hydroxyl-containing benzothiazole and benzimidazole derivatives, hydroxyl-containing stilbene derivatives, and hydroxyl-containing polystyrene derivatives, one or more of these.

[0096] R 10 Selected from H-, CH3-, CH3CH2-, CH3(CH2) y -, CH3O-(CH2CH2O) z CH2CH2-, one or more of the following: ethyl bromoacetate, methyl bromoacetate, alkyl bromoacetate, tert-butyl bromopropionate, methyl bromopropionate, tert-butyl bromopropionate, alkyl bromopropionate, tert-butyl bromobutyrate, methyl bromobutyrate, tert-butyl bromobutyrate, and alkyl bromobutyrate.

[0097] A - Selected from F - Cl - ,Br - I - SO4 2- NO3 - CO3 2- PO4 3-SiO3 2- ClO4 - CrO4 2- PF6 - BF4 - CF3SO3 - SiF6 2- CN - SCN - OCN - HCOO - CH3COO - C2O4 2- C6H5O7 3- C6H5COO - CF3COO - CF3SO3 - N(CF3SO2)2 2- One or more organic or inorganic anions;

[0098] M + Independently selected from Li + Na + K + Ca 2+ Mg 2+ Fe 2+ Fe 3+ Zn 2+ Inorganic metal cations, or one or more organic cations selected from quaternary ammonium cations, phosphonium cations, etc.;

[0099] Where m, n, o, r, s, t, u, v, w, x, y, z are independent integers selected from 1 to 1000.

[0100] The polymer has a molecular weight of approximately 1,000 to approximately 1,000,000 g / mol.

[0101] The present invention further provides the application of the zwitterionic polyurethane in the preparation of medical devices, active pharmaceutical ingredients, drug carriers or biomaterials.

[0102] In one embodiment of the present invention, the medical device includes, but is not limited to, interventional devices, implants, extracorporeal circulation devices, or in vitro diagnostic devices.

[0103] In one embodiment of the present invention, the interventional device or implant is a medical catheter, artificial blood vessel, vascular stent, valve, patch, dressing, or biosensor.

[0104] In one embodiment of the present invention, the application includes blending the zwitterionic polyurethane or its precursor as a toughening agent or antifouling modifier with a polymeric material to prepare the medical device, drug carrier or biomaterial.

[0105] In one embodiment of the present invention, the application includes blending the zwitterionic polyurethane or its precursor as a toughening agent or antifouling modifier with a polymeric material to prepare the medical device, drug carrier or biomaterial.

[0106] In one embodiment of the present invention, the drug carrier is a microsphere, nanoparticle, fiber, or hydrogel based on the zwitterionic polyurethane or its precursor.

[0107] In one embodiment of the present invention, the biomaterial includes tissue engineering scaffolds or medical aesthetic filler materials.

[0108] In one embodiment of the invention, a dressing or tissue repair scaffold that promotes wound healing is made of a zwitterionic precursor; the wound includes a chronic wound, a traumatic wound, or a burn wound.

[0109] In one embodiment of the invention, the chronic wound is a diabetic foot ulcer or pressure sore.

[0110] In one embodiment of the present invention, the zwitterionic polyurethane, the zwitterionic polyurethane precursor prepared by the method, and the product are wound dressings, artificial skin, scar-inhibiting gels, or tissue adhesives.

[0111] In one embodiment of the present invention, an anti-biofouling product is provided, which is a zwitterionic polyurethane or a zwitterionic polyurethane precursor prepared by the method; the product is a medical device, a water treatment membrane, a food industry equipment, a household hygiene product, a marine equipment protective structure, an industrial pipeline, a heat exchanger, or a functional textile.

[0112] In one embodiment of the present invention, the biofouling includes at least one of the following: organic molecule adsorption, biomolecule adsorption, protein adsorption, bacterial adhesion, fungal adhesion, viral adhesion, biofilm formation, thrombosis, foreign body reaction, biocalcification, algal attachment, or marine organism attachment.

[0113] In one embodiment of the present invention, the zwitterionic polyurethane, the zwitterionic polyurethane precursor prepared by the method, is used to suppress non-specific adsorption of biomolecules or organisms.

[0114] In one embodiment of the present invention, the zwitterionic polyurethane, the zwitterionic polyurethane precursor prepared by the method, and the pharmaceutically acceptable carrier, industrial polymer matrix, or coating solvent are included.

[0115] In one embodiment of the present invention, the zwitterionic polyurethane, or the zwitterionic polyurethane precursor prepared by the method, is applied to the surface of a substrate or product by means of coating, blending, impregnation or molding.

[0116] In one embodiment of the present invention, the application of the zwitterionic polyurethane in the preparation of medical devices further includes using the zwitterionic polyurethane as a toughening material, blending it with most polymers used in medical devices, and then preparing the medical device.

[0117] In one embodiment of the present invention, the drug carrier refers to the preparation of the zwitterionic polyurethane into biodegradable zwitterionic polyurethane microspheres for drug delivery.

[0118] In one embodiment of the present invention, the biomaterial includes medical aesthetic materials, such as medical aesthetic fillers.

[0119] This application provides a method for preparing and applying polyurethane. First, an amphoteric precursor diol containing ester bonds is prepared, which is then polymerized with a polyisocyanate to obtain polyurethane, using monomers with single-terminated amino or hydroxyl groups for end-capping. Finally, the amphoteric polyurethane is obtained through ester bond cleavage. The amphoteric polyurethane prepared in this application has controllable mechanical properties and can be used to prepare medical devices or healthcare products, such as medical catheters, valves, repair patches, vascular stents, dressings, and biosensors, through traditional processing methods such as extrusion and injection molding, as well as photocuring. It can also be used to prepare biodegradable amphoteric polyurethane microspheres for drug delivery or cosmetic fillers. Furthermore, it can be used as a toughening agent in blending with most polymers used in medical devices without phase separation. The amphoteric groups endow the polyurethane with excellent biocompatibility, anti-protein adsorption, anti-cell adhesion, long-term anti-rejection, anti-thrombotic, and anti-biofilm properties.

[0120] The amphoteric polyurethane and its precursor materials obtained in this invention have tunable mechanical properties and support processing methods such as extrusion, injection molding, and photopolymerization. They are suitable for medical devices, drug delivery carriers, cosmetic fillers, and industrial and civilian antifouling applications. The zwitterionic structure endows them with excellent properties such as anti-protein adsorption, anti-cell adhesion, anti-biofilm formation, antioxidant properties, and wound healing promotion. They can be widely used in medical catheters, artificial blood vessels, water treatment filter membranes, marine antifouling coatings, food processing equipment, household bathroom fixtures, air conditioning systems, and industrial pipeline protection. This polyurethane can also be blended with various polymers as a toughening agent, exhibiting good compatibility and no phase separation.

[0121] Compared with the prior art, the present invention has the following advantages and beneficial effects:

[0122] The zwitterionic polyurethane provided by this invention can resist long-term adsorption of proteins, platelets, cells, and bacteria, exhibiting excellent biocompatibility. It can be processed into medical devices using traditional methods. Furthermore, biodegradable components can be introduced to prepare microspheres, which can be used for drug delivery and cosmetic fillers.

[0123] The zwitterionic polyurethane provided by this invention has tunable mechanical properties, and the polymerization system is compatible with a large number of functional monomers, thereby introducing photocurable and luminescent properties for use in tissue engineering reconstruction and detection in medicine. Attached Figure Description

[0124] Figure 1 The synthetic route for poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethane (PDPAEG-PTHF) in Example 2 is as follows;

[0125] Figure 2 The GPC spectrum of poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethane (PDPAEG-PTHF) in Example 2 is shown below.

[0126] Figure 3 The images show the infrared spectra of poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethane (PDPAEG-PTHF) before and after irradiation (a). in Example 2.

[0127] Figure 4 The figures show the compressive stress-strain curves of poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethane (PDPAEG-PTHF) before and after hydrolysis (a) in Example 2.

[0128] Figure 5 The hemolysis rate of poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethane (PDPAEG-PTHF) in Example 2;

[0129] Figure 6 This is a fluorescence image of proteins adsorbed on the surface of poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethane (PDPAEG-PTHF) in Example 2;

[0130] Figure 7 The image shows the fluorescence of platelets adsorbed on the surface of poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethane (PDPAEG-PTHF) in Example 2.

[0131] Figure 8 The image shows the fluorescence of L929 cells adsorbed on the surface of poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethane (PDPAEG-PTHF) in Example 2.

[0132] Figure 9 This is a fluorescence image of Escherichia coli adsorbed on the surface of poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethane (PDPAEG-PTHF) in Example 2;

[0133] Figure 10 The images show fluorescence images of Staphylococcus epidermidis, Pseudomonas aeruginosa, and Candida albicans adsorbed on the surface of poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethane (PDPAEG-PTHF) in Example 2. Also shown are HE-stained images of skin tissue implanted subcutaneously in rats after incubation with polyurethane and Staphylococcus aureus.

[0134] Figure 11 These are HE and M&T stained images of skin tissue sections from mice two and four months after implantation of poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethane (PDPAEG-PTHF) in Example 2.

[0135] Figure 12 These are HE and M&T stained images of skin tissue sections from cynomolgus monkeys three months after the poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethane (PDPAEG-PTHF) was implanted in the monkeys in Example 2.

[0136] Figure 13 This is a photograph of PDPAEG-PTHF-100 extruded into a conduit in Example 2;

[0137] Figure 14 To demonstrate the free radical scavenging properties of polyurethane in Example 2, PCBDA is a carboxybetaine hydrogel;

[0138] Figure 15 Polyurethane was used as a dressing for wound repair in mice in Example 2;

[0139] Figure 16 Polyurethane was used as a dressing for wound repair in diabetic rats in Example 2;

[0140] Figure 17 This is the synthetic route for the zwitterionic polyurethane (poly(dihydroxypropylglycine methyl ester-glycerol-polytetrahydrofuran)) precursor in Example 3.

[0141] Figure 18 This is the synthetic route for the zwitterionic polyurethane (poly(dihydroxypropylglycine ethyl ester-polycaprolactone)) precursor in Example 4.

[0142] Figure 19 Photographs of polyurethane (poly(dihydroxypropylglycine ethyl ester-polycaprolactone)) microspheres from Example 4. a. Micrographs of polymer microspheres prepared in three different dispersed phases. b. Scanning electron microscope image of microspheres prepared in Tween 20.

[0143] Figure 20 This is the synthetic route for the zwitterionic polyurethane (poly(dihydroxypropylglycine methyl ester-furan-bismaleimide-polytetrahydrofuran)) precursor in Example 5.

[0144] Figure 21 This is the synthetic route for the zwitterionic polyurethane (poly(dihydroxypropylglycine methyl ester-furan-ureidopyrimidinone-bismaleimide-polytetrahydrofuran)) precursor in Example 6.

[0145] Figure 22 This is the synthetic route for the zwitterionic polyurethane (poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran-hydroxyethyl methacrylate)) precursor in Example 7.

[0146] Figure 23 This is the synthetic route for the zwitterionic polyurethane (poly(dihydroxypropylglycine methyl ester-polycarbonate-polydimethylsiloxane) precursor in Example 8.

[0147] Figure 24 In Example 8, zwitterionic polyurethane (poly(dihydroxypropylglycine methyl ester-polycarbonate-polydimethylsiloxane) was used as an abdominal wall hernia repair patch. Detailed Implementation

[0148] The present invention will now be described in detail with reference to the accompanying drawings and specific embodiments.

[0149] The general experimental methods described in the following examples are as follows:

[0150] Analysis of infrared spectra:

[0151] The chemical structure of polyurethane was analyzed using a Fourier transform infrared microscopy (Nicoleti S50) in total reflectance mode. Each sample was analyzed at 400-4000 cm⁻¹. -1 The range was scanned 32 times, with a spectral resolution of 2 cm⁻¹. -1 .

[0152] Determination of the mechanical properties of zwitterionic polyurethane materials:

[0153] The material to be tested (polyurethane material) is cut into discs with a diameter of 10 mm and a thickness of 1.5-2 mm. The polyurethane discs are then compressed at a rate of 1 mm / min until failure, with a maximum loading force of 900 N.

[0154] Animal experiments were conducted as follows:

[0155] Polyurethane discs with a diameter of 8 mm and a thickness of 1-2 mm (hydrolyzed for approximately 4 days) were implanted subcutaneously into the back of mice. Two months after implantation, the tissue was excised, embedded, sectioned, and stained with Masson's trichrome (M&T).

[0156] Experiment on resistance to protein adsorption:

[0157] First, fibrinogen (250 mg) was dissolved in 5 mL of Na₂CO₃ (pH = 9–10). Rhodamine B dissolved in a small amount of DMSO was added under ice bath conditions, and the reaction was allowed to proceed for 20 h. After adding ammonium chloride, the reaction was stopped, and free dye was removed using an Akta protein purification system (AKTA Pure25). The hydrolyzed polyurethane discs (8 mm in diameter) were placed in a 24-well plate. 1 mL of Rhodamine B-labeled fibrinogen (1 mg / mL, in PBS) was added to each well to cover the sample. The plate was incubated at 37 °C for 3 h. Then, the solution in each well was discarded, 1 mL of deionized water was added, the plate was shaken for 30 seconds, and the solution in each well was discarded again. This washing process was repeated five times. The polyurethane disc samples were removed, and the surface moisture was blotted dry with Kimwipes. Fibrinogen adsorption on the surface was observed using a confocal microscope (LSM900).

[0158] Anti-cell adhesion experiment:

[0159] After hydrolysis, the polyurethane discs (8 mm in diameter) to be tested were equilibrated in PBS for 24 h, then placed in 24-well plates and cultured in serum medium consisting of DMEM, 10% fetal bovine serum (FBS), and 1% penicillin-streptomycin at a concentration of 2 × 10⁻⁶ mg / well. 5 L929 cells were seeded at a concentration of [number] cells and cultured at 37°C in a 5% CO2 incubator for 24 h. The culture medium was discarded, and the cells were washed three times with PBS. 1 mL of fresh culture medium containing Hoechst 33342 (10 μg / mL) was added to stain the cells for 30 min. The cells were gently washed twice with PBS, fixed with paraformaldehyde, and the cell surface coverage was observed using a confocal microscope (LSM900).

[0160] Anti-Escherichia coli adhesion test:

[0161] Transfer 1 mL of E. coli culture to a 24-well plate. Each well has a sample tray (8 mm in diameter) at the bottom. After 24 hours of incubation, collect the sample to be tested (the polyurethane to be tested) using sterile forceps and gently rinse three times with deionized water. Add 100 μL of the sample to the plate. BacLight TM The staining solution was added to the sample surface and incubated for 10 minutes. The sample was then removed with sterile forceps and gently rinsed three times in deionized water. The surface coverage of *E. coli* was observed using a confocal microscope (LSM900).

[0162] Antiplatelet adhesion test:

[0163] The test material (polyurethane material) was immersed in fetal bovine serum for 3 and 6 weeks, respectively. After removing the serum, the material was washed with PBS. Rabbit whole blood was centrifuged at 180g for 10 min, and the supernatant was collected to obtain platelet-rich plasma (PRP). 100 μL of undiluted PRP was added to the material and incubated for 3 days, 1 week, and 2 weeks. Fresh PRP was added daily. Excess liquid was discarded, and the material was washed with 200 μL of PBS three times. The material was fixed with 4% paraformaldehyde at room temperature for 30 min. After fixation, excess liquid was discarded, and the material was washed twice with 200 μL of PBS containing 0.1% TritionX-100, each time for 5 min. After washing, the dressing was protected from light and stained with 200 μL of staining working solution (alFluo594-labeled phalloidin) at room temperature for 1 hour. The surface liquid was aspirated, and platelets adhering to the dressing surface were observed using laser confocal microscopy (LSM900).

[0164] Example 1

[0165] Synthesis of zwitterionic polyurethane (ethyl (2-dihydroxypropylamine)-polytetrahydrofuran)

[0166] Dihydroxypropylamine (10 g, 0.075 mol) and ethyl bromoacetate (12.66 g, 0.076 mol) were added to acetonitrile and reacted at 60 °C for 12 h. The product was precipitated in diethyl ether and dried under vacuum overnight to give ethyl (2-dihydroxypropylamine)acetate.

[0167] Experiment 1: Ethyl (2-dihydroxypropylamine)ethyl acetate (15 g, 0.0684 mol) and polytetrahydrofuran (7.6 g, 0.0076 mol) were added to a nitrogen-purged three-necked flask. Isophorone diisocyanate (IPDI, 16.9 g, 0.076 mol) was then added, and the reaction was carried out at 60 °C. Acetone was added in 10 mL increments as the viscosity increased. After 2 days of reaction, anhydrous ethanol was added, and the reaction was continued for another 2 hours. The resulting polyurethane was precipitated three times in diethyl ether and dried under vacuum to remove the solvent. The molecular weight of the obtained polyurethane was 20359 g / mol. The polyurethane was redissolved in acetone, and the resulting polymer solution was poured into a PTFE mold. After drying, the resulting polyurethane film was immersed in water for one week to obtain zwitterionic polyurethane.

[0168] Experiment 2: Ethyl (2-dihydroxypropylamine)ethyl acetate (15 g, 0.0684 mol) and polytetrahydrofuran (7.6 g, 0.0076 mol) were added to a three-necked flask purged with nitrogen. Isophorone diisocyanate (IPDI, 8.45 g, 0.038 mol) and hexamethylene diisocyanate (HDI, structural reference) were then added. Figure 1(6.39 g, 0.038 mol) was reacted at 60 °C. Acetone was added in 10 mL increments as viscosity increased. After 2 days of reaction, anhydrous ethanol was added to continue the reaction for another 2 hours. The resulting polyurethane was precipitated three times in diethyl ether and dried under vacuum to remove the solvent. The molecular weight of the obtained polyurethane was 31312 g / mol. The polyurethane was redissolved in acetone, and the resulting polymer solution was poured into a PTFE mold. After drying, the resulting polyurethane film was immersed in water for one week to obtain zwitterionic polyurethane.

[0169] Experiment 3: Ethyl (2-dihydroxypropylamine)ethyl acetate (15 g, 0.0684 mol) and polytetrahydrofuran (7.6 g, 0.0076 mol) were added to a three-necked flask purged with nitrogen. Dicyclohexylmethane diisocyanate (HMDI, 22.16 g, 0.076 mol) was then added, and the reaction was carried out at 60 °C. Acetone was added in 10 mL increments as the viscosity increased. After 2 days of reaction, anhydrous ethanol was added, and the reaction continued for another 2 hours. The resulting polyurethane was precipitated three times in diethyl ether and dried under vacuum to remove the solvent. The molecular weight of the obtained polyurethane was 8765 g / mol. The polyurethane was redissolved in acetone, and the resulting polymer solution was poured into a PTFE mold. After drying, the resulting polyurethane film was immersed in water for one week to obtain zwitterionic polyurethane.

[0170] Experiment 4: Ethyl (2-dihydroxypropylamine)ethyl acetate (15 g, 0.0684 mol) and polytetrahydrofuran (17.1 g, 0.017 mol) were added to a nitrogen-purged three-necked flask. Isophorone diisocyanate (IPDI, 19.01 g, 0.0855 mol) was then added, and the reaction was carried out at 60 °C. Acetone was added in 10 mL increments as the viscosity increased. After 2 days of reaction, anhydrous ethanol was added, and the reaction was continued for another 2 hours. The resulting polyurethane was precipitated three times in diethyl ether and dried under vacuum to remove the solvent. The molecular weight of the obtained polyurethane was 18315 g / mol. The polyurethane was redissolved in acetone, and the resulting polymer solution was poured into a PTFE mold. After drying, the resulting polyurethane film was immersed in water for one week to obtain zwitterionic polyurethane.

[0171] The common feature of the different experiments in this embodiment is that they all involve the reaction of ethyl acetate (2-dihydroxypropylamine), polytetrahydrofuran, and diisocyanate; the difference is that different diisocyanates are used in the different experiments.

[0172] The molecular weights of the polymers obtained in this embodiment are shown in Table 1.

[0173] Table 1. Molecular weights of polymers obtained from different experiments in Example 1.

[0174]

[0175] Example 2

[0176] Synthesis of zwitterionic polyurethane (poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethane, PDPAEG-PTHF)

[0177] Glycine methyl ester, potassium bicarbonate, and potassium iodide were dispersed in 2 L of acetonitrile and added to a three-necked flask. The mixture was stirred thoroughly and heated to 60 °C. During heating, the hydrochloride and potassium bicarbonate neutralized, gradually producing bubbles. Liquid reflux occurred at the lower end of the bulb cooler, and 0.5 L of bromopropanol in acetonitrile was slowly added dropwise. After reflux for 24 h, the upper end of the bulb cooler was covered with a perforated plastic wrap to prevent liquid splashing and the entry of external moisture. The reaction was stopped after 48 h, and excess potassium salt was removed by filtration. The filtrate was evaporated to dryness and then redissolved in DCM, producing a white precipitate. The supernatant was centrifuged, and the supernatant was evaporated to dryness. This process was repeated 2-3 times until no precipitate was formed upon addition of DCM. Evaporation yielded 120 g of a yellow oily liquid, which was the crude DPAEG product. The product was purified by column chromatography using a solvent (dichloromethane:methanol = 10:1) to obtain nearly colorless and transparent DPAEG. (DPAEG structure reference) Figure 1 .

[0178] Experiment 1: Polytetrahydrofuran (PTHF, structural reference) Figure 1 22.27 g (0.0223 mol) and HDI (3.7456 g, 0.0223 mol) were sequentially added to a nitrogen-purged three-necked flask and reacted at 60 °C. Acetone was added in 5 mL increments as viscosity increased. After 3 days of reaction, anhydrous ethanol was added to continue the reaction for 2 hours. The resulting polyurethane was precipitated three times in diethyl ether and dried under vacuum to remove the solvent. The molecular weight of the obtained polyurethane was 49810 g / mol. The polyurethane was redissolved in acetone, and the resulting polymer solution was poured into a PTFE mold. After drying, the resulting polyurethane membrane was immersed in PBS buffer for 5 days to obtain zwitterionic polyurethane.

[0179] Experiment 2: DPAEG (1.5 g, 0.0073 mol) and polytetrahydrofuran (21.94 g, 0.022 mol) were sequentially added to a nitrogen-purged three-necked flask, followed by the addition of HDI (4.88 g, 0.029 mol), and the reaction was carried out at 60 °C. Acetone was added in 5 mL increments as the viscosity increased. After 3 days of reaction, anhydrous ethanol was added, and the reaction continued for 2 hours. The resulting polyurethane was precipitated three times in diethyl ether, and the solvent was removed by vacuum drying. The molecular weight of the obtained polyurethane was 47738 g / mol. The polyurethane was redissolved in acetone, and the resulting polymer solution was poured into a PTFE mold. After drying, the resulting polyurethane membrane was immersed in PBS buffer for 5 days to obtain zwitterionic polyurethane.

[0180] Experiment 3: DPAEG (2.12 g, 0.01034 mol) and polytetrahydrofuran (10.34 g, 0.01034 mol) were added sequentially to a nitrogen-purged three-necked flask, followed by the addition of HDI (3.48 g, 0.02068 mol), and the reaction was carried out at 60 °C. Acetone was added in 5 mL increments as the viscosity increased. After 3 days of reaction, anhydrous ethanol was added, and the reaction continued for 2 hours. The resulting polyurethane was precipitated three times in diethyl ether, and the solvent was removed by vacuum drying. The molecular weight of the obtained polyurethane was 51053 g / mol. The polyurethane was redissolved in acetone, and the resulting polymer solution was poured into a PTFE mold. After drying, the resulting polyurethane membrane was immersed in PBS buffer for 5 days to obtain zwitterionic polyurethane.

[0181] Experiment 4: DPAEG (13.6 g, 0.0663 mol) and polytetrahydrofuran (22.1 g, 0.0221 mol) were added sequentially to a nitrogen-purged three-necked flask, followed by the addition of HDI (15.02 g, 0.0884 mol), and the reaction was carried out at 60 °C. Acetone was added in 5 mL increments as the viscosity increased. After 3 days of reaction, anhydrous ethanol was added, and the reaction was continued for another 2 hours. The resulting polyurethane was precipitated three times in diethyl ether and dried under vacuum to remove the solvent. The molecular weight of the obtained polyurethane was 53347 g / mol. The polyurethane was redissolved in acetone, and the resulting polymer solution was poured into a PTFE mold. After drying, the resulting polyurethane membrane was immersed in PBS buffer for 5 days to obtain zwitterionic polyurethane.

[0182] Experiment 5: DPAEG (20.54 g, 0.1 mol) and HDI (16.82 g, 0.1 mol) were added to a nitrogen-purged three-necked flask and reacted at 60 °C. Acetone was added in 5 mL increments as the viscosity increased. After 3 days of reaction, anhydrous ethanol was added to continue the reaction for 2 hours. The resulting polyurethane was precipitated three times in diethyl ether and dried under vacuum to remove the solvent. The molecular weight of the obtained polyurethane was 63852 g / mol. The polyurethane was redissolved in acetone, and the resulting polymer solution was poured into a PTFE mold. After drying, the resulting polyurethane membrane was immersed in PBS buffer for 5 days to obtain zwitterionic polyurethane.

[0183] Figure 1 This document presents the synthetic routes for poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethanes obtained in different experiments within this embodiment. The difference between the experiments lies in the varying feed ratios of DPAEG, HDI, and PTHF. The five polyurethanes obtained from the above experiments are named PDPAEG-PTHF-0, PDPAEG-PTHF-25, PDPAEG-PTHF-50, PDPAEG-PTHF-75, and PDPAEG-PTHF-100, and their structures are referenced from [reference needed]. Figure 1 In the naming of the five polyurethanes obtained from five different experiments, the numbers following them indicate the differences in DPAEG content.

[0184] The GPC spectra of poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethane (PDPAEG-PTHF) (i.e., PDPAEG-PTHF-0, PDPAEG-PTHF-25, PDPAEG-PTHF-50, PDPAEG-PTHF-75, PDPAEG-PTHF-100) in Example 2 are as follows: Figure 2 As shown, from Figure 2 It can be seen that even without the use of toxic metal catalysts, the molecular weight can reach approximately 50,000 to 60,000 g / mol.

[0185] In Example 2, the infrared spectra of poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethane (PDPAEG-PTHF) (i.e., PDPAEG-PTHF-0, PDPAEG-PTHF-25, PDPAEG-PTHF-50, PDPAEG-PTHF-75, PDPAEG-PTHF-100) before and after irradiation (a.) are as follows: Figure 3 As shown, from Figure 3 The infrared spectrum shows that all isocyanate groups have reacted completely, and all prepared polyurethanes can withstand 30 kGy of irradiation sterilization.

[0186] The compressive stress-strain curves of poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethane (PDPAEG-PTHF) (i.e., PDPAEG-PTHF-0, PDPAEG-PTHF-25, PDPAEG-PTHF-50, PDPAEG-PTHF-75, PDPAEG-PTHF-100) before and after hydrolysis (a.) in Example 2 are shown below. Figure 4 As shown. From Figure 4 Compression test results showed that PDPAEG-PTHFs did not fail under maximum stress, and the mechanical properties of polyurethane could be controlled by adjusting the feed ratio of PDPAEG and polytetrahydrofuran.

[0187] In Example 2, the hemolysis rate of poly(dihydroxypropyl glycine methyl ester-polytetrahydrofuran) polyurethane (PDPAEG-PTHF) (i.e., PDPAEG-PTHF-0, PDPAEG-PTHF-25, PDPAEG-PTHF-50, PDPAEG-PTHF-75, PDPAEG-PTHF-100) was as follows: Figure 5 As shown.

[0188] Figure 5 The study also included Triton X-100 (polyethylene glycol octylphenyl ether) and EG-85A (TPU (thermoplastic polyurethane) 9392AGMPEG-85A) as comparative examples.

[0189] Figure 5 The method for testing hemolysis rate was as follows: Rabbit whole blood was collected using blood collection tubes, centrifuged at 1500g for 15 minutes, and washed with physiological saline. The resulting blood cells were diluted 10-fold with 1×PBS to prepare a working solution. Materials (0.5×0.5cm) 2 Place the sample in a 24-well plate, add 1 mL of working solution, and incubate at 37°C for 3 hours. After incubation, centrifuge and use the supernatant for detection. Add 100 μL of supernatant to a 96-well plate and measure the absorbance at 545 nm using a microplate reader. In this experiment, the group containing 2% Triton X-100 was the positive control, and physiological saline was the negative control. The hemolysis rate was calculated using the following formula.

[0190]

[0191] Where As, An, and Ap are the absorbance of the sample, negative control, and positive control at 540 nm, respectively.

[0192] from Figure 5 It can be seen that, regardless of the ratio, the prepared poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethane does not have hemolytic properties.

[0193] In Example 2, the fluorescence images of proteins, platelets, L929 cells, and Escherichia coli adsorbed on the surface of poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethane (PDPAEG-PTHF) (i.e., PDPAEG-PTHF-0, PDPAEG-PTHF-25, PDPAEG-PTHF-50, PDPAEG-PTHF-75, PDPAEG-PTHF-100) are shown below. Figures 6-9 As shown.

[0194] In Example 2, fluorescence images of Staphylococcus epidermidis, Pseudomonas aeruginosa, and Candida albicans adsorbed on the surface of poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethane (PDPAEG-PTHF) (i.e., PDPAEG-PTHF-0, PDPAEG-PTHF-25, PDPAEG-PTHF-50, PDPAEG-PTHF-75, PDPAEG-PTHF-100) are shown, as well as HE-stained images of skin tissue after subcutaneous implantation in rats following polyurethane incubation with Staphylococcus aureus. Figure 10 As shown.

[0195] In Example 2, HE and M&T stained images of skin tissue sections from mice two and four months after implantation of poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran) polyurethane (PDPAEG-PTHF) (i.e., PDPAEG-PTHF-0, PDPAEG-PTHF-25, PDPAEG-PTHF-50, PDPAEG-PTHF-75, PDPAEG-PTHF-100) are shown below. Figure 11 As shown, HE and M&T stained images of skin tissue sections three months after implantation in cynomolgus monkeys are as follows. Figure 12 As shown.

[0196] Figures 6-9 middle, Figure 6 , Figure 7 The Commercial PU is EG-85A. Figure 8 , Figure 9 Commercial PU1 is Lubrizol's Tecophilic TM EG-85A and Commercial PU2 are Lubrizol's Tecophilic products. TM HP-93A.

[0197] Figures 10-12 In the middle, the control sample was Lubrizol's Tecophilic TM EG-85A and Lubrizol's Tecophilic TM HP-93A.

[0198] The preparation method of PEG-PTHF-50 is as follows: Polyethylene glycol (10.34 g, 0.01034 mol) and polytetrahydrofuran (10.34 g, 0.01034 mol) were sequentially added to a three-necked flask purged with nitrogen, followed by the addition of HDI (3.48 g, 0.02068 mol), and the reaction was carried out at 60 °C. Acetone was added in 5 mL increments as the viscosity increased. After 3 days of reaction, anhydrous ethanol was added, and the reaction was continued for 2 hours. The resulting polyurethane was precipitated three times in diethyl ether and dried under vacuum to remove the solvent. The polyurethane was redissolved in acetone, and the resulting polymer solution was poured into a PTFE mold to obtain PEG-PTHF-50.

[0199] Figures 6-9 Fluorescence images showed that PDPAEG-PTHFs exhibited good adsorption properties against proteins, platelets, cells, and E. coli when the DPAEG content exceeded 25%–50% in short-term tests. This was especially true for PDPAEG-PTHF-75 and PDPAEG-PTHF-100. Figure 7 and Figure 10-12Even in long-term testing, it exhibited excellent anti-adsorption properties, demonstrating long-term anti-rejection, anti-thrombotic, and anti-biofilm (including bacterial and fungal) properties. The same conclusions were reached in subcutaneous experiments in mice. Two weeks after subcutaneous implantation, commercial polyurethane, PDPAEG-PTHF-0, and PEG-PTHF-50 materials were densely encapsulated by collagen. The collagen fiber thickness of PDPAEG-PTHF-50 was slightly less than that of PDPAEG-PTHF-25.

[0200] In contrast, PDPAEG-PTHF-75 and PDPAEG-PTHF-100 exhibit extremely thin collagen capsules ( Figure 11 Even four weeks after implantation, fibrosis no longer worsened; on the contrary, the thickness of the PEG-PTHF-50 fibrous capsule continued to increase. The anti-rejection results were further validated in cynomolgus monkeys. Figure 12 ).

[0201] A photograph of PDPAEG-PTHF-100 extruded into a catheter in Example 2 is shown below. Figure 13 As shown, the dried polyurethane (PDPAEG-PTHF-100) can be extruded into conduits. Figure 13 ).

[0202] The free radical scavenging properties of different polyurethane materials, such as PEG-PEHF-50, PDPAEG-PTHF-100, and PCBDA (carboxybetaine hydrogel), are as follows: Figure 14 As shown, from Figure 4 It can be seen that, compared with PEG-PEHF-50, PDPAEG-PTHF-100 can consume DPPH, .OH, and .O2- free radicals, and has excellent antioxidant properties.

[0203] The experimental results of using different polyurethanes, PEG-PEHF-50 and PDPAEG-PTHF-100, as wound repair dressings in mice in Example 2 are as follows: Figure 15 As shown in Example 2, the experimental results of different polyurethanes, PEG-PEHF-50 and PDPAEG-PTHF-100, as wound repair dressings for diabetic rats are as follows: Figure 16 As shown. In full-thickness skin wound models in normal mice and diabetic rats, PDPAEG-PTHF-100 exhibited significant wound-healing function. Figure 15 and 16 ).

[0204] Example 3

[0205] Synthesis of zwitterionic polyurethane (poly(dihydroxypropylglycine methyl ester-glycerol-polytetrahydrofuran))

[0206] The synthetic route of the zwitterionic polyurethane (poly(dihydroxypropylglycine methyl ester-glycerol-polytetrahydrofuran)) precursor is as follows: Figure 17 As shown, the specific method is as follows: DPAEG (15g, 0.073mol), polytetrahydrofuran (4g, 0.004mol), and HDI (13.67g, 0.081mol) were sequentially added to a nitrogen-purged three-necked flask and reacted at 60℃. Acetone was added in 5mL increments as the viscosity increased. After 1 day of reaction, the mixture was cooled and glycerol (0.125g, 0.0014mol) was added. The solution was poured into a polytetrafluoroethylene mold and placed in a 50℃ oven for 12 hours. The temperature was then gradually increased to 100℃, and residual solvent was removed by vacuum. The resulting polyurethane film was immersed in PBS buffer for one week to obtain zwitterionic polyurethane (poly(dihydroxypropylglycine methyl ester-glycerol-polytetrahydrofuran).

[0207] Example 4

[0208] Synthesis of zwitterionic polyurethane (poly(dihydroxypropylglycine ethyl ester-polycaprolactone))

[0209] In this embodiment, the synthetic route of the zwitterionic polyurethane (poly(dihydroxypropylglycine ethyl ester-polycaprolactone)) precursor is as follows: Figure 18 The specific method is as follows: Glycine ethyl ester hydrochloride (0.709 mol, 100 g), potassium bicarbonate (2.128 mol, 214.28 g), and potassium iodide (0.071 mol, 11.835 g) were sequentially added to a three-necked flask containing 1.5 L of acetonitrile, and the temperature was raised to 70 °C. 3-Bromo-1-propanol (1.419 mol, 203.26 g) dissolved in 500 mL of acetonitrile was slowly added dropwise to the mixture, and the reaction was continued for 48 h. Acetonitrile was removed by rotary evaporation, and a large amount of dichloromethane was added. The precipitate was removed by filtration to obtain dihydroxypropylglycine ethyl ester.

[0210] Dihydroxypropyl glycine ethyl ester (9.26 g, 0.045 mol), polycaprolactone (12.89 g, 0.0064 mol), and HDI (8.67 g, 0.052 mol) were sequentially added to a nitrogen-purged three-necked flask and reacted at 80 °C. Acetonitrile was added in 5 mL increments as viscosity increased. After 3 days of reaction, anhydrous ethanol was added to continue the reaction for 6 hours. The resulting polyurethane was precipitated three times in diethyl ether and dried under vacuum to remove the solvent. The molecular weight of the obtained polyurethane was 52427 g / mol (PDI = 1.99). The polyurethane was redissolved in acetonitrile, and the resulting polymer solution was poured into a PTFE mold. After drying, the resulting polyurethane film was immersed in PBS buffer for 4 days to obtain a zwitterionic polyurethane film. In addition, polyurethane was dissolved in dichloromethane (1 mg / mL), and then three different dispersed phases (33.3% Tween 20, 20.0% Tween 80, and 4.0% PVA) were added dropwise at 1500 rpm and stirred for 24 h. The dispersion was centrifuged at 2000 rpm and the solid was washed three times with ultrapure water to obtain polyurethane microspheres, which were then lyophilized to obtain microspheres.

[0211] In this embodiment, a photograph of polyurethane (poly(dihydroxypropylglycine ethyl ester-polycaprolactone)) microspheres is shown below. Figure 19 As shown, a. Micrographs of polymer microspheres prepared in three different dispersed phases. b. Scanning electron micrographs of microspheres prepared in Tween 20. It can be seen that the microsphere structure remains intact.

[0212] Example 5

[0213] Synthesis of zwitterionic polyurethane (poly(dihydroxypropylglycine methyl ester-furan-bismaleimide-polytetrahydrofuran))

[0214] In this embodiment, the synthetic route of the zwitterionic polyurethane (poly(dihydroxypropylglycine methyl ester-furan-bismaleimide-polytetrahydrofuran)) precursor is as follows: Figure 20The specific method is as follows: DPAEG (0.068 mol, 15 g), polytetrahydrofuran (3.8 mmol, 3.8 g), and furanyl dimethyl alcohol (3.8 mmol, 0.49 g) were added to a three-necked flask purged with nitrogen. 20 mL of acetonitrile was added, and the mixture was stirred at 70 °C. Hexamethylene diisocyanate, in an equimolar ratio to the hydroxyl groups, was added, with acetonitrile added as needed to increase viscosity. After reacting for 2 days, 10 mL of anhydrous ethanol was added, and the reaction continued for another 2 hours. The reactants were precipitated in diethyl ether. After drying, the precipitate was redissolved in chloroform. The polymer solution was poured into a polytetrafluoroethylene mold, and 4,4'-bismaleimide diphenylmethane (1.9 mmol, 0.68 g) was added. The mixture was reacted overnight at 50 °C. The temperature was increased to 95 °C until the polyurethane surface in the mold became smooth. The temperature was then returned to 50 °C and maintained for 6 hours to obtain the crosslinked zwitterionic polyurethane precursor. As shown in Table 2, the tensile strength of the polyurethane was increased by 34 times compared to the uncrosslinked polyurethane, i.e., without the addition of 4,4'-bismaleimide diphenylmethane. Soaking the polyurethane in a pH 8 buffer solution for 3 days yielded a zwitterionic polyurethane (poly(dihydroxypropylglycine methyl ester-furan-bismaleimide-polytetrahydrofuran). Even after hydrolysis, its mechanical properties remained superior to those of the uncrosslinked polyurethane.

[0215] In Example 5, the mechanical properties of the polyurethane before and after crosslinking and hydrolysis are shown in Table 2.

[0216] Table 2. Mechanical properties of polyurethane before and after crosslinking and hydrolysis in Example 5

[0217] Tensile strength (MPa) Elongation at break (%) Young's modulus (MPa) Uncrosslinked 0.03 1661 0.1 Crosslinking 1.02 1635 0.1 hydrolysis 0.14 1366 0.01

[0218] Example 6

[0219] Synthesis of zwitterionic polyurethane (poly(dihydroxypropylglycine methyl ester-furan-ureidopyrimidinone-bismaleimide-polytetrahydrofuran))

[0220] In this embodiment, the synthetic route of the zwitterionic polyurethane (poly(dihydroxypropylglycine methyl ester-furan-ureidopyrimidinone-bismaleimide-polytetrahydrofuran)) precursor is as follows: Figure 21As shown, DPAEG (10 g, 0.046 mol), polytetrahydrofuran (2.7 g, 0.0027 mol), and IPDI (12.77 g, 0.057 mol) were sequentially added to a nitrogen-purged three-necked flask and reacted at 70 °C. Tetrahydrofuran was added in 5 mL increments as viscosity increased. Furandimethylol (0.3541 g, 0.0027 mol) dissolved in 5 mL of tetrahydrofuran was added, and the reaction continued for 6 h. UPy (0.46 g, 0.0027 mol) dispersed in anhydrous dimethyl methoxide was added, and the reaction was continued at 70 °C for 4 h. After the reaction was complete, the precipitate was collected in diethyl ether, redissolved in chloroform, and directly used for film deposition. Alternatively, 4,4'-bismaleimide diphenylmethane was added, dried at 100 °C, and then crosslinked at 50 °C. The obtained polyurethane membrane was soaked in PBS buffer for 4 days to obtain zwitterionic polyurethane (poly(dihydroxypropylglycine methyl ester-furan-ureidopyrimidinone-bismaleimide-polytetrahydrofuran)).

[0221] Example 7

[0222] Synthesis of zwitterionic polyurethane (poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran-hydroxyethyl methacrylate))

[0223] In this embodiment, the synthetic route of the zwitterionic polyurethane (poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran-hydroxyethyl methacrylate)) precursor is as follows: Figure 22 As shown, the specific method is as follows: DPAEG (10g, 0.046mol), polytetrahydrofuran (5.07g, 0.00507mol), and IPDI (222.76g, 0.1013mol) were sequentially added to a nitrogen-purged three-necked flask and reacted at 60℃. Acetone was added in 5mL increments as the viscosity increased. After one day of reaction, hydroxyethyl methacrylate (6.87g, 0.051mol) and 0.25% polymerization inhibitor (4-methoxyphenol) were added, and the reaction continued overnight. The reactants were precipitated three times in diethyl ether, redissolved in acetone, and photoinitiator was added. The mixture was then photocured under UV light. The cured polyurethane was then soaked in water for 5 days to obtain zwitterionic poly(dihydroxypropylglycine methyl ester-polytetrahydrofuran-hydroxyethyl methacrylate).

[0224] Example 8

[0225] Synthesis of zwitterionic polyurethane (poly(dihydroxypropyl glycine methyl ester-polycarbonate-polydimethylsiloxane), PDPAEG-PC-PDMS)

[0226] In this embodiment, the synthetic route of the zwitterionic polyurethane (poly(dihydroxypropylglycine methyl ester-polycarbonate-polydimethylsiloxane) precursor is as follows: Figure 23As shown, the specific method is as follows: Polycarbonate (1 eq) and HDI (2 eq) were sequentially added to a three-necked flask purged with nitrogen and reacted at 65°C. After reacting for 1 h, DPAEG (8.9 eq) and IPDI (8 eq) were added, and acetone was added in 5 mL increments as viscosity increased, continuing the reaction for 24 h. After adding PDMS diol (0.1 eq) and reacting for 12 h, anhydrous ethanol was added and the reaction continued for 6 h. The reactants were precipitated three times in diethyl ether, redissolved in acetone, and used for film deposition. The polyurethane film was then soaked in water for 5 days to obtain zwitterionic poly(dihydroxypropylglycine methyl ester-polycarbonate-polydimethylsiloxane (ZPUC)). The tensile strength was 2.29 MPa and the Young's modulus was 5.54 MPa.

[0227] In this embodiment, zwitterionic polyurethane (poly(dihydroxypropylglycine methyl ester-polycarbonate-polydimethylsiloxane)) is used as an abdominal wall hernia repair patch, such as... Figure 24 As shown, commercially available PP mesh adheres tightly to the abdominal wall and intestinal mucosa, while ZPUC membrane exhibits excellent anti-adhesion properties. Figure 24 ).

[0228] The above description of the embodiments is provided to enable those skilled in the art to understand and use the invention. It will be apparent to those skilled in the art that various modifications can be made to these embodiments, and the general principles described herein can be applied to other embodiments without inventive effort. Therefore, the present invention is not limited to the above embodiments, and any improvements and modifications made by those skilled in the art based on the disclosure of the present invention without departing from the scope of the invention should be within the protection scope of the present invention.

Claims

1. An zwitterionic polyurethane or zwitterionic polyurethane precursor, characterized in that, The zwitterionic polyurethane or zwitterionic polyurethane precursor contains one or more zwitterionic groups, or one or more zwitterionic precursor groups, or both zwitterionic groups and zwitterionic precursor groups; The zwitterionic precursor group refers to a group that can be converted into a zwitterionic group by hydrolysis, chemical reaction, heat, radiation, electricity, oxidation, reduction, acid or base treatment; The zwitterionic group is selected from a carboxybetaine, which refers to a molecular structure containing a carboxylate anion and an amine group cation.

2. The zwitterionic polyurethane or zwitterionic polyurethane precursor according to claim 1, characterized in that, The molecular structure of the zwitterionic polyurethane precursor is selected from one of the following: The molecular structure of the zwitterionic polyurethane is selected from one of the following: wherein x, y, z, n are integers selected from 1-1000, R1is selected from one or several of -(CH2)2-, -(CH2)3-, -(CH2) m - -(CH2) r O(CH2) o - -(CH2CH2OCH2CH2) p - -CH2CH2(OCH2CH2) v - R2is selected from one or several of -(CH2)2-, -(CH2)3-, -(CH2) m - -(CH2) r O(CH2) o - -(CH2CH2OCH2CH2) p - -CH2CH2(OCH2CH2) v - R3is selected from one or several of -CH2-, -(CH2)2-, -(CH2) m - -(CH2CH2OCH2CH2) r - -(CH2CH2OCH2CH2) o - -(CH2CH2OCH2CH2) p - -(CH2CH2OCH2CH2) v - -(CH2CH2OCH2CH2) R4 is selected from -O-, -NH- or -S-; R5is selected from -H, -CH3, -(CH2) t CH3, -C(CH3)3, alkyl, alkenyl, alkynyl, carbonyl, targeting ligand, peptide, polyester, polyether, polyamide, monosaccharide, oligosaccharide, polysaccharide, or glycoside; The polyisocyanate containing R6 is selected from one or more of toluene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, hexamethylene diisocyanate trimer, dicyclohexylmethane diisocyanate, naphthalene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, cyclohexyl dimethylene diisocyanate, isosorbide diisocyanate, ethylene glycol diisocyanate, triphenylmethane triisocyanate, propylene glycol diisocyanate or bis(2-isocyanatoethyl) sulfide; The polyol containing R7 is selected from one or more of ethylene glycol, propylene glycol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, neopentyl glycol, 1,2,3-butanetriol, 1,2,6-hexanetriol, glycerol, erythritol, sorbitol, mannitol, xylitol, 2,5-furandimethanol, 2-amino-5-(2-hydroxyethyl)-4(3H)-pyrimidinone, polyether polyol, polyester polyol, polybutylene glycol, polytetramethylene ether glycol, polytetrahydrofurfuryl alcohol, polycaprolactone polyol, polylactic acid polyol, polycarbonate polyol, polyamide polyol, polysiloxane polyol, polyacrylate polyol, polysulfone polyol, polyisobutylene polyol, polystyrene polyol, polyurethane polyol, polyisocyanate polyol, polyester amide polyol or polyepoxy resin polyol; The molecule comprising R8and R9is selected from the group consisting of a polyol comprising R7, a polyol containing a zwitterionic or zwitterionic precursor group, a zwitterionic or zwitterionic precursor group, an alcohol, an amine, a carboxylic acid, CH3(CH2) w OH, methanol, ethanol, propanol, isopropanol, isobutanol, butanol, hexanol, pentanol, an alkyl alcohol, an aromatic alcohol, CH3(CH2) u NH2, methylamine, ethylamine, propylamine, isopropylamine, isobutylamine, butylamine, hexylamine, pentylamine, an alkyl amine, an aromatic amine, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 6-hydroxyhexyl acrylate, glyceryl acrylate, glyceryl methacrylate, 4-hydroxyphenyl acrylate, 4-hydroxyphenyl methacrylate, 3-(N,N-dimethylamino)propyl acrylate, 3-(N,N-dimethylamino)propyl methacrylate, hydroxyl-terminated polyethylene glycol acrylate, hydroxyl-terminated polyethylene glycol methacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, hydroxyl-terminated polypropylene glycol acrylate, hydroxyl-terminated polypropylene glycol methacrylate, hydroxyl-terminated polytetramethylene ether glycol diacrylate, hydroxyl-terminated polytetramethylene ether glycol dimethacrylate, hydroxyl-containing polyurethane acrylate, hydroxyl-containing polyester acrylate, hydroxyl-terminated polyester methacrylate, hydroxyl-containing polyether acrylate, hydroxyl-terminated polyether methacrylate, 2-hydroxy-3-propyl acrylate, 2-hydroxy-3-butyl acrylate, 2-hydroxy-3-methylbutyl acrylate, 2-hydroxyethyl-2-methylpropyl acrylate, 2-hydroxyethyl-3-methylbutyl acrylate, 2-hydroxyethyl-4-methylpentyl acrylate, 3-hydroxy-3-methylbutyl methacrylate, tetraphenyl ethylene alcohol, 9,10-dihydroxyanthracene, 2-hydroxy-1,8-naphthalimide, 9-hydroxyfluorenone, a coumarin hydroxyl derivative, a hydroxyl-containing fluorescein, a hydroxyl-containing porphyrin derivative, a hydroxyl-containing benzothiazole and benzimidazole derivative, a hydroxyl-containing stilbene derivative, a hydroxyl-containing polystyrene derivative, one or several of wherein m, r, o, p, v, t, w, u are independently selected from integers from 1 to 1000; wherein the polymer has a molecular weight of 1000 to 1000000 g / mol.

3. The zwitterionic polyurethane or zwitterionic polyurethane precursor of claim 2, wherein, The molecular structure of the zwitterionic group or zwitterionic precursor group is selected from one or more of the following: R1 is independently selected from -(CH2)2-, -(CH2)3-, and -(CH2). r -、-(CH2) n O(CH2) s -、-(CH2CH2OCH2CH2) t -, -CH2CH2(OCH2CH2) u - one or more of them; R2 is independently selected from -(CH2)2-, -(CH2)3-, and -(CH2). r -、-(CH2) n O(CH2) s -、-(CH2CH2OCH2CH2) t -, -CH2CH2(OCH2CH2) u - one or more of them; R3is independently selected from one or more of -CH2-, -(CH2)2-, -(CH2) r - -(CH2) n O(CH2) s - -(CH2CH2OCH2CH2) t - -CH2CH2(OCH2CH2) u - R4 is independently selected from -O-, -NH- or -S-, R5is independently selected from -H, -CH3, -(CH2) v CH3, -C(CH3)3, alkyl, alkenyl, alkynyl, polyester, polyether, polyamide, monosaccharide, oligosaccharide, polysaccharide, or glycoside; R7is independently selected from H-, CH3-, CH3CH2-, CH3(CH2) y -, CH3O-(CH2CH2O) z CH2CH2-, ethyl bromoacetate, methyl bromoacetate, alkyl bromoacetate, tert-butyl bromopropionate, methyl bromopropionate, tert-butyl bromopropionate, alkyl bromopropionate, tert-butyl bromobutyrate, methyl bromobutyrate, tert-butyl bromobutyrate, alkyl bromobutyrate; A - independently selected from F - , Cl - , Br - , I - , SO4 2- , NO3 - , CO3 2- , PO4 3- , SiO3 2- , ClO4 - , CrO4 2- , PF6 - , BF4 - , CF3SO3 - , SiF6 2- , CN - , SCN - , OCN - , HCOO - , CH3COO - , C2O4 2- , C6H5O7 3- , C6H5COO - , CF3COO - , CF3SO3 - , N(CF3SO2)2 2- one or several organic or inorganic anions; M + independently selected from Li + , Na + , K + , Ca 2+ , Mg 2+ , Fe 2+ , Fe 3+ , Zn 2+ and the like inorganic metal cations, or one or more of quaternary ammonium cations, phosphonium cations and the like organic cations; wherein n, r, s, t, u, v, y, z are independently selected from integers from 1 to 1000; wherein the polymer has a molecular weight of about 1000 to about 1000000 g / mol.

4. The zwitterionic polymer or zwitterionic polyurethane precursor of claim 1 or 2, wherein, The molecular structure of the zwitterionic polymer is selected from one of the following: wherein x, y, n are integers selected from 1-1000, R1is selected from one or more of -(CH2)2-, -(CH2)3-, -(CH2) m - -(CH2) r O(CH2) o - -(CH2CH2OCH2CH2) p - -CH2CH2(OCH2CH2) v - R2is selected from one or several of -(CH2)2-, -(CH2)3-, -(CH2) m - -(CH2) r O(CH2) o - -(CH2CH2OCH2CH2) p - -CH2CH2(OCH2CH2) v - R3is selected from one or several of -CH2-, -(CH2)2-, -(CH2) m - -(CH2) r O(CH2) o - -(CH2CH2OCH2CH2) p - -CH2CH2(OCH2CH2) v - The polyisocyanate comprising R4 is selected from one or more of toluene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, hexamethylene diisocyanate trimer, dicyclohexylmethane diisocyanate, naphthalene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, cyclohexyl dimethylene diisocyanate, isosorbide diisocyanate, ethylene glycol diisocyanate, triphenylmethane triisocyanate, propylene glycol diisocyanate, and bis(2-isocyanatoethyl) sulfide; The polyol comprising R5 is selected from one or more of ethylene glycol, propylene glycol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, neopentyl glycol, 1,2,3-butanetriol, 1,2,6-hexanetriol, glycerol, erythritol, sorbitol, mannitol, xylitol, 2,5-furandimethanol, 2-amino-5-(2-hydroxyethyl)-4(3H)-pyrimidinone, polyether polyols, polyester polyols, polybutylene glycol, polytetramethylene ether glycol, polytetrahydrofurfuryl alcohol, polycaprolactone polyols, polylactic acid polyols, polycarbonate polyols, polyamide polyols, polysiloxane polyols, polyacrylate polyols, polysulfone polyols, polyisobutylene polyols, polystyrene polyols, polyurethane polyols, polyisocyanate polyols, polyester amide polyols, polyepoxy resin polyols; The molecule comprising R6and R7is selected from the group consisting of a polyol comprising R5, a polyol containing a zwitterionic or zwitterionic precursor group, a zwitterionic or zwitterionic precursor group, an alcohol, an amine, a carboxylic acid, CH3(CH2) w OH, methanol, ethanol, propanol, isopropanol, isobutanol, butanol, hexanol, pentanol, an alkyl alcohol, an aromatic alcohol, CH3(CH2) u NH2, methylamine, ethylamine, propylamine, isopropylamine, isobutylamine, butylamine, hexylamine, pentylamine, an alkyl amine, an aromatic amine, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 6-hydroxyhexyl acrylate, glyceryl acrylate, glyceryl methacrylate, 4-hydroxyphenyl acrylate, 4-hydroxyphenyl methacrylate, 3-(N,N-dimethylamino)propyl acrylate, 3-(N,N-dimethylamino)propyl methacrylate, hydroxyl-terminated polyethylene glycol acrylate, hydroxyl-terminated polyethylene glycol methacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, hydroxyl-terminated polypropylene glycol acrylate, hydroxyl-terminated polypropylene glycol methacrylate, hydroxyl-terminated polytetramethylene ether glycol diacrylate, hydroxyl-terminated polytetramethylene ether glycol dimethacrylate, hydroxyl-containing polyurethane acrylate, hydroxyl-containing polyester acrylate, hydroxyl-terminated polyester methacrylate, hydroxyl-containing polyether acrylate, hydroxyl-terminated polyether methacrylate, 2-hydroxy-3-propyl acrylate, 2-hydroxy-3-butyl acrylate, 2-hydroxy-3-methylbutyl acrylate, 2-hydroxyethyl-2-methylpropyl acrylate, 2-hydroxyethyl-3-methylbutyl acrylate, 2-hydroxyethyl-4-methylpentyl acrylate, 3-hydroxy-3-methylbutyl methacrylate, tetraphenyl ethylene alcohol, 9,10-dihydroxyanthracene, 2-hydroxy-1,8-naphthalimide, 9-hydroxyfluorenone, a coumarin hydroxyl derivative, a hydroxyl-containing fluorescein, a hydroxyl-containing porphyrin derivative, a hydroxyl-containing benzothiazole and benzimidazole derivative, a hydroxyl-containing stilbene derivative, a hydroxyl-containing polystyrene derivative, one or several of wherein m, r, o, p, v, t, w, u are independently selected from an integer from 1 to 1000; wherein the polymer has a molecular weight of 1000 to 1000000 g / mol.

5. The zwitterionic polyurethane or zwitterionic polyurethane precursor of claim 2, wherein, The molecular structure of the zwitterionic polyurethane is selected from one of the following: wherein x, y, n are selected from an integer from 1 to 1000, R1 is selected from -(CH2)2- or -(CH2)3-; R2 is selected from -(CH2)2-, -(CH2)3-; R3 is selected from -CH2-, -(CH2)2-; R4 is selected from one or more of hexamethylene diisocyanate, hexamethylene diisocyanate trimer, isophorone diisocyanate, dicyclohexylmethane diisocyanate; R5 is selected from one or more of ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, polybutylene glycol, polycarbonate polyols, polytetramethylene ether glycol, polyester polyols; R6 is selected from -H, -CH3, -CH2CH3, -C(CH3)3; R7 is selected from hydroxyethyl acrylate, hydroxyethyl methacrylate.

6. The zwitterionic polyurethane or zwitterionic polyurethane precursor of claim 2, wherein, The molecular structure of the zwitterionic polyurethane is selected from one of the following: wherein m, n, o, x, y, z are independently selected from an integer from 1 to 1000.

7. A method of preparing a zwitterionic polyurethane or zwitterionic polyurethane precursor according to claim 2, wherein, The method of preparing the zwitterionic polyurethane comprises the following steps: obtaining an intermediate polymer by polymerization of a zwitterionic precursor diol, a polyisocyanate, and a polyol, and then removing the side chains of the intermediate polymer to obtain the zwitterionic polyurethane, wherein The zwitterionic precursor diol is selected from the following structure: The polyisocyanate is selected from the following structure: said polyol is selected from one of the following structures: R7-(OH) p ; The intermediate polymer is selected from one of the following structures: wherein x, y, n are selected from an integer from 1 to 1000, R1is selected from one or several of -(CH2)2-, -(CH2)3-, -(CH2) m - -(CH2) r O(CH2) o - -(CH2CH2OCH2CH2) p - -CH2CH2(OCH2CH2) v - R2is selected from one or several of -(CH2)2-, -(CH2)3-, -(CH2) m - -(CH2) r O(CH2) o - -(CH2CH2OCH2CH2) p - -CH2CH2(OCH2CH2) v - R3is selected from one or several of -CH2-, -(CH2)2-, -(CH2) m - -(CH2CH2OCH2CH2) r - -(CH2CH2OCH2CH2) o - -(CH2CH2OCH2CH2) p - -(CH2CH2OCH2CH2) v - -(CH2CH2OCH2CH2) R4is selected from -O-, -NH- or -S-, R5is selected from -H, -CH3, -(CH2) t CH3, -C(CH3)3, alkyl, alkenyl, alkynyl, carbonyl, targeting ligand, peptide, polyester, polyether, polyamide, monosaccharide, oligosaccharide, polysaccharide, or glycoside; the polyfunctional isocyanate comprising R6is selected from one or more of toluene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, hexamethylene diisocyanate trimer, dicyclohexylmethane diisocyanate, naphthalene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, cyclohexyl dimethylene diisocyanate, isosorbide diisocyanate, ethylene glycol diisocyanate, triphenylmethane triisocyanate, propylene glycol diisocyanate, and bis(2-isocyanatoethyl) sulfide; the polyol comprising R7is selected from one or more of ethylene glycol, propylene glycol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, neopentyl glycol, 1,2,3-butanetriol, 1,2,6-hexanetriol, glycerol, erythritol, sorbitol, mannitol, xylitol, 2,5-furandimethanol, 2-amino-5-(2-hydroxyethyl)-4(3H)-pyrimidinone, polyether polyols, polyester polyols, polybutylene glycol, polytetramethylene ether glycol, polytetrahydrofurfuryl alcohol, polycaprolactone polyols, polylactic acid polyols, polycarbonate polyols, polyamide polyols, polysiloxane polyols, polyacrylate polyols, polysulfone polyols, polyisobutylene polyols, polystyrene polyols, polyurethane polyols, polyisocyanate polyols, polyesteramide polyols, polyepoxy resin polyols; The molecule comprising R8and R9is selected from the group consisting of a polyol comprising R7, a polyol containing a zwitterionic or zwitterionic precursor group, a zwitterionic or zwitterionic precursor group, an alcohol, an alcohol, an amine, a carboxylic acid, CH3(CH2) w OH, methanol, ethanol, propanol, isopropanol, isobutanol, butanol, hexanol, pentanol, an alkyl alcohol, an aromatic alcohol, CH3(CH2) u NH2, methylamine, ethylamine, propylamine, isopropylamine, isobutylamine, butylamine, hexylamine, pentylamine, an alkyl amine, an aromatic amine, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 6-hydroxyhexyl acrylate, glyceryl acrylate, glyceryl methacrylate, 4-hydroxyphenyl acrylate, 4-hydroxyphenyl methacrylate, 3-(N,N-dimethylamino)propyl acrylate, 3-(N,N-dimethylamino)propyl methacrylate, hydroxyl-terminated polyethylene glycol acrylate, hydroxyl-terminated polyethylene glycol methacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, hydroxyl-terminated polypropylene glycol acrylate, hydroxyl-terminated polypropylene glycol methacrylate, hydroxyl-terminated polytetramethylene ether glycol diacrylate, hydroxyl-terminated polytetramethylene ether glycol dimethacrylate, hydroxyl-containing polyurethane acrylate, hydroxyl-containing polyester acrylate, hydroxyl-terminated polyester methacrylate, hydroxyl-containing polyether acrylate, hydroxyl-terminated polyether methacrylate, 2-hydroxy-3-propyl acrylate, 2-hydroxy-3-butyl acrylate, 2-hydroxy-3-methylbutyl acrylate, 2-hydroxyethyl-2-methylpropyl acrylate, 2-hydroxyethyl-3-methylbutyl acrylate, 2-hydroxyethyl-4-methylpentyl acrylate, 3-hydroxy-3-methylbutyl methacrylate, tetraphenyl ethylene alcohol, 9,10-dihydroxyanthracene, 2-hydroxy-1,8-naphthalimide, 9-hydroxyfluorenone, a coumarin hydroxyl derivative, a hydroxyl-containing fluorescein, a hydroxyl-containing porphyrin derivative, a hydroxyl-containing benzothiazole and benzimidazole derivative, a hydroxyl-containing stilbene derivative, a hydroxyl-containing polystyrene derivative, one or several of wherein m, r, o, p, v, t, w, u are independently selected from an integer from 1 to 1000; wherein the polymer has a molecular weight of 1000 to 1000000 g / mol.

8. A method of preparing a zwitterionic polyurethane or zwitterionic polyurethane precursor according to claim 2, wherein, The method of preparing the zwitterionic polyurethane comprises the following steps: obtaining an intermediate polymer by polymerization of a zwitterionic precursor diol, a polyfunctional isocyanate, and then removing the side chains of the intermediate polymer to obtain the zwitterionic polyurethane, wherein the zwitterionic precursor diol is selected from the following structure: the polyfunctional isocyanate is selected from the following structure: the intermediate polymer is selected from one of the following structures: wherein the selection of R1-R8, m, n, r, o, p, v, t, w, u is the same as the zwitterionic polyurethane.

9. A method of preparing a zwitterionic polyurethane or zwitterionic polyurethane precursor according to claim 2, wherein, The method of preparing the zwitterionic polyurethane comprises the following steps: obtaining the zwitterionic polyurethane by polymerization of a zwitterionic diol or a zwitterionic precursor diol, a polyol, and a polyfunctional isocyanate, wherein the zwitterionic diol is selected from the following structure: The zwitterionic precursor diol is selected from the following structures: R7-(OH) p the polyfunctional isocyanate is selected from the following structure: the zwitterionic polyurethane is selected from one of the following structures: wherein x, y, n are selected from an integer from 1 to 1000; R1is selected from one or more of -(CH2)2-, -(CH2)3-, -(CH2) r - -(CH2) m O(CH2) s - -(CH2CH2OCH2CH2) t - -CH2CH2(OCH2CH2) u - R2is selected from one or several of -(CH2)2-, -(CH2)3-, -(CH2) r - -(CH2) m O(CH2) s - -(CH2CH2OCH2CH2) t - -CH2CH2(OCH2CH2) u - R3is selected from one or more of -CH2-, -(CH2)2-, -(CH2)3-, r -(CH2)4-, m -(CH2)5-, s -(CH2)6-, t -(CH2)7-, u -(CH2)8-, and -CH2CH2(OCH2CH2) R4is selected from -O-, -NH- or -S-, R5is selected from -H, -CH3, -(CH2) v CH3, -C(CH3)3, alkyl, alkenyl, alkynyl, polyester, polyether, polyamide, monosaccharide, oligosaccharide, polysaccharide, or glycoside; The polyisocyanate comprising R6 is selected from one or more of toluene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, dicyclohexylmethane diisocyanate, naphthalene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, cyclohexyl dimethylene diisocyanate, isosorbide diisocyanate, ethylene glycol diisocyanate, triphenylmethane triisocyanate, propylene glycol diisocyanate, and bis(2-isocyanatoethyl) sulfide; The polyol comprising R7 is selected from one or more of ethylene glycol, propylene glycol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, neopentyl glycol, 1,2,3-butanetriol, 1,2,6-hexanetriol, glycerol, erythritol, sorbitol, mannitol, xylitol, a polyether polyol, a polyester polyol, a polybutylene glycol, a polytetramethylene ether glycol, a polytetrahydrofurfuryl alcohol, a polycaprolactone polyol, a polylactic acid polyol, a polycarbonate polyol, a polyamide polyol, a polysiloxane polyol, a polyacrylate polyol, a polysulfone polyol, a polyisobutylene polyol, a polystyrene polyol, a polyurethane polyol, a polyisocyanate polyol, a polyester amide polyol, and a polyepoxy resin polyol; The molecule comprising R8and R9is selected from the group consisting of a polyol comprising R7, a zwitterionic or zwitterionic precursor group-containing polyol, an amine, a carboxylic acid, CH3(CH2) w OH, methanol, ethanol, propanol, isopropanol, isobutanol, butanol, hexanol, pentanol, an alkyl alcohol, an aromatic alcohol, CH3(CH2) o NH2, methylamine, ethylamine, propylamine, isopropylamine, isobutylamine, butylamine, hexylamine, pentylamine, an alkyl amine, an aromatic amine, dihydroxypolyethylene glycol, dihydroxypolytetrahydrofuran, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 6-hydroxyhexyl acrylate, glyceryl acrylate, glyceryl methacrylate, 4-hydroxyphenyl acrylate, 4-hydroxyphenyl methacrylate, 3-(N,N-dimethylamino)propyl acrylate, 3-(N,N-dimethylamino)propyl methacrylate, hydroxyl-terminated polyethylene glycol acrylate, hydroxyl-terminated polyethylene glycol methacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, hydroxyl-terminated polypropylene glycol acrylate, hydroxyl-terminated polypropylene glycol methacrylate, hydroxyl-terminated polytetramethylene ether glycol diacrylate, hydroxyl-terminated polytetramethylene ether glycol dimethacrylate, hydroxyl-containing polyurethane acrylate, hydroxyl-containing polyester acrylate, hydroxyl-terminated polyester methacrylate, hydroxyl-containing polyether acrylate, hydroxyl-terminated polyether methacrylate, 2-hydroxy-3-propyl acrylate, 2-hydroxy-3-butyl acrylate, 2-hydroxy-3-methylbutyl acrylate, 2-hydroxyethyl-2-methylpropyl acrylate, 2-hydroxyethyl-3-methylbutyl acrylate, 2-hydroxyethyl-4-methylpentyl acrylate, 3-hydroxy-3-methylbutyl methacrylate, tetraphenyl ethylene alcohol, 9,10-dihydroxyanthracene, 2-hydroxy-1,8-naphthalimide, 9-hydroxyfluorenone, coumarin hydroxyl derivatives, hydroxyl-containing fluorescein, hydroxyl-containing porphyrin derivatives, hydroxyl-containing benzothiazole and benzimidazole derivatives, hydroxyl-containing stilbene derivatives, hydroxyl-containing polystyrene derivatives, one or more of R 10 H-, CH3-, CH3CH2-, CH3(CH2) p -, CH3O-(CH2CH2O) q CH2CH2-, ethyl bromoacetate, methyl bromoacetate, alkyl bromoacetate, tert-butyl bromopropionate, methyl bromopropionate, tert-butyl bromopropionate, alkyl bromopropionate, tert-butyl bromobutyrate, methyl bromobutyrate, tert-butyl bromobutyrate, alkyl bromobutyrate; A - selected from F - , CI - , Br - , I - , SO4 2- , NO3 - , CO3 2- , PO4 3- , SiO3 2- , ClO4 - , CrO4 2- , PF6 - , BF4 - , CF3SO3 - , SiF6 2- , CN - , SCN - , OCN - , HCOO - , CH3COO - , C2O4 2- , C6H5O7 3- , C6H5COO - , CF3COO - , CF3SO3 - , N(CF3SO2)2 2- , one or several organic or inorganic anions; M + independently selected from Li + , Na + , K + , Ca 2+ , Mg 2+ , Fe 2+ , Fe 3+ , Zn 2+ and the like inorganic metal cations, or one or more of quaternary ammonium cations, phosphonium cations and the like organic cations; wherein m, o, p, q, r, s, t, u, v, w are independently selected from an integer from 1 to 1000; wherein the polymer has a molecular weight of about 1000 to about 1,000,000 g / mol.

10. The zwitterionic polyurethane or zwitterionic polyurethane precursor of any one of claims 1-6, or the zwitterionic polyurethane or zwitterionic polyurethane precursor prepared by the method of any one of claims 7-9, for use in the preparation of a medical device, a drug carrier, or a biomaterial.

11. Use according to claim 10, characterized in that, The medical device comprises an interventional device or implant, an extracorporeal circulation device, or an in vitro diagnostic device.

12. Use according to claim 11, characterized in that, The interventional device or implant is a medical catheter, a vascular prosthesis, a stent, a valve, a patch, a dressing, or a biosensor.

13. The use according to claim 10, characterized in that, The use comprises blending the zwitterionic polyurethane or zwitterionic polyurethane precursor as a toughener or anti-fouling modifier with a polymeric material for the preparation of the medical device, the drug carrier, or the biomaterial.

14. The use according to claim 10, characterized in that, The drug carrier is a nanoparticle, a fiber, or a hydrogel based on the zwitterionic polyurethane or zwitterionic polyurethane precursor.

15. The use according to claim 10, characterized in that, The biomaterial comprises a tissue engineering scaffold or a medical aesthetic filler.

16. A dressing or tissue repair scaffold for promoting wound healing, which is made of the zwitterionic polyurethane of any one of claims 1-6, or the polyurethane prepared by the method of any one of claims 7-9; the wound comprises a chronic wound, a traumatic wound, or a burn wound.

17. The dressing or tissue repair scaffold of claim 16, wherein, The chronic wound is a diabetic foot ulcer or a pressure sore.

18. A wound care product comprising the zwitterionic polyurethane of any one of claims 1-6, or the polyurethane prepared by the method of any one of claims 7-9; the product is a wound dressing, an artificial skin, a scar inhibiting gel, or a tissue adhesive.

19. An anti-biofouling article comprising the zwitterionic polyurethane of any one of claims 1-6, or the polyurethane prepared by the method of any one of claims 7-9; the article is a medical device, a water treatment membrane, a food industry equipment, a household hygiene product, a marine equipment protective structure, an industrial pipe, a heat exchanger, or a functional textile.

20. The article of claim 19, wherein, The biofouling comprises at least one of organic molecule adsorption, biological molecule adsorption, protein adsorption, bacterial adhesion, fungal adhesion, viral adhesion, biofilm formation, thrombosis, foreign body reaction, biological calcification, algal attachment, or marine organism attachment.

21. Use of the zwitterionic polyurethane of any one of claims 1-6, or the polyurethane prepared by the method of any one of claims 7-9, in inhibiting non-specific adsorption of biological molecules or organisms.

22. A composition comprising the zwitterionic polyurethane of any one of claims 1-6, or the polyurethane prepared by the method of any one of claims 7-9, and a pharmaceutically acceptable carrier, an industrial polymeric matrix, or a coating solvent.

23. A method of making an anti-biofouling article comprising: The zwitterionic polyurethane of any one of claims 1-6, or the polyurethane prepared by the method of any one of claims 7-9, is applied to a substrate or an article surface by means of application, blending, impregnation, or molding processing.

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