IODINE COMPLEX AND PREPARATION METHOD THEREFOR AND USE THEREOF

Abstract

An iodine complex is formed by complexing a unit having a structure as represented by formula (I) with iodine molecules or iodine molecules with polyiodide ions formed by combining iodine ions. As a carrier, a polymer is complexed with iodine to obtain an iodine complex for formula (I).

##STR00001##

The iodine complex can be used as a radioactive marker, or used in an iodine therapeutic agent, or used in a polarizer. The polymer carrier has good biocompatibility. The content of iodine in the iodine complex can be adjusted according to requirements, and the content of the iodine can be adjusted within a range of 0.001-60%. The difference in the content of the iodine can affect the transmission clarity of the iodine complex as a radiographic marker.

Claims

1. An iodine complex, wherein the iodine complex is obtained by complexing a polymer containing a structural unit represented by Formula (I) and optionally at least one of the structural units represented by Formula (II), Formula (III) and Formula (IV) as a carrier with iodine: ##STR00011## in Formula (I), R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are the same or different, independently selected from H, C.sub.1-8 alkyl, C.sub.6-20 aryl that is unsubstituted or optionally substituted by one, two or more R.sub.a; each R.sub.a is the same or different, independently selected from C.sub.1-12 alkyl; a, b, c, d, e and f are independently integers greater than or equal to 0, and a and e are not 0 at the same time; in Formula (II), R.sub.19 is selected from H, cyano, C.sub.1-8 alkyl, the following groups that are unsubstituted or optionally substituted by one, two or more R.sub.a: C.sub.3-10 cycloalkyl, C.sub.6-20 aryl; each R.sub.a is the same or different, independently selected from C.sub.1-12 alkyl; g is an integer greater than or equal to 1; in Formula (III), R.sub.13, R.sub.16, R.sub.17 and R.sub.18 are the same or different, independently selected from H, C.sub.1-8 alkyl, C.sub.6-20 aryl that is unsubstituted or optionally substituted by one, two or more R.sub.a; each R.sub.a is the same or different, independently selected from C.sub.1-12 alkyl; h, i, j, k and n′ are independently integers greater than or equal to 1; in Formula (IV), R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12 are the same or different, independently selected from H, C.sub.1-8 alkyl, C.sub.6-20 aryl that is unsubstituted or optionally substituted by one, two or more R.sub.a; each R.sub.a is the same or different, independently selected from C.sub.1-12 alkyl; a′, b′, c′, d′, e′ and f′ are independently integers greater than or equal to 0, and are not 0 at the same time.

2. Use of a polymer comprising a structural unit represented by Formula (I) and optionally at least one of structural units represented by Formula (II), Formula (III) and Formula (IV) as iodine carrier, wherein the use comprises: a polymer comprising a structural unit represented by Formula (I) and optionally at least one of structural units represented by Formula (II), Formula (III) and Formula (IV) as a carrier is complexed with iodine to obtain an iodine complex: ##STR00012## in Formula (I), R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are the same or different, independently selected from H, C.sub.1-8 alkyl, C.sub.6-20 aryl that is unsubstituted or optionally substituted by one, two or more R.sub.a; each R.sub.a is the same or different, independently selected from C.sub.1-12 alkyl; a, b, c, d, e and f are independently integers greater than or equal to 0, and a and e are not 0 at the same time; in Formula (II), R.sub.19 is selected from H, cyano, C.sub.1-8 alkyl, the following groups that are unsubstituted or optionally substituted by one, two or more R.sub.a: C.sub.3-10 cycloalkyl, C.sub.6-20 aryl; each R.sub.a is the same or different, independently selected from C.sub.1-12 alkyl; g is an integer greater than or equal to 1; in Formula (III), R.sub.13, R.sub.16, R.sub.17 and R.sub.18 are the same or different, independently selected from H, C.sub.1-8 alkyl, C.sub.6-20 aryl that is unsubstituted or optionally substituted by one, two or more R.sub.a; each R.sub.a is the same or different, independently selected from C.sub.1-12 alkyl; h, i, j, k and n′ are independently integers greater than or equal to 1; in Formula (IV), R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12 are the same or different, independently selected from H, C.sub.1-8 alkyl, C.sub.6-20 aryl that is unsubstituted or optionally substituted by one, two or more R.sub.a; each R.sub.a is the same or different, independently selected from C.sub.1-12 alkyl; a′, b′, c′, d′, e′ and f′ are independently integers greater than or equal to 0, and are not 0 at the same time.

3. The iodine complex according to claim 1, wherein, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are the same or different, independently selected from H, C.sub.1-4 alkyl, C.sub.6-10 aryl that is unsubstituted or optionally substituted by one, two or more R.sub.a; R.sub.a is as defined above. Preferably, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are the same or different, independently selected from H, methyl, phenyl, tolyl; further preferably, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are the same or different, independently selected from H, methyl; further preferably, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are the same, selected from H. Preferably, a is an integer between 0-20,000; preferably, a is an integer between 50-3,000. Preferably, b is an integer between 0-2,000, c is an integer between 0-2,000, d is an integer between 0-2,000, e is an integer between 0-20,000, f is an integer between 0-2,000.

4. The iodine complex according to claim 1, wherein, R.sub.19 is selected from H, cyano, C.sub.1-4 alkyl, C.sub.6-10 aryl that is unsubstituted or optionally substituted by one, two or more R.sub.a; R.sub.a is as defined above; preferably, R.sub.19 is selected from phenyl, tolyl, cyano. Preferably, g is an integer between 0-10,000.

5. The iodine complex according to claim 4, wherein, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12 are the same or different, independently selected from H, C.sub.1-4 alkyl, C.sub.6-10 aryl that is unsubstituted or optionally substituted by one, two or more R.sub.a; R.sub.a is as defined above; preferably, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12 are the same or different, independently selected from H, methyl, phenyl, tolyl; preferably, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12 are the same or different, independently selected from H, methyl; further preferably, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12 are the same, selected from H. Preferably, a′ is an integer between 0-20,000, b′ is an integer between 0-2,000, c′ is an integer between 0-2,000, d′ is an integer between 0-2,000, e′ is an integer between 0-10,000, f′ is an integer between 0-2,000. Preferably, a′ and e′ are not 0 at the same time. Preferably, R.sub.13, R.sub.16, R.sub.17 and R.sub.18 are the same or different, independently selected from H, C.sub.1-4 alkyl, C.sub.6-10 aryl that is unsubstituted or optionally substituted by one, two or more R.sub.a; R.sub.a is as defined above; preferably, R.sub.13, R.sub.16, R.sub.17 and R.sub.18 are the same or different, independently selected from H, methyl, phenyl, tolyl; preferably, R.sub.13, R.sub.16, R.sub.17 and R.sub.18 are the same or different, independently selected from H, methyl; further preferably, R.sub.13, R.sub.16, R.sub.17 and R.sub.18 are the same, selected from H. Preferably, h is an integer between 0-2,000, i is an integer between 0-2,000, j is an integer between 0-2,000, k is an integer between 0 and 2,000. Preferably, n′ is an integer between 1-10; preferably, n′ is 1 or 2.

6. The iodine complex according to claim 1, wherein, the iodine is one of an iodine molecule, and a polyiodide formed by binding an iodine molecule with iodide ion, or a mixture of them. Preferably, the polymer is a homopolymer, a random copolymer or a block copolymer. Preferably, a weight ratio of the polymer and iodine in the iodine complex is 1:0.00001-1.5.

7. A preparation method of the iodine complex according to claim 1, wherein, the method comprises the following steps: reacting a polymer comprising a structural unit represented by Formula (I) and optionally at least one of structural units represented by Formula (II), Formula (III) and Formula (IV) with iodine to prepare the iodine complex; wherein, the reaction may be a gas-solid reaction, a solid-liquid reaction or a liquid-liquid homogeneous reaction; the gas-solid reaction is a reaction by contacting an iodine-containing gas with a polymer solid comprising the structural unit represented by Formula (I) and optionally at least one of structural units represented by Formula (II), Formula (III) and Formula (IV); the solid-liquid reaction is a reaction between an iodine-containing solution and a polymer solid comprising the structural unit represented by Formula (I) and optionally at least one of structural units represented by Formula (II), Formula (III) and Formula (IV); the liquid-liquid homogeneous reaction is a homogeneous reaction after mixing an iodine-containing solution and a solution of the polymer comprising the structural unit represented by Formula (I) and optionally at least one of structural units represented by Formula (II), Formula (III) and Formula (IV).

8. The preparation method according to claim 7, wherein, the temperature of the reaction is, for example, from minus 20° C. to 110° C., the reaction time is from 0.5 h to 250 h. Preferably, the polymer containing the structural unit represented by Formula (I) can be prepared by the following method: (i) an epoxidized polymer is prepared by oxidation reaction of a polymer containing the structural unit represented by Formula (V), ##STR00013## in Formula (V), x=a+b+c, y=d+e+f; R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, a, b, c, d, e and f are as defined above; (ii) the polymer products are obtained by hydrolysis of the epoxidized polymer, or by hydrolysis first and then catalytic hydrogenation; or by catalytic hydrogenation first and then hydrolysis.

9. The preparation method according to claim 7, wherein, the polymer comprising the structural unit represented by Formula (V) may further comprise at least one of the structural units that represented by Formula (II), Formula (VI) and Formula (VII): ##STR00014## in Formula (II), R.sub.19 and g are as defined above; ##STR00015## in Formula (VI), n=h+i+j+k, R.sub.13, R.sub.16, R.sub.17, R.sub.18, h, i, j, k and n′ are as defined above; ##STR00016## in Formula (VII), x′=a′+b′+c′, y′=d′±e′+f′; R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, a′, b′, c′, d′, e′ and fare as defined above.

10. Use of the iodine complex according to claim 1 a radiation marker, or in an iodine therapeutic agent, or in a polarizing film. Preferably, the radiation marker is a radiopaque marker.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0079] FIG. 1 is an industrial CT scan image of the iodine complex film of Example 5.

[0080] FIG. 2 is a TGA diagram of the iodine complex of Example 5.

DETAILED DESCRIPTION OF THE INVENTION

[0081] The present invention will be further illustrated with reference to the specific examples below. It should be understood that these examples below are only used to exemplify the present invention, but are not intended to limit the scope of the present invention. Any technique achieved basing on the above contents of the invention also fall within the scope intended to be protected by the present invention.

[0082] Unless otherwise specified, the experimental methods used in the following examples are conventional methods; unless otherwise specified, the reagents and materials used in the following examples can be obtained from commercial sources.

[0083] Instruments and Equipments

[0084] Material structure test .sup.1H NMR and .sup.13CNMR is carried out on JOEL's 600M pulse Fourier transform nuclear magnetic resonance spectrometer;

[0085] IR is tested on Thermofisher's Fourier Transform Infrared Spectrometer Nicolet IS50;

[0086] Tg value is tested on Q100 Differential Scanning calorimeter, TA Company;

[0087] TGA is tested on Q500 thermogravimetric analyzer, TA company;

[0088] The molecular weight of the polymer is tested on Agilent's PL-GPC50 (with a refractive index detector and an evaporative light scattering detector);

[0089] The degree of polarization is tested on an ultraviolet-visible spectrophotometer UV3600 (Shimadzu Corporation, Japan).

Preparation Example 1

[0090] cis-Polybutadiene: commercially available polybutadiene mass (purchased from Sichuan Petrochemical Ltd., 1,4-cis content ≥98%, and 2% 1,4-trans and the structure represented by Formula IV; the number average molecular weight M.sub.n=170,000) are cut into approximately 2 mm mass particles.

[0091] Epoxidation: Into a 250 ml three-neck flask equipped with a stirrer and a thermometer, 7 g of the above cis-polybutadiene mass particles and 100 ml of methylene chloride was added, the mass was dissolved and stirred under constant temperature in water bath at room temperature. Nitrogen gas was introduced for a few minutes when the mass was completely dissolved and became a sticky state. 9.90 g formic acid was added; 21.40 g 30% aqueous hydrogen peroxide solution was added dropwise with stirring; the reaction temperature was held for about 15 hours; according to .sup.1HNMR (CDCl.sub.3) analysis, the characteristic chemical shift peaks of 1,4-cis double bond disappeared (the characteristic chemical shift of the epoxy group δ=2.98, the characteristic chemical shift of 1,4-cis double bond δ=5.40). The reaction product is neutralized with 10% sodium carbonate solution to pH=7, the water phase was separated, the organic phase was washed and the phases were separated; absolute ethanol was added into the separated gel to precipitate, the precipitate was separated and washed with absolute ethanol once, waste liquid was filtered out to obtain a wet mass, which was dried at room temperature for 12 hours, and then dried in a vacuum oven at 40° C. for about 24 hours to constant weight to obtain 7.3 g of epoxidized butadiene rubber.

[0092] Hydrolysis: 1 g of the epoxidized butadiene rubber prepared above was weighted and dissolved in 100 ml of tetrahydrofuran, into which a solution of 5 ml water and 1 ml perchloric acid was added dropwise with stirring at 25° C. The addition was completed in 30 min and the stirring was continued at 25° C. for 12 hours. According to .sup.1HNMR (DMSO) analysis, the characteristic chemical shift peaks of the epoxidized butadiene rubber had disappeared (the characteristic chemical shift of the epoxy group, δ=2.98, the characteristic chemical shift of the adjacence dihydroxyls, δ=4.18). Sodium carbonate was added into the reaction solution for neutralization. 1000 ml of water was added into the reaction solution dropwise to precipitate; the precipitate was separated, into which 400 ml water was added and then soaked for 24 hours. The water was filtered out. The resulting polymer substance was dried for 24 hours at room temperature and then at 40° C. in a vacuum oven to constant weight. 1.12 g of solid matter was obtained. The molecular weight of the product was Mn=146,000, the molar content of adjacent dihydroxyl C4 units was 98%, its Tg value was 56° C.

Preparation Example 2

[0093] 2 g of the epoxidized butadiene rubber prepared as above was taken and dissolved in 200 ml of freshly distilled tetrahydrofuran, and then was added into a 500 ml stainless steel autoclave; 0.4 g Raney nickel (covered by ethanol, rinsed with tetrahydrofuran 3 times before being added into the reactor) was added. The autoclave was filled with nitrogen gas to a pressure of 1 MPa, then released to normal pressure; the nitrogen gas filling and pressure releasing were repeated 3 times. Hydrogen was introduced with stirring at 50° C. and pressurized to 1 MPa. The hydrogen pressure was held, and the reaction was carried out under stirring for 12 hours. .sup.1HNMR test was carried out, and the degree of epoxy group opening was about 75% (mol).

[0094] The reaction liquid was cooled to 0° C., and the pressure is released. The catalyst was filtered out. Into the reaction liquid without the catalyst, a solution formulated with 5 ml of water, 1 ml of perchloric acid, 5 ml of tetrahydrofuran was added dropwise within 30 mins; the reaction temperature was allowed to rise to 25° C., the temperature was held for 12 hours under stirring. According to .sup.1HNMR (DMSO) analysis, the characteristic chemical shift peaks of epoxidized butadiene rubber disappeared. 0.37 g of solid sodium carbonate was added into the reaction solution and stirred for 2 hours. Water was added dropwise into the reaction solution, and precipitate the precipitate; water was added for soaking 24 hours, then water was filtered out. The obtained polymer material was dried at room temperature for 24 hours, then dried to constant weight in a vacuum oven at 40° C. 2.35 g of milky white solid matter was obtained. Number average molecular weight is 133,000, the molar content of adjacent dihydroxyl C4 units is 24.7%, Tg value is 66° C.

Preparation Example 3

[0095] Styrene butadiene rubber: commercially available styrene butadiene rubber mass (Qilu Petrochemical Co., Ltd., styrene unit/butadiene unit (SB): 27/73, weight average molecular weight M.sub.w=320,000) was cut into approximately 2 mm rubber particles.

[0096] Epoxidation: into a 1000 ml three-neck flask equipped with a stirrer and a thermometer, 6 g of the above styrene butadiene rubber mass particles and 550 ml of toluene was added. The particles were dissolved and stirred under constant temperature in water bath at room temperature. Nitrogen was introduced for a few minutes when the mass was completely dissolved and became a sticky state. The mixture was heated to 40° C. and 3.0 g of formic acid was added, 8.2 g of 30% aqueous hydrogen peroxide solution was added dropwise with stirring; the reaction temperature was held for about 5 hours. According to .sup.1HNMR (CDCl.sub.3) analysis, the characteristic chemical shift peak of double bonds disappeared. The reaction product is neutralized with 10% sodium carbonate solution to pH=7; the water phase was separated. The remaining phase was washed and the liquid phases were separated. Absolute ethanol was added into the separated gel to precipitate; the precipitate was analyzed, which was washed with absolute ethanol once; waste liquid was filtered out to obtain wet gel, which was dried at room temperature for 12 h, and then in a vacuum oven at 40° C. for about 24 hours to constant weight. 6.33 g of epoxidized styrene butadiene rubber was obtained.

[0097] Hydrolysis: 1 g of the epoxidized styrene butadiene rubber as prepared above was taken and dissolved in 100 ml of tetrahydrofuran. A solution formulated with 5 ml of water and 1 ml of perchloric acid was added dropwise with stirring at 25° C. The addition was completed in 30 min and the stirring was continued at 25° C. for 12 hours. According to .sup.1HNMR (DMSO) analysis, the epoxy characteristic chemical shift peak disappeared. Sodium carbonate was added into the reaction solution for neutralization. 1000 ml water was added into the reaction solution dropwise to precipitate; the precipitate was separated, into which 500 ml water was added and soaked for 24 hours. Water was filtered out. The resulting polymer substance was dried for 24 hours at room temperature and at 40° C. in a vacuum oven to constant weight. 1.1 g white solid material was obtained, the proportion of adjacent dihydroxyl C4 units was found to be 62%.

Example 1

[0098] 1 g of translucent solids prepared according to the method of Preparation Example 1 and 1.1 g of elemental iodine particles were added together into a 20 ml glass flask, which was then sealed and stored at 50° C. for 24 hours, an iodine complex was obtained by gas-solid reaction. The iodine complex is black hard lumps with a weight of 2.0 g; a mass percentage of iodine in the iodine complex is 50%.

Example 2

[0099] 1 g of translucent solids prepared according to the method of Preparation Example 1 was dissolved in 20 ml dimethyl sulfoxide to form a dimethyl sulfoxide solution of the polymer; 1.1 g of elemental iodine particles was added at 25° C. and stirred, and the reaction liquid slowly turns brown due to the dissolution of iodine. After 2 hours, stirring was stopped, and the liquid-liquid homogeneous reaction completed. 200 ml of methanol was added, and a dark brown solid sticky mass precipitate. Such solid was dried under vacuum at 30° C. for 24 hours, and then 1.48 g black solid lump, which was the iodine complex of the present invention, the weight percentage of iodine in the iodine complex was 32%.

Example 3

[0100] 1 g of the translucent solid prepared by the method of Preparation Example 1 was added into a sealed glass bottle, then 20 ml of water and 2.0 g of elemental iodine were added, the elemental iodine dissolved in water was absorbed by the solid (that is, the liquid-solid reaction). The mixture was stirred at 25° C. for 8 hours; solid matter without dissolution and deformation was black. The solid material was taken out and dried under vacuum at 30° C. for 24 hours, and the weight was 1.21 g, which was the iodine complex of the present invention, the weight percentage of iodine in the iodine complex was 17.4%.

Example 4

[0101] Adsorption of Elemental Iodine Experiment:

[0102] Related substances: the solid products (particles with a size of about 3 mm) prepared according to the methods of Preparation Examples 1, 2 and 3, ethylene-vinyl alcohol polymer (EVOH, F171B, Kuraray Company, Japan, ethylene content 32%, particles with a size of about 3 mm), polyvinyl alcohol (PVA, Shanghai Chenqi Chemical Technology Co., Ltd., degree of polymerization of 1,680, degree of alcoholysis of 99%, molecular weight of 81,000, white powder), soluble starch of analytical pure grade were baked at 120° C. to constant weight before use.

[0103] 2 g (accuracy: 0.0001 g) of the above 6 kinds of solids was taken and put into 100 ml glass bottles, respectively. Then open vials containing 4 g (accuracy 0.0001 g) of elemental iodine were put into the above glass bottles, respectively, which were sealed and stood at 20° C. for 100 hours. The the solid materials were taken out and weighted to calculate the weight gain.

TABLE-US-00001 Mass percentage Weight Gain Weight gain ratio of iodine Substance (g) (%) .sup.a (%) Preparation 2.8 140 58 Example 1 Preparation 0.58 29 22.5 Example 2 Preparation 1.7 85 46.0 Example 3 EVOH 0.01 0.5 0.5 PVA 0.05 2.5 2.4 Soluble starch 0.48 24 19.4 .sup.a weight gain ratio = weight gain/weight of solid matter before absorbing iodine × 100%

Example 5

[0104] 1 g of the translucent solid obtained in Preparation Example 1 was dissolved in 20 ml of dimethyl sulfoxide, and the obtained solution is poured into a stainless steel tray (304 materials, 27×20×2 cm) to level naturally, and then was dried to constant weight to obtain a soft polymer film. The polymer film and iodine pellets were placed in a closed glass container under 50° C. for 12 hours, 1.2 g black complex film was obtained. The mass percentage of iodine in the iodine complex was 16.7%.

[0105] The iodine complex film obtained in Example 5 was scanned and imaged on XTH225 series industrial CT equipped with a 225 kV microfocus X-ray source. The results are shown in FIG. 1.

[0106] As can be seen from analysis of the IR analysis spectrum, as compared with the translucent solid prepared in Preparation Example 1, the peak of the stretching vibration of the hydroxyl groups of the iodine complex obtained in Example 5 gradually shifts to the direction of high wave number, which is the so-called blue shift, indicating the weakening of the hydroxyl hydrogen bond in the polymer structure, the lone pairs of electrons provided by the oxygen atoms in the two pairs of adjacent hydroxyl groups enter into the vacant valence electron orbital provided by iodine, form the iodine complex by way of coordination bond.

[0107] The iodine complex obtained in Example 5 was subjected to weight loss analysis. As shown in FIG. 2, as the temperature increasing, the iodine constantly dissociated and volatilized, and iodine volatilized completely at 350° C.

Example 6

[0108] For saline immersion test, the following materials were prepared:

[0109] the iodine complex as prepared in Example 1 (iodine content: 50.0%);

[0110] the starch bound with iodine as prepared in Example 4 (iodine content: 19.4%);

[0111] commercial povidone iodine solid (iodine content: 11.2%);

[0112] physiological saline prepared according to the standard method in Chinese Pharmacopoeia.

[0113] 1 g of the above substances were weighted accurately, and added into 100 ml physiological saline and soaked for 24 hours. The solid material was taken out, rinsed with a small amount of physiological saline, and the rinse liquid was combined with the soaking solution. The soaking liquid was titrated by using a sodium thiosulfate standard solution to calculate the iodine dissolution rate.

TABLE-US-00002 Iodine dissolution rate % = (iodine content in soaking solution in wt % × soaking solution weight)/Weight of iodine before soaking solids × 100. Iodine dissolution Substance Iodine wt % Soaked state rate (wt %) Example 1 50.0 No shape change of 0.24 solid Povidone iodine 11.2 Dissolved 100 Starch iodine complex 19.4 Dissolved 100

Example 7

[0114] The iodine-containing film prepared in Example 5 is cut into a 5 cm×4 cm piece with a thickness of 0.05-0.07 mm; then the piece was stretched on a stretching machine into a film with a thickness of 0.02 mm. The stretched iodine film was cut into two pieces of 2 cm×2 cm size, which were each loaded on a blank glass sheet (100% light transmittance). The transmittance Tsp (monomer transmittance, theoretical value is 50%), T⊥ (the orthogonal transmittance measured when the absorption axis of two polarizing films is placed vertically), T∥ (Parallel transmittance measured when the absorption axis of two polarizing films are placed in parallel) of the film were measured with an ultraviolet-visible spectrophotometer, and polarization degree of the film PE=(T∥−T⊥)/(T∥+T⊥)×100% was calculated. After testing and calculation, the degree of polarization is PE=90%. Referring to Example 6, the stretched iodine film was tested, it found that the iodine film soaked in physiological saline will not deform, and its iodine dissolution rate is 0.09 wt %; as compared with PVA with higher water solubility, the polarizing film prepared by the polymer provided by the present invention had better moisture resistance than the PVA polarizing film.

[0115] The embodiments of the present invention have been described above. However, this invention is not limited to the above embodiments. Any modification, equivalent replacements, or improvements made within the spirit and principle of the present invention shall be included in the protection scope of the present invention.