CN1252125C - Poly (2,2-dimethylene dioxy group-1, 3 propylene glycol carbonic ester), preparaton method and application - Google Patents
Poly (2,2-dimethylene dioxy group-1, 3 propylene glycol carbonic ester), preparaton method and application Download PDFInfo
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- CN1252125C CN1252125C CN 200410012905 CN200410012905A CN1252125C CN 1252125 C CN1252125 C CN 1252125C CN 200410012905 CN200410012905 CN 200410012905 CN 200410012905 A CN200410012905 A CN 200410012905A CN 1252125 C CN1252125 C CN 1252125C
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Abstract
The present invention relates to poly (2, 2-dimethylenedioxy-1, 3-propanediol carbonic ester) and a preparation method thereof. The ring-opening polymerization of the monomer of 2, 2-dimethylenedioxy-1, 3-propanediol carbonic ester is executed for preparing the poly((2, 2-dimethylenedioxy-1, 3-propanediol carbonic ester). The prepared polymer of the present invention is a novel aliphatic polycarbonate of which the main chain contains dihydroxy acetone structural units protected by ketal. The synthesized polycarbonate of the present invention has good biocompatibility and physical mechanical properties and can be further processed through functionalization, and is a novel biological degradable/absorbable aliphatic polycarbonate. Accordingly, the synthesized polycarbonate of the present invention has important practical significance in the fields of drug controlled release, in vivo material and tissue implantation engineering, gene therapy, etc.
Description
Technical field
Biodegradable/absorption the aliphatic polycarbonate that the present invention relates to a kind of novel structure promptly gathers (2,2-dimethylene two Oxy-1s, ammediol carbonic ether) and its production and use, belongs to chemical field.
Background technology
Aliphatic polycarbonate is the important biodegradable of a class/absorption polymer.It has excellent biological compatibility and physical and mechanical properties, and kind is a lot, Adjustable structure, and polymkeric substance has physics, chemistry and biology performance widely, can satisfy different needs; On the other hand, polycarbonate degraded back generates carbonic acid gas and neutral dibasic alcohol, the caused ill effect of carboxylic-acid substance that can avoid poly(lactic acid), polyglycolic acid etc. to produce in degradation process.Therefore, the biodegradable polycarbonate has obtained application more and more widely at aspects such as medicine sustained release, material implanted, organizational projects.
The synthetic polycondensation and the ring-opening polymerization two class polymerization processs of mainly containing of aliphatic polycarbonate.The former generally is difficult to obtain higher molecular weight.The latter except the polymkeric substance that can obtain higher molecular weight, can also with other cyclic monomer copolymerization, therefore just become one of synthesising biological degradable/high molecular most important method of absorption.Common PTMC, poly-(2,2-dimethyl trimethylene carbonate) etc. obtain by ring-opening polymerization.In order to further develop biodegradable/absorption polycarbonate, one of important approach is exactly the cyclic carbonate monomer of design and composite structure novelty.Cyclic carbonate monomer generally has five-membered ring and six membered ring, but more or less the carbonic acid gas phenomenon can take place during the ring-opening polymerization of five-membered ring carbonate monomer.Therefore people mainly use the six membered ring carbonate monomer to come synthetic fat adoption carbonic ether.
But contain functionalization side group polycarbonate monomer the practice on important meaning is arranged.It can get up medicine or other biological active substance by ring-opening polymerization and subsequent reactions by covalent bonds, form the polymer drug system; And by other modifications, can be so that polymer has physics, chemistry and biology performance widely, as improve the performances such as wetting ability, biocompatibility and biological degradation of polymkeric substance, to satisfy different needs.At present but the synthetic of functional poly carbonic ether is subjected to people's attention just day by day with applied research, contains sugared structural unit and introduces all kinds such as the polycarbonate of functionalization side groups such as hydroxyl, amino, ester group, carboxylic acid but people have synthesized main chain.But the molecular weight of these polymkeric substance generally can be too not high, and second-order transition temperature is not high yet, and mechanical and physical performance and biocompatibility all are worth improving.
Therefore, people wait in expectation novel structure, have better biocompatibility, better wetting ability, better physical and mechanical properties and than the polycarbonate that contains other functional groups of high glass transition temperature.The object of the invention just is the polycarbonate that provides such.
The present invention has carried out deep research for achieving the above object to this compounds.Found that the otan with the ketal protection is that the unitary polycarbonate of backbone structure has better biocompatibility, better wetting ability, better physical and mechanical properties and higher second-order transition temperature, thereby finished the present invention.
Summary of the invention
The invention provides poly-(2,2-dimethylene two Oxy-1s, ammediol carbonic ether), its structural formula:
Above-mentioned polymkeric substance is unbodied white solid, or the rubber-like solid, and number-average molecular weight is 1.2-13 * 10
4, polydispersity is 1.1-1.9; Its second-order transition temperature is 49 ℃ (Mn is 5.5 ten thousand).Its structure is through infrared spectra (FTIR), hydrogen nuclear magnetic resonance spectrum (
1HNMR) and nuclear magnetic resonance of carbon spectrum (
13CNMR) confirm.The mensuration of number-average molecular weight and polydispersity is measured by gel chromatography GPC, and thermal property is measured and characterized by differential scanning calorimetry (DSC).
The present invention also provides the preparation method of poly-(2,2-dimethylene two Oxy-1s, ammediol carbonic ether).With 2,2-dimethylene two Oxy-1s, ammediol carbonate monomer make poly-(2,2-dimethylene two Oxy-1s, ammediol carbonic ether) through the body ring-opening polymerization in the presence of aluminum alkoxide, stannous octoate catalyst.
Catalyzer and monomeric molar ratio are 1 in above-mentioned polyreaction: 500-2000; 8-48 hour ring-opening polymerization time.
Used monomer 2 in above-mentioned polyreaction, 2-dimethylene two Oxy-1s, the ammediol carbonic ether is with 1, ring closure reaction takes place with the phosgene derivative and makes in 3-dioxolane-2,2-dimethanol in the presence of alkali.
The phosgene derivative is preferably Vinyl chloroformate in above-mentioned ring closure reaction, and alkali is triethylamine, and solvent is a tetrahydrofuran (THF), and temperature is-10-25 ℃.
The phosgene derivative is preferably triphosgene in above-mentioned ring closure reaction, and alkali is pyridine, and solvent is methylene dichloride and trichloromethane, and temperature is 20-40 ℃.
Used 1 in above-mentioned ring closure reaction, 3-dioxolane-2, the 2-dimethanol reduces 1 by lithium aluminium hydride in ether or tetrahydrofuran (THF), 3-dioxolane-2,2-dioctyl phthalate ethyl ester makes.
Adopt the beneficial effect that the present invention reached:
Poly-(2 of gained of the present invention; 2-dimethylene two Oxy-1s; the ammediol carbonic ether) be that a kind of novel principal chain of synthetic contains the aliphatic polycarbonate of the otan structural unit of ketal protection first, this is a kind of novel biodegradable/absorption polycarbonate.Because this polymkeric substance is to be made by the otan derivative, its degraded product is an otan, and it is one of product of human body intracellular metabolic, so this polycarbonate has low toxicity, and excellent biological compatibility is arranged; Owing to introduce 5 yuan of rings 1 of inflexible, 3-dioxolane side group, its second-order transition temperature improves (from-18 ℃ of 49 ℃ of bringing up to this polymkeric substance of PTMC) and improves its physical and mechanical properties, make simultaneously wetting ability increase again, degradation rate wants fast than poly-(2,2-dimethyl trimethylene carbonate); Owing to can obtain containing the polycarbonate of ketone carbonyl through follow-up deprotection reaction; further functionalization also; or directly combine, so important practice significance is arranged in fields such as medicine sustained release, material implanted, organizational project and gene therapies with containing amino bioactive molecules such as materials such as medicine, enzyme.
Poly-(2,2-dimethylene two Oxy-1s, ammediol carbonic ether) of gained of the present invention have following purposes:
1. improve the biocompatibility of polycarbonate, thereby be applicable to biological medical polymer material.
2. improve the physical and mechanical properties of polycarbonate, improve its second-order transition temperature, can be used for organizational project.
3. improve the wetting ability of polycarbonate, improve its degradation rate, can be used for controlled drug delivery system.
4. further deprotection, further functionalization can be used for polymer drug.
Description of drawings
Fig. 1 is the vitro cytotoxicity figure of poly-(2,2-dimethylene two Oxy-1s, ammediol carbonic ether) of the present invention;
Fig. 2 is the external degradation figure of poly-(2,2-dimethylene two Oxy-1s, ammediol carbonic ether) of the present invention.
Embodiment:
The invention will be further described below in conjunction with example;
Example one:
1,3-dioxolane-2, the preparation of 2-dimethanol: under the room temperature, in argon gas atmosphere, in 300 milliliters of anhydrous tetrahydrofuran (THF) suspension that contain 11.88 gram (0.31 mole) lithium aluminium hydride, slowly add (be preferably in 2 hours and add) and contain 50.0 gram (0.23 moles) 1,3-dioxolane-2,200 milliliters tetrahydrofuran solution of 2-dicarboxylate, and then reacted 2 hours, the ethyl acetate that adds 50 milliliters is with the lithium aluminium hydride of decomposing excessive, add 50 ml waters again, continue reaction 2 hours.Filter, wash solids 3 times with 100 milliliters of tetrahydrofuran (THF)s, gained filtrate is used anhydrous sodium sulfate drying, the pressure reducing and steaming solvent, the debris underpressure distillation, the cut of 130-2 ℃/35Pa of collection gets the colourless or light yellow viscous liquid 1 of 22.54 grams, 3-dioxolane-2,2-dimethanol, productive rate are 73%.
2,2-dimethylene two Oxy-1s, the preparation of ammediol carbonic ether: in the time of 0 ℃, to containing 13.40 gram (0.1 moles) 1,3-dioxolane-2, slowly add 50 milliliters the anhydrous tetrahydro furan mixed solution that (be preferably in 1.5 hours and add) contains 22.6 gram (0.1 mole) triethylamines in 500 milliliters the anhydrous tetrahydro furan mixed solution of 2-dimethanol and 22.80 gram (0.21 mole) Vinyl chloroformates, continue reaction 2 hours in room temperature then.Reaction finishes after-filtration, and filtrate concentrating obtains
Residue, obtain white needle-like crystals with re-crystallizing in ethyl acetate again, productive rate 47%.Fusing point is 96-97 ℃ of .FTIR (KBr): 1751.9 (vs, C=O), 1183.8,1095.7,1131.3cm
-1(vs, C-O-C).
1H NMR (CDCl
3): δ=4.239 (4H, s, CH
2OCOCH
2), 4.049 (4H, s, OCH
2CH
2O).
13C NMR (CDCl
3): δ=147.136 (C=O), 99.474 (season C), 70.730 (CH
2OCOCH
2), 64.898 (OCH
2CH
2O).
Example two:
Poly-(2,2-dimethylene two Oxy-1s, the ammediol carbonic ether) preparation: with 2 of 0.3203g, 2-dimethylene two Oxy-1s, the anhydrous toluene solution of the stannous iso caprylate of 0.1 mol of ammediol carbonate monomer and 20 microlitres is transferred in the exsiccant polymerizing pipe of magneton successively, decompression is taken out and is desolvated, feed argon gas, three times so repeatedly, tube sealing under high vacuum places polymerizing pipe the oil bath that is heated to 110 ℃ in advance to react 24 hours, finishes the back and add 2 milliliters of methylene dichloride dissolve polymers in polymerizing pipe, with 40 ml methanol reprecipitations, resulting polymers was 40 ℃ of following vacuum-dryings 24 hours.Productive rate is 91.1%, and number-average molecular weight is 44200, and polydispersity is 1.81.IR (KBr): 1758.7cm
-1(vs, C=O), 1255.3cm
-1, 1181.9cm
-1, 1043.0cm
-1(vs, C-O-C);
1HNMR (300MHz): 4.181ppm (4H, s, CH
2OCOCH
2), 4.012ppm (4H, s, OCH
2CH
2O);
13CNMR (300MHz): 153.120ppm (C=O), 104.601ppm (season C), 66.242ppm (CH
2OCOCH
2), 65.420ppm (OCH
2CH
2O).
Example three:
Poly-(2,2-dimethylene two Oxy-1s, the ammediol carbonic ether) preparation: with 2 of 0.3203g, 2-dimethylene two Oxy-1s, the anhydrous toluene solution of the stannous iso caprylate of 0.1 mol of ammediol carbonate monomer and 10 microlitres is transferred in the exsiccant polymerizing pipe of magneton successively, decompression is taken out and is desolvated, feed argon gas, three times so repeatedly, tube sealing under high vacuum places polymerizing pipe the oil bath that is heated to 110 ℃ in advance to react 24 hours, finishes the back and add 2 milliliters of methylene dichloride dissolve polymers in polymerizing pipe, with 40 ml methanol reprecipitations, resulting polymers was 40 ℃ of following vacuum-dryings 24 hours.Productive rate is 84.3%, and number-average molecular weight is 42400, and polydispersity is 1.48.
Example four:
Poly-(2,2-dimethylene two Oxy-1s, the ammediol carbonic ether) preparation: with 2 of 0.3203g, 2-dimethylene two Oxy-1s, the anhydrous toluene solution of the stannous iso caprylate of 0.1 mol of ammediol carbonate monomer and 40 microlitres is transferred in the exsiccant polymerizing pipe of magneton successively, decompression is taken out and is desolvated, feed argon gas, three times so repeatedly, tube sealing under high vacuum places polymerizing pipe the oil bath that is heated to 110 ℃ in advance to react 24 hours, finishes the back and add 2 milliliters of methylene dichloride dissolve polymers in polymerizing pipe, with 40 ml methanol reprecipitations, resulting polymers was 40 ℃ of following vacuum-dryings 24 hours.Productive rate is 85.0%, and number-average molecular weight is 39200, and polydispersity is 1.75.
Example five:
Poly-(2,2-dimethylene two Oxy-1s, the ammediol carbonic ether) preparation: with 2 of 0.3203g, 2-dimethylene two Oxy-1s, the anhydrous toluene solution of the stannous iso caprylate of 0.1 mol of ammediol carbonate monomer and 20 microlitres is transferred in the exsiccant polymerizing pipe of magneton successively, decompression is taken out and is desolvated, feed argon gas, three times so repeatedly, tube sealing under high vacuum places polymerizing pipe the oil bath that is heated to 110 ℃ in advance to react 48 hours, finishes the back and add 2 milliliters of methylene dichloride dissolve polymers in polymerizing pipe, with 40 ml methanol reprecipitations, resulting polymers was 40 ℃ of following vacuum-dryings 24 hours.Productive rate is 83.5%, and number-average molecular weight is 46800, and polydispersity is 1.69.
Example six:
Poly-(2,2-dimethylene two Oxy-1s, the ammediol carbonic ether) preparation: with 2 of 0.3203g, 2-dimethylene two Oxy-1s, the anhydrous toluene solution of the stannous iso caprylate of 0.1 mol of ammediol carbonate monomer and 20 microlitres is transferred in the exsiccant polymerizing pipe of magneton successively, decompression is taken out and is desolvated, feed argon gas, three times so repeatedly, tube sealing under high vacuum places polymerizing pipe the oil bath that is heated to 110 ℃ in advance to react 36 hours, finishes the back and add 2 milliliters of methylene dichloride dissolve polymers in polymerizing pipe, with 40 ml methanol reprecipitations, resulting polymers was 40 ℃ of following vacuum-dryings 24 hours.Productive rate is 82.1%, and number-average molecular weight is 53700, and polydispersity is 1.54.
Example seven:
Poly-(2,2-dimethylene two Oxy-1s, the ammediol carbonic ether) preparation: with 2 of 0.3203g, 2-dimethylene two Oxy-1s, the anhydrous toluene solution of the stannous iso caprylate of 0.1 mol of ammediol carbonate monomer and 20 microlitres is transferred in the exsiccant polymerizing pipe of magneton successively, decompression is taken out and is desolvated, feed argon gas, three times so repeatedly, tube sealing under high vacuum places polymerizing pipe the oil bath that is heated to 110 ℃ in advance to react 12 hours, finishes the back and add 2 milliliters of methylene dichloride dissolve polymers in polymerizing pipe, with 40 ml methanol reprecipitations, resulting polymers was 40 ℃ of following vacuum-dryings 24 hours.Productive rate is 92.6%, and number-average molecular weight is 55000, and polydispersity is 1.46.
Example eight:
Poly-(2,2-dimethylene two Oxy-1s, the ammediol carbonic ether) preparation: with 2 of 0.3203g, 2-dimethylene two Oxy-1s, the anhydrous toluene solution of the stannous iso caprylate of 0.1 mol of ammediol carbonate monomer and 20 microlitres is transferred in the exsiccant polymerizing pipe of magneton successively, decompression is taken out and is desolvated, feed argon gas, three times so repeatedly, tube sealing under high vacuum places polymerizing pipe the oil bath that is heated to 100 ℃ in advance to react 24 hours, finishes the back and add 2 milliliters of methylene dichloride dissolve polymers in polymerizing pipe, with 40 ml methanol reprecipitations, resulting polymers was 40 ℃ of following vacuum-dryings 24 hours.Productive rate is 82.5%, and number-average molecular weight is 54500, and polydispersity is 1.39.
Example nine:
Poly-(2,2-dimethylene two Oxy-1s, the ammediol carbonic ether) preparation: with 2 of 0.3203g, 2-dimethylene two Oxy-1s, the anhydrous toluene solution of the stannous iso caprylate of 0.1 mol of ammediol carbonate monomer and 20 microlitres is transferred in the exsiccant polymerizing pipe of magneton successively, decompression is taken out and is desolvated, feed argon gas, three times so repeatedly, tube sealing under high vacuum places polymerizing pipe the oil bath that is heated to 120 ℃ in advance to react 24 hours, finishes the back and add 2 milliliters of methylene dichloride dissolve polymers in polymerizing pipe, with 40 ml methanol reprecipitations, resulting polymers was 40 ℃ of following vacuum-dryings 24 hours.Productive rate is 84.8%, and number-average molecular weight is 48900, and polydispersity is 1.59.
Example ten:
Poly-(2,2-dimethylene two Oxy-1s, the ammediol carbonic ether) preparation: with 2 of 0.3203g, 2-dimethylene two Oxy-1s, the anhydrous toluene solution of the stannous iso caprylate of 0.1 mol of ammediol carbonate monomer and 20 microlitres is transferred in the exsiccant polymerizing pipe of magneton successively, decompression is taken out and is desolvated, feed argon gas, three times so repeatedly, tube sealing under high vacuum places polymerizing pipe the oil bath that is heated to 140 ℃ in advance to react 24 hours, finishes the back and add 2 milliliters of methylene dichloride dissolve polymers in polymerizing pipe, with 40 ml methanol reprecipitations, resulting polymers was 40 ℃ of following vacuum-dryings 24 hours.Productive rate is 79.3%, and number-average molecular weight is 31900, and polydispersity is 1.67.
Example 11:
Poly-(2,2-dimethylene two Oxy-1s, the ammediol carbonic ether) preparation: with 2 of 0.3203g, 2-dimethylene two Oxy-1s, the anhydrous toluene solution of the triisobutyl aluminium of 0.1 mol of ammediol carbonate monomer and 20 microlitres is transferred in the exsiccant polymerizing pipe of magneton successively, decompression is taken out and is desolvated, feed argon gas, three times so repeatedly, tube sealing under high vacuum places polymerizing pipe the oil bath that is heated to 110 ℃ in advance to react 24 hours, finishes the back and add 2 milliliters of methylene dichloride dissolve polymers in polymerizing pipe, with 40 milliliters of ether reprecipitations, resulting polymers was 40 ℃ of following vacuum-dryings 24 hours.Productive rate is 48.3%, and number-average molecular weight is 20900, and polydispersity is 1.29.
Example 12:
Poly-(2,2-dimethylene two Oxy-1s, the ammediol carbonic ether) preparation: with 2 of 0.3203g, 2-dimethylene two Oxy-1s, the anhydrous toluene solution of the triisobutyl aluminium of 0.1 mol of ammediol carbonate monomer and 40 microlitres is transferred in the exsiccant polymerizing pipe of magneton successively, decompression is taken out and is desolvated, feed argon gas, three times so repeatedly, tube sealing under high vacuum places polymerizing pipe the oil bath that is heated to 110 ℃ in advance to react 24 hours, finishes the back and add 2 milliliters of methylene dichloride dissolve polymers in polymerizing pipe, with 40 milliliters of ether reprecipitations, resulting polymers was 40 ℃ of following vacuum-dryings 24 hours.Productive rate is 54.3%, and number-average molecular weight is 14700, and polydispersity is 1.38.
Example 13:
Poly-(2,2-dimethylene two Oxy-1s, the ammediol carbonic ether) vitro cytotoxicity: adopt MTT method test poly-(2,2-dimethylene two Oxy-1s, the ammediol carbonic ether) vitro cytotoxicity, earlier 5 generation COS7 cell kinds in culture plate, 2000 in every hole, 37 degree cultivations 48 hours.Prepare the dimethyl sulfoxide solution of 20 mg/ml again, use the methyl-sulphoxide gradient dilution, use substratum DMEM (containing 10%FBS) dilution then, polymers soln (is used poly-(lactic acid-ethanol) (75: 25) sample and blank in contrast, wherein poly-(lactic acid-ethanol) (75: 25) sample is the macromolecular material that can be used for human body through the FDA approval) be added in the Tissue Culture Plate, every hole adds 10 microlitres, finally reaches predetermined concentration, continues to cultivate 24 hours.Add MTT, add SDS again, cultivated again 24 hours.Be that the 550nm place measures absorbancy with Bio-Rad 550 microplate reader at wavelength at last, and be reference wavelength with 650nm.The cytotoxicity of polymkeric substance is represented with the cell survival rate of COS7.The result as shown in Figure 1.The cell survival rate of poly-(lactic acid-ethanol) (75: 25) of curve 1 representative sample is with concentration curve among the figure, and the cell survival rate of poly-(2,2-dimethylene two Oxy-1s, the ammediol carbonic ether) sample of curve 2 representatives is with concentration curve.The result shows that poly-(2,2-dimethylene two Oxy-1s, ammediol carbonic ether) sample cell toxicity of gained of the present invention is higher slightly than poly-(lactic acid-ethanol) (75: 25) sample, but cytotoxicity is still lower.
Poly-(2,2-dimethylene two Oxy-1s, the ammediol carbonic ether) external degradation: the polymkeric substance of getting 100 milligrams is dissolved in 4 milliliters methylene dichloride, on the silanized glass plate, be equipped with polymeric film with solvent evaporates film forming legal system, after the vacuum-drying 24, get about 50 milligrams polymeric film and place 20 milliliters of phosphate buffer solution (pH=7.4,0.1M) at 37 ℃ of isothermal vibrations, take out sample at regular intervals, washing, drying is weighed, and calculates rate of weight loss and measures its change of molecular weight with GPC, and the result as shown in Figure 2.Curve shows that rate of weight loss was with the degradation time change curve when water of poly-(2,2-dimethylene two Oxy-1s, ammediol carbonic ether) sample was degraded among the figure.The result shows that this polymer degradation is slower.The preceding number-average molecular weight Mn of degraded is 58900, and number-average molecular weights are 58100 after 4 weeks of degraded, and rate of weight loss is 1.39%, and number-average molecular weight is 57900 after 12 weeks of degrading, and rate of weight loss is 7.72%.Because number-average molecular weight changes little, therefore poly-(2,2-dimethylene two Oxy-1s, ammediol carbonic ether) degraded (PEOPDC) is a kind of surface erosion process.
Poly-(2,2-dimethylene two Oxy-1s, ammediol carbonic ether) are a kind of novel biodegradable/absorption polycarbonate.Have low toxicity, excellent biological compatibility is arranged; Owing to introduce 5 yuan of rings 1 of inflexible, 3-dioxolane side group, its second-order transition temperature improves (from-18 ℃ of 49 ℃ of bringing up to this polymkeric substance of PTMC) and improves its physical and mechanical properties, make simultaneously wetting ability increase again, degradation rate wants fast than poly-(2,2-dimethyl trimethylene carbonate); Owing to can obtain containing the polycarbonate of ketone carbonyl through follow-up deprotection reaction, further functionalization also, so important application prospects is arranged in fields such as medicine sustained release, material implanted, organizational project and gene therapies.
Claims (4)
1. poly-(2,2-dimethylene two Oxy-1s, ammediol carbonic ether), its number-average molecular weight is 1.2-13 * 10
4, structural formula:
2. claim 1 described poly-(2,2-dimethylene two Oxy-1s, the ammediol carbonic ether) preparation method, it is characterized in that: with 1,3-dioxolane-2, the 2-dimethanol with the phosgene derivative in the presence of alkali ,-ring closure reaction takes place and makes monomer 2,2-dimethylene two Oxy-1s, ammediol carbonic ether in 10-25 ℃; With 2, ring-opening polymerization takes place and makes poly-(2,2-dimethylene two Oxy-1s, ammediol carbonic ether) in 2-dimethylene two Oxy-1s, ammediol carbonate monomer in the presence of metal-based catalyst; Ring-opening polymerization carries out in the mode of mass polymerization, and mass polymerization is carried out under temperature is 100-140 ℃, argon shield; Catalyzer and monomeric molar ratio are 1: 500-2000,8-48 hour ring-opening polymerization time.
3. method according to claim 2 is characterized in that: metal-based catalyst is stannous iso caprylate or aluminum isopropylate.
Claim 1 described poly-(2,2-dimethylene two Oxy-1s, ammediol carbonic ether) but as the application of biodegradable/absorbing material in medicine sustained release or field of tissue engineering technology of functionalization.
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