CN109912790A - A kind of modified polycarbonate with highly blood coagulation resistant - Google Patents
A kind of modified polycarbonate with highly blood coagulation resistant Download PDFInfo
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- CN109912790A CN109912790A CN201910161614.0A CN201910161614A CN109912790A CN 109912790 A CN109912790 A CN 109912790A CN 201910161614 A CN201910161614 A CN 201910161614A CN 109912790 A CN109912790 A CN 109912790A
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- blood coagulation
- ketone
- dioxanes
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- polycarbonate
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- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 29
- 239000004417 polycarbonate Substances 0.000 title claims abstract description 29
- 230000023555 blood coagulation Effects 0.000 title claims abstract description 18
- 229920000642 polymer Polymers 0.000 claims abstract description 15
- 229920001577 copolymer Polymers 0.000 claims abstract description 11
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims abstract description 11
- NJNWCIAPVGRBHO-UHFFFAOYSA-N 2-hydroxyethyl-dimethyl-[(oxo-$l^{5}-phosphanylidyne)methyl]azanium Chemical group OCC[N+](C)(C)C#P=O NJNWCIAPVGRBHO-UHFFFAOYSA-N 0.000 claims abstract description 7
- YHHSONZFOIEMCP-UHFFFAOYSA-O phosphocholine Chemical compound C[N+](C)(C)CCOP(O)(O)=O YHHSONZFOIEMCP-UHFFFAOYSA-O 0.000 claims abstract description 7
- 229950004354 phosphorylcholine Drugs 0.000 claims abstract description 7
- 238000007306 functionalization reaction Methods 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims abstract description 6
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 4
- -1 5- methacryloxymethyl -1,3- dioxanes Chemical class 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- QNNJNFZIZKNMOS-UHFFFAOYSA-N 1,3-dioxan-5-yl prop-2-enoate Chemical class C=CC(=O)OC1COCOC1 QNNJNFZIZKNMOS-UHFFFAOYSA-N 0.000 claims description 2
- MYPXHUMQQISEBF-UHFFFAOYSA-N 1,3-dioxan-5-ylmethyl prop-2-enoate Chemical class C=CC(=O)OCC1COCOC1 MYPXHUMQQISEBF-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 2
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 claims description 2
- 229960002317 succinimide Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 18
- 239000000463 material Substances 0.000 abstract description 9
- 230000010100 anticoagulation Effects 0.000 abstract description 2
- 229920002521 macromolecule Polymers 0.000 abstract description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 13
- 210000001772 blood platelet Anatomy 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 239000000178 monomer Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 230000002429 anti-coagulating effect Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 229920005604 random copolymer Polymers 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000000017 hydrogel Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 210000001243 pseudopodia Anatomy 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 230000010148 water-pollination Effects 0.000 description 2
- 229910000619 316 stainless steel Inorganic materials 0.000 description 1
- OPDIIQCYLFZJGS-UHFFFAOYSA-N C(=O)=C1OCCCO1 Chemical class C(=O)=C1OCCCO1 OPDIIQCYLFZJGS-UHFFFAOYSA-N 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003519 biomedical and dental material Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000006177 thiolation reaction Methods 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Materials For Medical Uses (AREA)
Abstract
The invention discloses a kind of modified polycarbonates with highly blood coagulation resistant.For linear macromolecule polymer, polymer lateral chain contain can functionalization double bond and contain hydrophilic Phosphorylcholine group.Including copolymer A, B and C.Its preparation process are as follows: be first copolymerized by trimethylene carbonate (TMC) and trimethylene derivative, 2- methylacryoyloxyethyl Phosphorylcholine (MPC) is then grafted on copolymer side chain by two mercaptan and the reaction of the click chemistry of double bond and obtains the modified polycarbonate that target product has highly blood coagulation resistant.There is the present invention modified polycarbonate of highly blood coagulation resistant can change the performance of polycarbonate by adjusting monomeric species and ratio and the amount of side chain Phosphorylcholine group, improve anticoagulation ability of the polycarbonate as biodegradable medical macromolecular materials；Double bond on its side chain can provide reaction site for subsequent grafting large biological molecule or other function molecule, and research potential is big, and derivative performance is wide.
Description
Technical field
The present invention relates to biomedical engineering functional material technical field of modification, more particularly, to a kind of changing for polycarbonate
Property.
Background technique
Biodegradable aliphatic polycarbonate has good biological degradability, excellent biocompatibility and physical machine
Tool performance is a kind of important biodegradable medical macromolecular materials, oneself is in hypodermal contraception implants, three-dimensional tissue's engineering branch
The fields such as frame, neural restoration and drug controlled release show greatly application and potentiality.Most common and wide research can
Biodegradable aliphatic polycarbonates are polytrimethylene carbonate (PTMC), a kind of amorphous state or with crystallizing a little
Polycarbonate, glass transition temperature be about -17 DEG C, room temperature and in vivo under the conditions of have good elasticity.Meanwhile
PTMC degradation in vivo will not release acid and cause acid rise in part and the degradation behavior automatically speeded up be caused to occur,
And its degradation model is surface erosion, and during degradation, although material is weightless, molecular weight is held essentially constant, thus
It is set to be always maintained at higher mechanical property during degradation.But there is no functional groups, material on the main chain of PTMC
The disadvantages of surface hydrophilicity is weak and cannot be grafted drug or other function substance, is limiting its popularization.Fredrik
Nederberg et al. (Organo Hydrogel Hybrids.Formation of Reservoirs for
ProteinDelivery [J] .Biomacromolecules, 2005,6 (6): 3088-3094.) by hydrophobic PTMC
It is modified, the PTMC blocked with hydrophily Phosphorylcholine group (PC) has been synthesized, a kind of biodegradable organic water-setting has been made
Glue hybrid material.This hydrogel hybrid material is to have synthesized hydroxy-end capped PTMC first, so using 1,4-butanediol as initiator
The PTMC of Phosphorylcholine sealing end is synthesized by the chloro- 2- oxygen -1,3,2- dioxaphospholane of 2- afterwards.It will be apparent that poly- for this
It closes for object, has on a polymer chain and most only there are two Phosphorylcholine group, so low PC grafting rate is unsatisfactory for it
As bio-medical material for clinical use.And do not have on polymer chain other can functionalization group, cannot be subsequent
It is grafted large biological molecule or other function molecule provides reaction site.Therefore it is big to need to prepare a kind of research potential, it is derivative
The wide modified polycarbonate with highly blood coagulation resistant of energy.
Summary of the invention
The purpose of the present invention is to provide a kind of synthesis is simple, without being protected and being deprotected to functional group, can be again
The bionical polycarbonate of the better phosphatide of functionalization, biocompatibility.Its technical solution is: a kind of with highly blood coagulation resistant
Modified polycarbonate is linear carbonate polymer comprising main chain, and side chain includes can functionalization double bond and hydrophilic
Phosphorylcholine group has following monomer structure, including copolymer A, B and C:
Its preparation process are as follows: be first copolymerized by trimethylene carbonate (TMC) and trimethylene derivative, then pass through two sulphur
The click chemistry of pure and mild double bond reacts grafting 2- methylacryoyloxyethyl Phosphorylcholine (MPC) on copolymer side chain and obtains mesh
Mark the modified polycarbonate that product has highly blood coagulation resistant.
The trimethylene derivative includes: 5- methyl -5- allyloxy carbonyl -1,3- dioxanes -2- ketone, 5- allyl oxygen
Base carbonyl -1,3- dioxanes -2- ketone or 5- acryloyloxymethyl -1,3- dioxanes -2- ketone or 5- methacryloxymethyl -
1,3- dioxanes -2- ketone or 5- acryloyl-oxy -1,3- dioxanes -2- ketone or 5- methacryloxypropyl -1,3- dioxanes -2-
Ketone.
Two mercaptan includes: 1,2- dithioglycol, 1,3- dimercaptopropane and 1,4- succinimide mercaptans.
Its synthesis step includes synthesizing a cyclic carbonate monomer containing alkene first, then the novel cyclic carbonic acid
Ester monomer contains alkene copolymer at side chain with trimethylene carbonate ring-opening polymerisation by a certain percentage, to introduce in the side chain double
The click chemistry reaction of key, mercaptan and double bond finally by both ends with sulfydryl has hydrophily in side chain graft containing alkene copolymer
MPC.
The beneficial effects of the present invention are:
1) main polymer chain is linear macromolecule polyalcohol, has good elasticity.The polymer can pass through
It adjusts monomeric species and ratio and the amount of side chain Phosphorylcholine group changes the performance of polycarbonate, improve polycarbonate and make
For the anticoagulation ability of biodegradable medical macromolecular materials；Double bond on the polymer lateral chain can be big for subsequent grafting biology
Molecule or other function molecule provide reaction site, and research potential is big, and derivative performance is wide.
2) the bionical carbonate polymer of phosphatide has outstanding anticoagulant effect, biology compared with the PTMC before modification
Compatibility is more preferable.
Detailed description of the invention
Fig. 1 has the modified polycarbonate A (R=CH of highly blood coagulation resistant3, n=0) coating surface platelet adhesion reaction
The fluorogram of 45min.Wherein, SS:316 stainless steel；PTMC: polytrimethylene carbonate；PTMMAC:TMC's and MAC is random total
Polymers；A (R=CH3, n=0): the PTMMAC of Phosphorylcholine base group modification.
Fig. 2 has the modified polycarbonate A (R=CH of highly blood coagulation resistant3, n=0) coating surface platelet adhesion reaction
The SEM electron microscope of 45min.
Trimethylene derivatives monomer structural formula used in Fig. 3.
Specific embodiment
Embodiment 1
A.5- the synthesis of methyl -5- allyloxy carbonyl -1,3- dioxanes -2- ketone (MAC)
It is the evil of Material synthesis 5- methyl -5- allyloxy carbonyl -1,3- two with 2,2- (double methylols) propionic acid (bis-HPA)
Alkane -2- ketone (MAC).This monomer for the side chain of polycarbonate provide can functionalization double bond.
The preparation of b.TMC and MAC random copolymer
It weighs a certain amount of TMC and MAC monomer (molar ratio 3:1) and a clean and dry magnetic stirrer is placed in
In the single-necked flask of the special drying sealed with rubber stopper, reaction unit with oil pump take out half an hour vacuum after, respectively
Catalyst and initiator are dissolved in dry n-hexane and diluting, and stannous octoate (4 × 10 is added by every mole of monomer with syringe- 4Mol catalyst), n-octyl alcohol (2 × 10-5Mol initiator) be injected into reaction unit after, extract syringe, with vacuum ester seal,
Continue after vacuumizing a hour, stop vacuumizing, seals.Then, reaction unit, which is placed in oil bath pan, is warming up to 115 DEG C, instead
Answer 12h.After reaction, it is cooled to room temperature, after dissolving polymer with chloroform, sedimentation is added dropwise into cold alcohol solvent for solution,
Product vacuum is dry, obtains copolymer and is named as PTMMAC.(the practical ratio of components of copolymer is TMC:MAC=2.08:1.Divide equally again
Son amount Mw=81.9KD)
C. the preparation of Thiolation -2- methylacryoyloxyethyl Phosphorylcholine (ETPC)
1,2- dithioglycol (9.42g, 100mmol) and 2- methylacryoyloxyethyl Phosphorylcholine (MPC) (14.76g,
50mmol) be placed in 250ml single-necked flask, be added 100ml chloroform (solvent), then be added diisopropylamine (278.8uL,
Alkaline environment 2.0mmol) is provided, is placed in oil bath pan and is warming up to 25 DEG C, reaction for 24 hours, after reaction, is settled with acetone, is led to
Column Chromatographic purification product is crossed, then is dried in vacuo, ETPC obtained.
D. with the modified polycarbonate A (R=CH of highly blood coagulation resistant3, n=0) preparation
Reaction dissolvent 300ml (chloroform: anhydrous second is added in ETPC (0.42g, 1mmol) and PTMMAC (5g, 0.06mmol)
Alcohol (5:1)), then be added diisopropylamine (29.5ul, 0.21mmol) provide alkaline environment, 25 DEG C of reaction temperature, the reaction time
For 24 hours, after reaction, solution is concentrated, cold ethyl alcohol sedimentation, and product vacuum is dry.Obtain target product A (R=CH3, n=0).
(MPC grafting rate=side chain structural unit containing MPC amount/total structural unit amount=1.8% of polymer)
After tested: target product has excellent anticoagulant effect.
It is described further in conjunction with attached drawing 1 and Fig. 2 as follows:
There is the modified polycarbonate A (R=CH of highly blood coagulation resistant in conjunction with attached drawing 13, n=0) coating surface blood platelet it is viscous
As can be seen that A (R=CH in the fluorogram of attached 45min3, n=0) coating surface platelet adhesion reaction quantity far less than SS,
The platelet adhesion reaction quantity on the surface PTMC and PTMMAC.
There is the modified polycarbonate A (R=CH of highly blood coagulation resistant in conjunction with attached drawing 23, n=0) coating surface blood platelet it is viscous
In the SEM electron microscope of the attached 45min as can be seen that surface SS, platelet aggregation and activation degree are the most serious；PTMC coating surface
There are the aggregation and activation of most of blood platelet；Most of blood platelet of PTMMAC coating surface has also stretched out pseudopodium；And there is height
Modified polycarbonate A (the R=CH of anticoagulant property3, n=0) coating surface blood platelet at normal plate-like, do not extend out pseudopodium more
Do not occur assembling and being activated.
Therefore, with the modified polycarbonate A (R=CH of highly blood coagulation resistant3, n=0) and there is excellent anticoagulant effect.
Although the anticoagulant effect of subject polymer is by its random copolymer A (R=CH3, n=0) measurement, but subject polymer
Anticoagulant effect should be not excluded for random copolymer, alternate copolymer, block copolymer and the graft copolymerization species of its A, B and C
Type.
Claims (3)
1. a kind of modified polycarbonate with highly blood coagulation resistant is linear carbonate polymer, side chain packet comprising main chain
Containing can functionalization double bond and hydrophilic Phosphorylcholine group, there is following structure, including copolymer A, B and C:
Its preparation process are as follows: be first copolymerized by trimethylene carbonate (TMC) and trimethylene derivative, then by two mercaptan and
The click chemistry of double bond reacts grafting 2- methylacryoyloxyethyl Phosphorylcholine (MPC) on copolymer side chain and obtains target production
Object has the modified polycarbonate of highly blood coagulation resistant.
2. the modified polycarbonate according to claim 1 with highly blood coagulation resistant, which is characterized in that the trimethylene
Derivative includes: 5- methyl -5- allyloxy carbonyl -1,3- dioxanes -2- ketone, 5- allyloxy carbonyl -1,3- dioxanes -2-
Ketone or 5- acryloyloxymethyl -1,3- dioxanes -2- ketone or 5- methacryloxymethyl -1,3- dioxanes -2- ketone or 5-
Acryloyl-oxy -1,3- dioxanes -2- ketone or 5- methacryloxypropyl -1,3- dioxanes -2- ketone.
3. the modified polycarbonate according to claim 1 or 2 with highly blood coagulation resistant, which is characterized in that two sulphur
Alcohol includes: 1,2- dithioglycol, 1,3- dimercaptopropane and 1,4- succinimide mercaptans.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201910161614.0A CN109912790A (en) | 2019-03-04 | 2019-03-04 | A kind of modified polycarbonate with highly blood coagulation resistant |
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| CN201910161614.0A CN109912790A (en) | 2019-03-04 | 2019-03-04 | A kind of modified polycarbonate with highly blood coagulation resistant |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110452214A (en) * | 2019-07-10 | 2019-11-15 | 天津大学 | A kind of cyclic carbonate monomer and its preparation method and application causing ATRP polymerization |
| CN111420129A (en) * | 2020-05-08 | 2020-07-17 | 江南大学 | Preparation method of degradable polycarbonate coating for reducing corrosion rate of medical magnesium-based material |
| CN111437442A (en) * | 2020-05-08 | 2020-07-24 | 江南大学 | Preparation method of degradable electrophoretic coating for magnesium-based medical implant surface |
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| EP2028208A1 (en) * | 2007-08-15 | 2009-02-25 | Tyco Healthcare Group LP | Phospholipid copolymers |
| US20090110713A1 (en) * | 2007-10-31 | 2009-04-30 | Florencia Lim | Biodegradable polymeric materials providing controlled release of hydrophobic drugs from implantable devices |
| CN102712616A (en) * | 2009-07-23 | 2012-10-03 | Ssens有限责任公司 | A method of making a polymer preferably an (alkyl) acryloyl polycarbonate, the polymer and (alkyl)acryloyl polycarbonate obtained, and a biodevice comprising same |
| CN103492489A (en) * | 2010-04-15 | 2014-01-01 | 欧利加希斯公司 | High molecular weight zwitterion-containing polymers |
| CN104448153A (en) * | 2013-09-17 | 2015-03-25 | 同济大学 | Phosphorylcholine-containing high-strength polyurethane hydrogel and preparation method thereof |
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2019
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2028208A1 (en) * | 2007-08-15 | 2009-02-25 | Tyco Healthcare Group LP | Phospholipid copolymers |
| US20090110713A1 (en) * | 2007-10-31 | 2009-04-30 | Florencia Lim | Biodegradable polymeric materials providing controlled release of hydrophobic drugs from implantable devices |
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| CN103492489A (en) * | 2010-04-15 | 2014-01-01 | 欧利加希斯公司 | High molecular weight zwitterion-containing polymers |
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| TATSURO GODA ET AL.: "Thiolated 2-methacryloyloxyethyl phosphorylcholine for an antifouling biosensor platform", 《CHEM. COMM.》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110452214A (en) * | 2019-07-10 | 2019-11-15 | 天津大学 | A kind of cyclic carbonate monomer and its preparation method and application causing ATRP polymerization |
| CN110452214B (en) * | 2019-07-10 | 2022-06-28 | 天津大学 | Cyclic carbonate monomer capable of initiating ATRP polymerization, and preparation method and application thereof |
| CN111420129A (en) * | 2020-05-08 | 2020-07-17 | 江南大学 | Preparation method of degradable polycarbonate coating for reducing corrosion rate of medical magnesium-based material |
| CN111437442A (en) * | 2020-05-08 | 2020-07-24 | 江南大学 | Preparation method of degradable electrophoretic coating for magnesium-based medical implant surface |
| CN111437442B (en) * | 2020-05-08 | 2021-09-21 | 江南大学 | Preparation method of degradable electrophoretic coating for magnesium-based medical implant surface |
| CN111420129B (en) * | 2020-05-08 | 2021-11-02 | 江南大学 | Preparation method of degradable polycarbonate coating for reducing corrosion rate of medical magnesium-based material |
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