JP2022508631A - 形状記憶高分子を含む鼻涙管挿入用部材 - Google Patents
形状記憶高分子を含む鼻涙管挿入用部材 Download PDFInfo
- Publication number
- JP2022508631A JP2022508631A JP2021544080A JP2021544080A JP2022508631A JP 2022508631 A JP2022508631 A JP 2022508631A JP 2021544080 A JP2021544080 A JP 2021544080A JP 2021544080 A JP2021544080 A JP 2021544080A JP 2022508631 A JP2022508631 A JP 2022508631A
- Authority
- JP
- Japan
- Prior art keywords
- nasolacrimal duct
- shape memory
- memory polymer
- insertion member
- polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 210000004083 nasolacrimal duct Anatomy 0.000 title claims abstract description 174
- 229920000431 shape-memory polymer Polymers 0.000 title claims abstract description 121
- 238000003780 insertion Methods 0.000 title claims description 89
- 230000037431 insertion Effects 0.000 title claims description 89
- 238000002844 melting Methods 0.000 claims abstract description 51
- 230000008018 melting Effects 0.000 claims abstract description 50
- 238000004132 cross linking Methods 0.000 claims abstract description 33
- 239000000126 substance Substances 0.000 claims description 46
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 abstract description 7
- 208000000617 lacrimal duct obstruction Diseases 0.000 abstract description 7
- 208000031481 Pathologic Constriction Diseases 0.000 abstract description 5
- 230000036262 stenosis Effects 0.000 abstract description 5
- 208000037804 stenosis Diseases 0.000 abstract description 5
- 229920002189 poly(glycerol 1-O-monomethacrylate) polymer Polymers 0.000 description 62
- 229920000642 polymer Polymers 0.000 description 55
- 229920001610 polycaprolactone Polymers 0.000 description 43
- 239000004632 polycaprolactone Substances 0.000 description 37
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical group O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 29
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- 230000000052 comparative effect Effects 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000011521 glass Substances 0.000 description 19
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 19
- 238000006116 polymerization reaction Methods 0.000 description 18
- 238000011084 recovery Methods 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 239000000178 monomer Substances 0.000 description 15
- 230000008569 process Effects 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000000113 differential scanning calorimetry Methods 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 238000005227 gel permeation chromatography Methods 0.000 description 8
- 238000002054 transplantation Methods 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- 238000010586 diagram Methods 0.000 description 7
- 230000012010 growth Effects 0.000 description 7
- 230000001939 inductive effect Effects 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 6
- 230000007246 mechanism Effects 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 210000001519 tissue Anatomy 0.000 description 6
- 241000909851 Epiphora Species 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 208000016747 lacrimal apparatus disease Diseases 0.000 description 5
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 206010010356 Congenital anomaly Diseases 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 208000010217 blepharitis Diseases 0.000 description 4
- 230000004054 inflammatory process Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002861 polymer material Substances 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- FVKFHMNJTHKMRX-UHFFFAOYSA-N 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine Chemical compound C1CCN2CCCNC2=N1 FVKFHMNJTHKMRX-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 229920000954 Polyglycolide Polymers 0.000 description 3
- 241000083513 Punctum Species 0.000 description 3
- 230000036760 body temperature Effects 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- UURSXESKOOOTOV-UHFFFAOYSA-N dec-5-ene Chemical compound CCCCC=CCCCC UURSXESKOOOTOV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 210000002919 epithelial cell Anatomy 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000004660 morphological change Effects 0.000 description 3
- 230000035479 physiological effects, processes and functions Effects 0.000 description 3
- 229920000747 poly(lactic acid) Polymers 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 229920001059 synthetic polymer Polymers 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 230000035899 viability Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010010741 Conjunctivitis Diseases 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 230000005856 abnormality Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 230000007815 allergy Effects 0.000 description 2
- 239000012620 biological material Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 210000004204 blood vessel Anatomy 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 230000010261 cell growth Effects 0.000 description 2
- 208000037976 chronic inflammation Diseases 0.000 description 2
- 230000006020 chronic inflammation Effects 0.000 description 2
- 208000021921 corneal disease Diseases 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 230000003013 cytotoxicity Effects 0.000 description 2
- 231100000135 cytotoxicity Toxicity 0.000 description 2
- 238000004925 denaturation Methods 0.000 description 2
- 230000036425 denaturation Effects 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 201000004356 excessive tearing Diseases 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- JUYQFRXNMVWASF-UHFFFAOYSA-M lithium;phenyl-(2,4,6-trimethylbenzoyl)phosphinate Chemical compound [Li+].CC1=CC(C)=CC(C)=C1C(=O)P([O-])(=O)C1=CC=CC=C1 JUYQFRXNMVWASF-UHFFFAOYSA-M 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 210000004379 membrane Anatomy 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 description 2
- 239000004626 polylactic acid Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 208000005494 xerophthalmia Diseases 0.000 description 2
- -1 zinc succinate (3-mercaptopropionate) Chemical compound 0.000 description 2
- FZTLLUYFWAOGGB-UHFFFAOYSA-N 1,4-dioxane dioxane Chemical compound C1COCCO1.C1COCCO1 FZTLLUYFWAOGGB-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- XBBVURRQGJPTHH-UHFFFAOYSA-N 2-hydroxyacetic acid;2-hydroxypropanoic acid Chemical compound OCC(O)=O.CC(O)C(O)=O XBBVURRQGJPTHH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 206010011469 Crying Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010023644 Lacrimation increased Diseases 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- HTRXGEPDTFSKLI-UHFFFAOYSA-N butanoic acid;ethyl acetate Chemical compound CCCC(O)=O.CCOC(C)=O HTRXGEPDTFSKLI-UHFFFAOYSA-N 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000021164 cell adhesion Effects 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 238000010382 chemical cross-linking Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000000744 eyelid Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 210000004561 lacrimal apparatus Anatomy 0.000 description 1
- 230000004317 lacrimation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000002050 maxilla Anatomy 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- 230000007087 memory ability Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 238000012148 non-surgical treatment Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004633 polyglycolic acid Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002966 stenotic effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- 238000005406 washing Methods 0.000 description 1
- AGFGXVAAIXIOFZ-UHFFFAOYSA-L zinc;butanedioate Chemical compound [Zn+2].[O-]C(=O)CCC([O-])=O AGFGXVAAIXIOFZ-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/04—Macromolecular materials
- A61L29/041—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F9/00—Methods or devices for treatment of the eyes; Devices for putting-in contact lenses; Devices to correct squinting; Apparatus to guide the blind; Protective devices for the eyes, carried on the body or in the hand
- A61F9/007—Methods or devices for eye surgery
- A61F9/00772—Apparatus for restoration of tear ducts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/04—Macromolecular materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M27/00—Drainage appliance for wounds or the like, i.e. wound drains, implanted drains
- A61M27/002—Implant devices for drainage of body fluids from one part of the body to another
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/664—Polyesters containing oxygen in the form of ether groups derived from hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/062—Copolymers with monomers not covered by C08L33/06
- C08L33/068—Copolymers with monomers not covered by C08L33/06 containing glycidyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F2210/00—Particular material properties of prostheses classified in groups A61F2/00 - A61F2/26 or A61F2/82 or A61F9/00 or A61F11/00 or subgroups thereof
- A61F2210/0004—Particular material properties of prostheses classified in groups A61F2/00 - A61F2/26 or A61F2/82 or A61F9/00 or A61F11/00 or subgroups thereof bioabsorbable
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F2210/00—Particular material properties of prostheses classified in groups A61F2/00 - A61F2/26 or A61F2/82 or A61F9/00 or A61F11/00 or subgroups thereof
- A61F2210/0014—Particular material properties of prostheses classified in groups A61F2/00 - A61F2/26 or A61F2/82 or A61F9/00 or A61F11/00 or subgroups thereof using shape memory or superelastic materials, e.g. nitinol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/16—Materials with shape-memory or superelastic properties
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2430/00—Materials or treatment for tissue regeneration
- A61L2430/22—Materials or treatment for tissue regeneration for reconstruction of hollow organs, e.g. bladder, esophagus, urether, uterus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2280/00—Compositions for creating shape memory
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Ophthalmology & Optometry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Dermatology (AREA)
- Transplantation (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Vascular Medicine (AREA)
- Otolaryngology (AREA)
- Anesthesiology (AREA)
- Hematology (AREA)
- Materials For Medical Uses (AREA)
- Polyesters Or Polycarbonates (AREA)
- Prostheses (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Abstract
Description
本発明の実施例において、
下記化学式1で表される形状記憶高分子を含む鼻涙管挿入用部材を提供する:
R1、R2及びR3は、それぞれ独立に水素(H)又は炭素数1~6のアルキル基であり、
m及びnは、それぞれ独立に1~20の整数であり、
A、B1及びB2は、それぞれ独立に酸素(O)又は硫黄(S)であり、
x及びyは、反復単位のモル%を表し、
x+yは100であり、xは80~95である。
下記化学式1で表される形状記憶高分子を含む鼻涙管挿入用部材を提供する:
R1、R2及びR3は、それぞれ独立に水素(H)又は炭素数1~6のアルキル基であり、
m及びnは、それぞれ独立に1~20の整数であり、
A、B1及びB2は、それぞれ独立に酸素(O)又は硫黄(S)であり、
x及びyは、反復単位のモル%を表し、
x+yは100であり、xは80~95である。
前記化学式1において、
R1、R2及びR3は、それぞれ独立に水素(H)又はメチル基(CH3-)であり、
m及びnは、それぞれ独立に3~12の整数であり、
A、B1及びB2はいずれも酸素(O)であり、
x及びyは、反復単位のモル%を表し、
x+y=100であり、xは88~94である。
前記化学式1において、
R1、R2及びR3は、それぞれ独立に水素(H)であり、
m及びnは、それぞれ独立に5~6の整数であり、
A、B1及びB2は、それぞれ独立に酸素(O)であり、
x及びyは、反復単位のモル%を表し、
x+y=100であり、xは88~94である。
m及びnは、それぞれ独立に1~20の整数であり、
x及びyは、反復単位のモル%を表し、
x+yは100であり、xは80~95である。
R1、R2及びR3は、それぞれ独立に水素(H)又は炭素(C)数1~6のアルキル基(CnH2n+1-)であり、
m及びnは、それぞれ独立に1~20の整数であり、
A、B1及びB2は、それぞれ独立に酸素(O)又は硫黄(S)である。
上述の形状記憶高分子を含む鼻涙管挿入用部材を提供する。以下、図2~図4を参照して、本発明の一実施例に係る鼻涙管挿入用部材を詳細に説明する。
1.試料及び機構
ε-カプロラクトン(CL;caprolactone)、ハイドロキノン(HQ;Hydroquinone)、1,5,7-トリアザビシクロ[4.4.0]-5-デセン(TBD;1,5,7-triazabicyclo[4.4.0]dec-5-ene)、グリシジルメタクリレート(GMA;Glycidyl methacrylate)、アセトニトリル(Acetonitrile)、クロロホルム(Chloroform)、ジクロロメタン(Dichloromethane)、ジエチルエーテル(Diethyl ether)、2,2-ジメトキシ-2-フェニルアセトフェノン(2,2-Dimethoxy-2-phenylacetophenone)及び1,6-ヘキサンジオール(HD;1,6-Hexanediol)は、Sigma-Aldrich社から購入した。
1-1. 94%PCL-co-6%PGMAの合成
1-1-1. 94%PCL-co-6%PGMAの合成
94%PCL-co-6%PGMAを合成するために、[CL]0/[GMA]0/[HD]0/[TBD]0/[HQ]0=90/10/1/1/0.5の反応物投入比で次のように合成した(表1参照)。
反応後に反応物7.5gをクロロホルム10mlに溶解させた以外は、以降の重合方法は実施例1-1-1と同一である。
反応後に反応物10gをクロロホルム10mlに溶解させた以外は、以降の重合方法は実施例1-1-1と同一である。
92%PCL-co-8%PGMAを合成するために、[CL]0/[GMA]0/[HD]0/[TBD]0/[HQ]0=86/14/1.4/1/0.5の反応物投入比で次のように合成した(表2参照)。
90%PCL-co-10%PGMAを合成するために、[CL]0/[GMA]0/[HD]0/[TBD]0/[HQ]0=82/18/1.8/1/0.5の反応物投入比で次のように合成した(表3参照)。
88%PCL-co-12%PGMAを合成するために、[CL]0/[GMA]0/[HD]0/[TBD]0/[HQ]0=78/22/2.2/1/0.5の反応物投入比で次のように合成した(表4参照)。
[0CL]0/[GMA]0/[HD]0/[TBD]0/[HQ]0を次のような反応物投入比にして高分子を合成した(実施例2-1~2-4)。
実施例1-1-1で製造した高分子を用いて鼻涙管挿入用部材を製造した。
[0CL]0/[HD]0/[TBD]0=100/0.5/1の反応物投入比で次のように重合した。
[0CL]0/[HD]0/[TBD]0=100/0.5/0.5の反応物投入比で次のように重合した。
1-1. UV架橋を用いた形状記憶高分子材料の製造
図9は、実施例1-1-1と比較例1で合成した高分子にUV(Ultraviolet ray)処理した後に現れる現象を比較した図である。
図10及び表8は、実施例1と比較例1のDSC分析を示すグラフ及び表である。
図11及び表9は、実施例1-1-1と比較例1の高分子にUV処理した後のDSC分析を示すグラフ及び表である。
実験例2では、実施例2-1~2-4と比較例2で合成した高分子の融点を測定し、UV処理した形状記憶高分子のDSC分析とGPC分析を行った。
前記実施例1で合成した形状記憶高分子の形状記憶特性を図13に示した((a)初期状態、(b)変形された状態、(c)復元された状態)。
変形回復率(Rr)={(Ie-Ir)/(Ie-Io)}×100
Io:初期サンプルの長さ
Ie:変形されたサンプルの長さ
Ir:回復後のサンプルの長さ
したがって、実施例4でUV処理した90%PCL-co-10%PGMA形状記憶高分子材料の変形回復率は90%以上であって、復原力に優れることが確認でき、融点が低い点から生体材料に適合したものと判断される。
4-1.形状記憶高分子の圧縮強度測定
実施例1-1で合成した94%PCL-co-6%PGMA高分子の強度、構造度、融点を測定した。
ASTM D412に記載の試験方法によって試験して測定した。
合成された高分子の構成成分(PCLとPGMAの水素原子個数比によるPCLとPGMAの反復単位比)を1H NMR(nuclear magnetic resonance)を用いて測定した。
高分子の融点を分析するために時差走査熱量測定法(DSC,Differential scanning calorimetry)で測定した。
比較例1(PCL)の高分子と形状記憶高分子(96%PCL-co-4%PGMA高分子、94%PCL-co-6%PGMA高分子、92%PCL-co-8%PGMA高分子)の表面上に蒸留水を一滴(10μg)落とし、接触角を分析するために撮影した後、その結果を図14に示した。
実施例3で製造した鼻涙管挿入用部材(94%PCL-co-6%PGMA)の細胞毒性を測定するために、L929細胞(mouse cell line)を対照群(細胞培養器)と前記鼻涙管挿入用部材の高分子フィルム上で培養した。
図15を参照すると、本発明の高分子は、食品医薬品安全処の許可を通過できる80%以上の細胞生存性を示した。
実施例3で製造した鼻涙管挿入用部材を用いて細胞の付着率と細胞の生長率を測定した。
実験例7.鼻涙管挿入用部材の復元
図17は、実施例3で製造した鼻涙管挿入用部材が変形温度条件下で初期の状態に復元される過程を示す図である((a)初期状態、(b)変形された状態、(c)回復した状態(40℃))。すなわち、図17は、鼻涙管挿入用部材の実現可能性を示す図である。
図17を参照すると、15mm長の太いチューブ挿入物が、鼻涙管への挿入前の臨時状態(temporary shape)では29mm長に伸張され、その直径が細くなることが確認できる。そして、鼻涙管内に挿入後、温度を40℃に上げた場合、再び長さ15mmに減り、直径が太くなることが確認できた。すなわち、形状記憶プログラミングの可能性が確認できた。
結論的に、実験例7から、形状記憶高分子材料の優れた変形回復率及び復原力が確認でき、また、融点が低い点から、生体材料に適合すると判断される。
実施例3で製造した鼻涙管挿入用部材とシリコンで製造した鼻涙管挿入用部材を正常ウサギの鼻涙管に挿入して2週後に組織反応を観察した。
2 涙嚢
3 鼻涙管
10 鼻涙管挿入用部材
Claims (8)
- 前記化学式1において、
R1、R2及びR3は、それぞれ独立に水素(H)又はメチル基であり、
m及びnは、それぞれ独立に3~12の整数であり、
A、B1及びB2は、それぞれ独立に酸素(O)又は硫黄(S)であり、
x及びyは反復単位のモル%を表し、
x+y=100であり、xは88~94である、請求項1に記載の鼻涙管挿入用部材。 - 形状記憶高分子は、平均30~48℃の融点を有する、請求項1に記載の鼻涙管挿入用部材。
- 形状記憶高分子は、架橋後に平均で28~42℃の融点を有する、請求項1に記載の鼻涙管挿入用部材。
- 鼻涙管挿入用部材は、
鼻涙管内部に挿入され、チューブ(tube)形態であることを特徴とする、請求項1に記載の鼻涙管挿入用部材。 - 鼻涙管挿入用部材は、
平均で28~42℃以上の温度で鼻涙管内部で形態が変形されることを特徴とする、請求項6に記載の鼻涙管挿入用部材。 - 鼻涙管挿入用部材は、平均で28~42℃の以上の温度において平均で0.4~1.2mmの直径を保持することを特徴とする、請求項7に記載の鼻涙管挿入用部材。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020180117796A KR102521685B1 (ko) | 2018-10-02 | 2018-10-02 | 형상기억 고분자를 포함하는 비루관 튜브 |
KR10-2018-0117796 | 2018-10-02 | ||
PCT/KR2019/012824 WO2020071732A1 (ko) | 2018-10-02 | 2019-10-01 | 형상기억 고분자를 포함하는 비루관 삽입용 부재 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2022508631A true JP2022508631A (ja) | 2022-01-19 |
JP7283807B2 JP7283807B2 (ja) | 2023-05-30 |
Family
ID=70054759
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2021544080A Active JP7283807B2 (ja) | 2018-10-02 | 2019-10-01 | 形状記憶高分子を含む鼻涙管挿入用部材 |
Country Status (5)
Country | Link |
---|---|
US (1) | US20210369920A1 (ja) |
EP (1) | EP3875125A4 (ja) |
JP (1) | JP7283807B2 (ja) |
KR (1) | KR102521685B1 (ja) |
WO (1) | WO2020071732A1 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2024500501A (ja) * | 2020-12-23 | 2024-01-09 | ティーエムディー ラブ カンパニー,リミテッド | 眼圧調節のための新規な房水流出装置 |
KR102614952B1 (ko) * | 2022-11-30 | 2023-12-19 | 주식회사 티엠디랩 | 몰딩 특성을 가지는 형상 기억 고분자 기반 치과용 멤브레인 및 이의 제조방법 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2018522992A (ja) * | 2015-04-15 | 2018-08-16 | ヴァンダービルト ユニバーシティーVanderbilt University | 形状記憶型外ステントの開発及び血管適用 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4380239A (en) | 1979-12-20 | 1983-04-19 | The Hospital For Sick Children | Intubation of lacrimal ducts |
KR100408458B1 (ko) * | 2000-12-27 | 2003-12-06 | 한국과학기술연구원 | 생분해성 글리콜라이드/ε-카프로락톤 공중합체로부터 제조된 조직공학용 다공성 지지체 |
KR101606112B1 (ko) | 2015-03-10 | 2016-03-29 | 가톨릭대학교 산학협력단 | mPEG-b-RSPCL-b-mPEG 블록공중합체 및 상기 블록공중합체를 이용한 나노약물전달용 조성물 |
WO2016205107A1 (en) * | 2015-06-16 | 2016-12-22 | The Regents Of The University Of Colorado, A Body Corporate | Nasolacrimal implants and related methods for tear stimulation |
KR101906472B1 (ko) * | 2017-04-04 | 2018-10-10 | 연세대학교 산학협력단 | 광가교가 가능한 형상기억고분자 및 이의 제조방법 |
KR101974043B1 (ko) | 2017-04-20 | 2019-04-30 | 이재광 | 연속 컷팅 장치 |
KR101999233B1 (ko) * | 2017-12-19 | 2019-09-27 | 부산대학교 산학협력단 | 코눈물관 폐쇄에서 실리콘관 삽입술의 생분해성고분자 매듭을 포함하는 실리콘관 |
JP7283808B2 (ja) | 2018-10-02 | 2023-05-30 | ティーエムディー ラブ カンパニー,リミテッド | 形状記憶高分子を含む血管吻合用部材 |
-
2018
- 2018-10-02 KR KR1020180117796A patent/KR102521685B1/ko active IP Right Grant
-
2019
- 2019-10-01 JP JP2021544080A patent/JP7283807B2/ja active Active
- 2019-10-01 US US17/281,666 patent/US20210369920A1/en active Pending
- 2019-10-01 EP EP19869808.6A patent/EP3875125A4/en active Pending
- 2019-10-01 WO PCT/KR2019/012824 patent/WO2020071732A1/ko unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2018522992A (ja) * | 2015-04-15 | 2018-08-16 | ヴァンダービルト ユニバーシティーVanderbilt University | 形状記憶型外ステントの開発及び血管適用 |
Non-Patent Citations (2)
Title |
---|
IRANIAN POLYMER JOURNAL, vol. Vol.20(4), JPN6022017052, 2011, pages 329 - 340, ISSN: 0005045567 * |
POLYMER JOURNAL, vol. 46, JPN6022017051, 2014, pages 598 - 608, ISSN: 0005045568 * |
Also Published As
Publication number | Publication date |
---|---|
JP7283807B2 (ja) | 2023-05-30 |
EP3875125A1 (en) | 2021-09-08 |
KR20200038102A (ko) | 2020-04-10 |
US20210369920A1 (en) | 2021-12-02 |
KR102521685B1 (ko) | 2023-04-14 |
EP3875125A4 (en) | 2022-07-06 |
WO2020071732A1 (ko) | 2020-04-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US11628235B2 (en) | Photo-cross-linkable shape-memory polymer and preparation method therefor | |
CA2527976C (en) | Stents | |
CA2527975C (en) | Biodegradable stents comprising a shape memory polymeric material | |
CN101443055B (zh) | 管状组织支持器的移除方法 | |
Chien et al. | Preparation, characterization, and mechanism for biodegradable and biocompatible polyurethane shape memory elastomers | |
JP7283808B2 (ja) | 形状記憶高分子を含む血管吻合用部材 | |
CN112386747B (zh) | 一种具备记忆形状功能的输尿管支架管及其制备方法与用途 | |
JP7283807B2 (ja) | 形状記憶高分子を含む鼻涙管挿入用部材 | |
JP2023532026A (ja) | 温度ベース形状記憶高分子 | |
KR102208921B1 (ko) | 형상기억 고분자, 이의 제조방법 및 용도 | |
Antony et al. | Tailored poly (ethylene) glycol dimethacrylate based shape memory polymer for orthopedic applications | |
Qu et al. | 4D printing of shape memory inferior vena cava filters based on copolymer of poly (glycerol sebacate) acrylate-co-hydroxyethyl methacrylate (PGSA-HEMA) | |
KR102208920B1 (ko) | 형상기억 고분자, 이의 제조방법 및 용도 | |
JP4798662B2 (ja) | ステント | |
JP4881728B2 (ja) | 生分解性ステント | |
KR102547679B1 (ko) | 자가팽창성 및 바이오필름 저감 특성을 가지는 형상기억고분자 및 이의 의료용 소재로서의 용도 | |
KR20230056862A (ko) | 온도 감응성 형상기억 고분자 | |
WO2008019875A1 (en) | Tubular tissue support | |
Ma et al. | Advances in 4D printing of biodegradable photopolymers | |
KR20220118841A (ko) | 형상기억고분자, 이의 제조방법 및 용도 | |
KR20220118843A (ko) | 형상기억고분자, 이의 제조방법 및 용도 | |
LOO | From Plastics to Advanced Polymer Implants: The Essentials of Polymer Chemistry |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20210402 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20220510 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20220809 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20221007 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20221108 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20230308 |
|
C60 | Trial request (containing other claim documents, opposition documents) |
Free format text: JAPANESE INTERMEDIATE CODE: C60 Effective date: 20230308 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20230310 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20230330 |
|
C21 | Notice of transfer of a case for reconsideration by examiners before appeal proceedings |
Free format text: JAPANESE INTERMEDIATE CODE: C21 Effective date: 20230404 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20230425 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20230511 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7283807 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |