JP2005539098A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2005539098A5 JP2005539098A5 JP2003575849A JP2003575849A JP2005539098A5 JP 2005539098 A5 JP2005539098 A5 JP 2005539098A5 JP 2003575849 A JP2003575849 A JP 2003575849A JP 2003575849 A JP2003575849 A JP 2003575849A JP 2005539098 A5 JP2005539098 A5 JP 2005539098A5
- Authority
- JP
- Japan
- Prior art keywords
- hema
- poly
- group
- composition
- molecular weight
- 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
- 239000000243 solution Substances 0.000 claims description 143
- 238000000034 method Methods 0.000 claims description 129
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 claims description 100
- 239000000203 mixture Substances 0.000 claims description 95
- 239000000178 monomer Substances 0.000 claims description 84
- 229920000642 polymer Polymers 0.000 claims description 70
- 239000002904 solvent Substances 0.000 claims description 64
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 50
- 239000003085 diluting agent Substances 0.000 claims description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 49
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 47
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 41
- 239000000017 hydrogel Substances 0.000 claims description 41
- 102100026735 Coagulation factor VIII Human genes 0.000 claims description 35
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 claims description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- 239000003999 initiator Substances 0.000 claims description 31
- 125000000524 functional group Chemical group 0.000 claims description 26
- 238000000926 separation method Methods 0.000 claims description 24
- 229920001223 polyethylene glycol Polymers 0.000 claims description 23
- 238000006116 polymerization reaction Methods 0.000 claims description 22
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 19
- 238000004132 cross linking Methods 0.000 claims description 17
- 229920001577 copolymer Polymers 0.000 claims description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 15
- 238000005194 fractionation Methods 0.000 claims description 14
- 238000010526 radical polymerization reaction Methods 0.000 claims description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 13
- 238000000465 moulding Methods 0.000 claims description 13
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 12
- 239000002202 Polyethylene glycol Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 238000001704 evaporation Methods 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 150000001298 alcohols Chemical class 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- -1 ester alcohols Chemical class 0.000 claims description 11
- 230000008020 evaporation Effects 0.000 claims description 11
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000000376 reactant Substances 0.000 claims description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
- 238000005406 washing Methods 0.000 claims description 11
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000008367 deionised water Substances 0.000 claims description 9
- 229910021641 deionized water Inorganic materials 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- 150000008065 acid anhydrides Chemical class 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 230000002209 hydrophobic effect Effects 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 7
- 230000008901 benefit Effects 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 7
- 230000002829 reductive effect Effects 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 238000009826 distribution Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 6
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical group CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 6
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 claims description 5
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 5
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 229940116333 ethyl lactate Drugs 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 claims description 5
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 claims description 5
- 229940057867 methyl lactate Drugs 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 229920001296 polysiloxane Polymers 0.000 claims description 5
- KIWATKANDHUUOB-UHFFFAOYSA-N propan-2-yl 2-hydroxypropanoate Chemical compound CC(C)OC(=O)C(C)O KIWATKANDHUUOB-UHFFFAOYSA-N 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- IQAGXMNEUYBTLG-UHFFFAOYSA-N 5-hydroxy-2-methylpent-2-enamide Chemical compound NC(=O)C(C)=CCCO IQAGXMNEUYBTLG-UHFFFAOYSA-N 0.000 claims description 4
- LFOXEOLGJPJZAA-UHFFFAOYSA-N [(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphoryl]-(2,6-dimethoxyphenyl)methanone Chemical group COC1=CC=CC(OC)=C1C(=O)P(=O)(CC(C)CC(C)(C)C)C(=O)C1=C(OC)C=CC=C1OC LFOXEOLGJPJZAA-UHFFFAOYSA-N 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 claims description 4
- 230000008602 contraction Effects 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- 239000007863 gel particle Substances 0.000 claims description 4
- 150000002334 glycols Chemical class 0.000 claims description 4
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 claims description 4
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 claims description 3
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 claims description 3
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 claims description 3
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical group CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 claims description 3
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 3
- DPNXHTDWGGVXID-UHFFFAOYSA-N 2-isocyanatoethyl prop-2-enoate Chemical compound C=CC(=O)OCCN=C=O DPNXHTDWGGVXID-UHFFFAOYSA-N 0.000 claims description 3
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
- 102100026827 Protein associated with UVRAG as autophagy enhancer Human genes 0.000 claims description 3
- 101710102978 Protein associated with UVRAG as autophagy enhancer Proteins 0.000 claims description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 3
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 claims description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical compound NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 0.000 claims description 3
- JLBXCKSMESLGTJ-UHFFFAOYSA-N 1-ethoxypropan-1-ol Chemical compound CCOC(O)CC JLBXCKSMESLGTJ-UHFFFAOYSA-N 0.000 claims description 2
- 229940044613 1-propanol Drugs 0.000 claims description 2
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 claims description 2
- 241000975394 Evechinus chloroticus Species 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- 229960004756 ethanol Drugs 0.000 claims description 2
- 239000001023 inorganic pigment Substances 0.000 claims description 2
- 229960004592 isopropanol Drugs 0.000 claims description 2
- GORGQKRVQGXVEB-UHFFFAOYSA-N n-ethenyl-n-ethylacetamide Chemical compound CCN(C=C)C(C)=O GORGQKRVQGXVEB-UHFFFAOYSA-N 0.000 claims description 2
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims description 2
- 239000012860 organic pigment Substances 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 150000004040 pyrrolidinones Chemical class 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 239000000985 reactive dye Substances 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims 4
- 229920000570 polyether Polymers 0.000 claims 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 2
- 125000005594 diketone group Chemical group 0.000 claims 2
- 238000010790 dilution Methods 0.000 claims 2
- 239000012895 dilution Substances 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 102000004169 proteins and genes Human genes 0.000 claims 2
- 108090000623 proteins and genes Proteins 0.000 claims 2
- 238000007493 shaping process Methods 0.000 claims 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims 1
- VVXNMKJDQVBOLT-UHFFFAOYSA-N 3-methoxybutanal Chemical compound COC(C)CC=O VVXNMKJDQVBOLT-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 239000004971 Cross linker Substances 0.000 claims 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- 230000003796 beauty Effects 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 230000000977 initiatory effect Effects 0.000 claims 1
- 238000010550 living polymerization reaction Methods 0.000 claims 1
- AHIHJODVQGBOND-UHFFFAOYSA-M propan-2-yl carbonate Chemical compound CC(C)OC([O-])=O AHIHJODVQGBOND-UHFFFAOYSA-M 0.000 claims 1
- 239000012071 phase Substances 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 29
- 239000000463 material Substances 0.000 description 24
- 238000007306 functionalization reaction Methods 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 238000001556 precipitation Methods 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 230000000875 corresponding effect Effects 0.000 description 7
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 230000005855 radiation Effects 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 5
- 102100040409 Ameloblastin Human genes 0.000 description 5
- 101000891247 Homo sapiens Ameloblastin Proteins 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 5
- WUGOQZFPNUYUOO-UHFFFAOYSA-N 2-trimethylsilyloxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCO[Si](C)(C)C WUGOQZFPNUYUOO-UHFFFAOYSA-N 0.000 description 4
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000012986 chain transfer agent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001542 size-exclusion chromatography Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 0 CC(C(OCC(*)COCCCN(OC)ON)=O)=C Chemical compound CC(C(OCC(*)COCCCN(OC)ON)=O)=C 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- UUQLCJCZFWUWHH-UHFFFAOYSA-N lithium;1-phenylhexylbenzene Chemical compound [Li+].C=1C=CC=CC=1[C-](CCCCC)C1=CC=CC=C1 UUQLCJCZFWUWHH-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 description 2
- 238000001374 small-angle light scattering Methods 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 1
- BSPCSKHALVHRSR-UHFFFAOYSA-N 2-chlorobutane Chemical compound CCC(C)Cl BSPCSKHALVHRSR-UHFFFAOYSA-N 0.000 description 1
- RCEJCSULJQNRQQ-UHFFFAOYSA-N 2-methylbutanenitrile Chemical compound CCC(C)C#N RCEJCSULJQNRQQ-UHFFFAOYSA-N 0.000 description 1
- NWBTXZPDTSKZJU-UHFFFAOYSA-N 3-[dimethyl(trimethylsilyloxy)silyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](C)(C)O[Si](C)(C)C NWBTXZPDTSKZJU-UHFFFAOYSA-N 0.000 description 1
- HBOYQHJSMXAOKY-UHFFFAOYSA-N 3-[methyl-bis(trimethylsilyloxy)silyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C HBOYQHJSMXAOKY-UHFFFAOYSA-N 0.000 description 1
- BESKSSIEODQWBP-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C BESKSSIEODQWBP-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- HTIRHQRTDBPHNZ-UHFFFAOYSA-N Dibutyl sulfide Chemical compound CCCCSCCCC HTIRHQRTDBPHNZ-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 101000610640 Homo sapiens U4/U6 small nuclear ribonucleoprotein Prp3 Proteins 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 241000287463 Phalacrocorax Species 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 241001417524 Pomacanthidae Species 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 101001110823 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-A Proteins 0.000 description 1
- 101000712176 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-B Proteins 0.000 description 1
- 229910018557 Si O Inorganic materials 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 102100040374 U4/U6 small nuclear ribonucleoprotein Prp3 Human genes 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- PKDAKIZIHVXQTQ-UHFFFAOYSA-N [2-hydroxy-3-[3-tris(trimethylsilyloxy)silylpropoxy]propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)COCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C PKDAKIZIHVXQTQ-UHFFFAOYSA-N 0.000 description 1
- UHPPAPGGMSFXNF-UHFFFAOYSA-N [2-hydroxy-3-[[propyl-bis(trimethylsilyloxy)silyl]methoxy]propyl] 2-methylprop-2-enoate Chemical compound CCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)COCC(O)COC(=O)C(C)=C UHPPAPGGMSFXNF-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- ZNAAXKXXDQLJIX-UHFFFAOYSA-N bis(2-cyclohexyl-3-hydroxyphenyl)methanone Chemical compound C1CCCCC1C=1C(O)=CC=CC=1C(=O)C1=CC=CC(O)=C1C1CCCCC1 ZNAAXKXXDQLJIX-UHFFFAOYSA-N 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000004590 computer program Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000013036 cure process Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- DTPCFIHYWYONMD-UHFFFAOYSA-N decaethylene glycol Chemical group OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO DTPCFIHYWYONMD-UHFFFAOYSA-N 0.000 description 1
- VTXVGVNLYGSIAR-UHFFFAOYSA-N decane-1-thiol Chemical compound CCCCCCCCCCS VTXVGVNLYGSIAR-UHFFFAOYSA-N 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 125000001303 disiloxanyl group Chemical group [H][Si]([*])([H])O[Si]([H])([H])[H] 0.000 description 1
- GARATWANNPLCAP-UHFFFAOYSA-N dodecane-1-thiol;2-sulfanylethanol Chemical compound OCCS.CCCCCCCCCCCCS GARATWANNPLCAP-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000007765 extrusion coating Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 239000013627 low molecular weight specie Substances 0.000 description 1
- 238000007620 mathematical function Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000013138 pruning Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36363902P | 2002-03-11 | 2002-03-11 | |
| US60/363,639 | 2002-03-11 | ||
| US10/367,253 | 2003-02-14 | ||
| US10/367,253 US6846892B2 (en) | 2002-03-11 | 2003-02-14 | Low polydispersity poly-HEMA compositions |
| PCT/US2003/006835 WO2003077792A2 (en) | 2002-03-11 | 2003-03-06 | Low polydispersity poly-hema compositions |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009159594A Division JP5697317B2 (ja) | 2002-03-11 | 2009-07-06 | 低多分散性ポリｈｅｍａ組成物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005539098A JP2005539098A (ja) | 2005-12-22 |
| JP2005539098A5 true JP2005539098A5 (enExample) | 2009-08-27 |
| JP5220260B2 JP5220260B2 (ja) | 2013-06-26 |
Family
ID=28045323
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003575849A Expired - Fee Related JP5220260B2 (ja) | 2002-03-11 | 2003-03-06 | 低多分散性ポリｈｅｍａ組成物 |
| JP2009159594A Expired - Fee Related JP5697317B2 (ja) | 2002-03-11 | 2009-07-06 | 低多分散性ポリｈｅｍａ組成物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009159594A Expired - Fee Related JP5697317B2 (ja) | 2002-03-11 | 2009-07-06 | 低多分散性ポリｈｅｍａ組成物 |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US6846892B2 (enExample) |
| EP (1) | EP1567567B1 (enExample) |
| JP (2) | JP5220260B2 (enExample) |
| KR (1) | KR100899364B1 (enExample) |
| AR (2) | AR038934A1 (enExample) |
| AU (1) | AU2003224658B2 (enExample) |
| BR (1) | BRPI0317545A2 (enExample) |
| CA (1) | CA2478307C (enExample) |
| DE (1) | DE60334146D1 (enExample) |
| TW (1) | TWI325868B (enExample) |
| WO (1) | WO2003077792A2 (enExample) |
Families Citing this family (98)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030060878A1 (en) * | 2001-08-31 | 2003-03-27 | Shadduck John H. | Intraocular lens system and method for power adjustment |
| US20050258408A1 (en) * | 2001-12-20 | 2005-11-24 | Molock Frank F | Photochromic contact lenses and methods for their production |
| US8048155B2 (en) | 2002-02-02 | 2011-11-01 | Powervision, Inc. | Intraocular implant devices |
| US6846892B2 (en) * | 2002-03-11 | 2005-01-25 | Johnson & Johnson Vision Care, Inc. | Low polydispersity poly-HEMA compositions |
| US20060100408A1 (en) * | 2002-03-11 | 2006-05-11 | Powell P M | Method for forming contact lenses comprising therapeutic agents |
| US8328869B2 (en) | 2002-12-12 | 2012-12-11 | Powervision, Inc. | Accommodating intraocular lenses and methods of use |
| US8361145B2 (en) | 2002-12-12 | 2013-01-29 | Powervision, Inc. | Accommodating intraocular lens system having circumferential haptic support and method |
| US10835373B2 (en) | 2002-12-12 | 2020-11-17 | Alcon Inc. | Accommodating intraocular lenses and methods of use |
| US7217288B2 (en) | 2002-12-12 | 2007-05-15 | Powervision, Inc. | Accommodating intraocular lens having peripherally actuated deflectable surface and method |
| JP2006523130A (ja) | 2003-03-06 | 2006-10-12 | ジョン エイチ． シャダック， | 適合性光学レンズおよび製造方法 |
| EP1623269B2 (en) * | 2003-04-24 | 2022-08-31 | CooperVision International Limited | Hydrogel contact lenses and package systems and production methods for same |
| ATE356515T1 (de) * | 2003-09-03 | 2007-03-15 | Research In Motion Ltd | Verfahren und vorrichtungen zur anzeige eines heimnetzwerknamens |
| WO2006017275A1 (en) | 2004-07-13 | 2006-02-16 | The University Of Tennessee Research Foundation | Adhesive composition for carrying therapeutic agents as delivery vehicle on coatings applied to vascular grafts |
| US20060027939A1 (en) * | 2004-08-03 | 2006-02-09 | Axel Brait | Method for making novel compositions capable of post fabrication modification |
| US9872763B2 (en) | 2004-10-22 | 2018-01-23 | Powervision, Inc. | Accommodating intraocular lenses |
| US9297928B2 (en) | 2004-11-22 | 2016-03-29 | Johnson & Johnson Vision Care, Inc. | Ophthalmic compositions comprising polyether substituted polymers |
| US9381279B2 (en) * | 2005-03-24 | 2016-07-05 | Abbott Cardiovascular Systems Inc. | Implantable devices formed on non-fouling methacrylate or acrylate polymers |
| US7700659B2 (en) * | 2005-03-24 | 2010-04-20 | Advanced Cardiovascular Systems, Inc. | Implantable devices formed of non-fouling methacrylate or acrylate polymers |
| JP5385530B2 (ja) | 2005-03-31 | 2014-01-08 | 積水化学工業株式会社 | 無機微粒子分散ペースト組成物 |
| US8158037B2 (en) | 2005-04-08 | 2012-04-17 | Johnson & Johnson Vision Care, Inc. | Photochromic materials having extended pi-conjugated systems and compositions and articles including the same |
| US8647538B2 (en) | 2005-04-08 | 2014-02-11 | Transitions Optical, Inc. | Photochromic compounds having at least two photochromic moieties |
| US20060227287A1 (en) * | 2005-04-08 | 2006-10-12 | Frank Molock | Photochromic ophthalmic devices made with dual initiator system |
| US9028728B2 (en) | 2005-04-08 | 2015-05-12 | Transitions Optical, Inc. | Photochromic materials that include indeno-fused naphthopyrans |
| US9139552B2 (en) | 2005-04-08 | 2015-09-22 | Transitions Optical, Inc. | Indeno-fused naphthopyrans having ethylenically unsaturated groups |
| US20060228557A1 (en) * | 2005-04-08 | 2006-10-12 | Beon-Kyu Kim | Photochromic materials having extended pi-conjugated systems and compositions and articles including the same |
| US9052438B2 (en) | 2005-04-08 | 2015-06-09 | Johnson & Johnson Vision Care, Inc. | Ophthalmic devices comprising photochromic materials with reactive substituents |
| US7556750B2 (en) | 2005-04-08 | 2009-07-07 | Transitions Optical, Inc. | Photochromic materials with reactive substituents |
| MY146558A (en) * | 2005-08-09 | 2012-08-30 | Coopervision Int Holding Co Lp | Compositions and methods for producing silicone hydrogel contact lenses |
| US20070048249A1 (en) | 2005-08-24 | 2007-03-01 | Purdue Research Foundation | Hydrophilized bactericidal polymers |
| US8343473B2 (en) | 2005-08-24 | 2013-01-01 | Purdue Research Foundation | Hydrophilized antimicrobial polymers |
| WO2007041166A2 (en) | 2005-09-30 | 2007-04-12 | The Lagado Corporation | Highly oxygen permeable rigid contact lenses from polyacetylenes |
| US7723422B2 (en) * | 2005-12-23 | 2010-05-25 | Boston Scientific Scimed, Inc. | Functionalized block copolymers |
| US20070185014A1 (en) * | 2006-02-09 | 2007-08-09 | The Schepens Eye Research Institute, Inc. | Methods and compositions for modulating conjunctival goblet cells |
| US20070212556A1 (en) * | 2006-03-07 | 2007-09-13 | Musa Osama M | Curable materials containing siloxane |
| US20070257387A1 (en) * | 2006-05-05 | 2007-11-08 | Hofmann Gregory J | Package mold combination |
| US20080001320A1 (en) * | 2006-06-28 | 2008-01-03 | Knox Wayne H | Optical Material and Method for Modifying the Refractive Index |
| US8569538B2 (en) * | 2006-06-30 | 2013-10-29 | Johnson & Johnson Vision Care, Inc. | Acryloyl materials for molded plastics |
| US7960465B2 (en) | 2006-06-30 | 2011-06-14 | Johnson & Johnson Vision Care, Inc. | Antimicrobial lenses, processes to prepare them and methods of their use |
| US8053539B2 (en) | 2006-06-30 | 2011-11-08 | Johnson & Johnson Vision Care Inc. | Siloxanyl materials for molded plastics |
| US9056880B2 (en) | 2006-09-29 | 2015-06-16 | Johnson & Johnson Vision Care, Inc. | Process for producing hydrolysis-resistant silicone compounds |
| US7838698B2 (en) | 2006-09-29 | 2010-11-23 | Johnson & Johnson Vision Care, Inc. | Hydrolysis-resistant silicone compounds |
| US20080081850A1 (en) * | 2006-09-29 | 2008-04-03 | Kazuhiko Fujisawa | Process for producing hydrolysis-resistant silicone compounds |
| US20080251958A1 (en) * | 2006-10-31 | 2008-10-16 | Molock Frank F | Light absorbing prepolymers for use in tinted contact lenses and methods for their production |
| US20080119627A1 (en) * | 2006-11-22 | 2008-05-22 | Masataka Nakamura | Methods for purifying siloxanyl monomers |
| WO2008079916A2 (en) * | 2006-12-21 | 2008-07-03 | Novartis Ag | High intensity uv mold pretreatment |
| US8690319B2 (en) | 2007-05-21 | 2014-04-08 | Johnson & Johnson Vision Care, Inc. | Ophthalmic lenses for prevention of myopia progression |
| US8080622B2 (en) * | 2007-06-29 | 2011-12-20 | Johnson & Johnson Vision Care, Inc. | Soluble silicone prepolymers |
| US8968396B2 (en) | 2007-07-23 | 2015-03-03 | Powervision, Inc. | Intraocular lens delivery systems and methods of use |
| AU2008279167B2 (en) | 2007-07-23 | 2014-10-09 | Alcon Inc. | Post-implant lens power modification |
| US9610155B2 (en) | 2008-07-23 | 2017-04-04 | Powervision, Inc. | Intraocular lens loading systems and methods of use |
| US8956408B2 (en) | 2007-07-23 | 2015-02-17 | Powervision, Inc. | Lens delivery system |
| WO2009015226A2 (en) | 2007-07-23 | 2009-01-29 | Powervision, Inc. | Accommodating intraocular lenses and methods of use |
| US8314927B2 (en) | 2007-07-23 | 2012-11-20 | Powervision, Inc. | Systems and methods for testing intraocular lenses |
| US8318055B2 (en) | 2007-08-21 | 2012-11-27 | Johnson & Johnson Vision Care, Inc. | Methods for formation of an ophthalmic lens precursor and lens |
| US8317505B2 (en) | 2007-08-21 | 2012-11-27 | Johnson & Johnson Vision Care, Inc. | Apparatus for formation of an ophthalmic lens precursor and lens |
| US8313828B2 (en) | 2008-08-20 | 2012-11-20 | Johnson & Johnson Vision Care, Inc. | Ophthalmic lens precursor and lens |
| US7625086B2 (en) | 2007-08-28 | 2009-12-01 | Johnson & Johnson Vision Care, Inc. | Method of designing multifocal contact lenses |
| US20090111905A1 (en) * | 2007-10-31 | 2009-04-30 | Ture Kindt-Larsen | Process for forming random (meth)acrylate containing prepolymers |
| US7897654B2 (en) * | 2007-12-27 | 2011-03-01 | Johnson & Johnson Vision Care Inc. | Silicone prepolymer solutions |
| DE102008006654A1 (de) * | 2008-01-30 | 2009-08-06 | Biotronik Vi Patent Ag | Implantat mit einem Grundkörper aus einer biokorrodierbaren Legierung |
| US7753521B2 (en) | 2008-03-31 | 2010-07-13 | Johnson & Johnson Vision Care, Inc. | Lenses for the correction of presbyopia and methods of designing the lenses |
| CA2738232A1 (en) * | 2008-10-03 | 2010-04-08 | Momentive Performance Materials Inc. | Hydrophilic silicone monomers, process for their preparation and thin films containing the same |
| US10299913B2 (en) | 2009-01-09 | 2019-05-28 | Powervision, Inc. | Accommodating intraocular lenses and methods of use |
| WO2010133680A1 (en) * | 2009-05-22 | 2010-11-25 | Novartis Ag | Actinically-crosslinkable siloxane-containing copolymers |
| EP2432821B1 (en) * | 2009-05-22 | 2017-08-30 | Novartis AG | Actinically-crosslinkable siloxane-containing copolymers |
| WO2011026068A2 (en) * | 2009-08-31 | 2011-03-03 | Powervision, Inc. | Lens capsule size estimation |
| MY159465A (en) * | 2009-10-01 | 2017-01-13 | Coopervision Int Holding Co Lp | Silicone hydrogel contact lenses and methods of making silicone hydrogel contact lenses |
| KR101212668B1 (ko) * | 2009-11-20 | 2012-12-14 | 제일모직주식회사 | 고분자, 보호막 조성물 및 이를 이용한 패턴 형성 방법 |
| JP5764925B2 (ja) * | 2009-12-28 | 2015-08-19 | 東レ株式会社 | シリコーンプレポリマーの製造方法 |
| EP2539351B1 (en) | 2010-02-23 | 2017-07-12 | PowerVision, Inc. | Fluid for accommodating intraocular lenses |
| WO2012006616A2 (en) | 2010-07-09 | 2012-01-12 | Powervision, Inc. | Intraocular lens delivery devices and methods of use |
| WO2012016097A2 (en) | 2010-07-30 | 2012-02-02 | Novartis Ag | Amphiphilic polysiloxane prepolymers and uses thereof |
| CA2813469C (en) | 2010-10-06 | 2016-01-12 | Novartis Ag | Polymerizable chain-extended polysiloxanes with pendant hydrophilic groups |
| CA2811013C (en) | 2010-10-06 | 2016-01-19 | Novartis Ag | Chain-extended polysiloxane crosslinkers with dangling hydrophilic polymer chains |
| WO2012047969A1 (en) | 2010-10-06 | 2012-04-12 | Novartis Ag | Water-processable silicone-containing prepolymers and uses thereof |
| TWI421306B (zh) * | 2011-02-21 | 2014-01-01 | Far Eastern New Century Corp | 具有高含水率之聚矽氧水膠 |
| US8992012B2 (en) | 2011-06-23 | 2015-03-31 | Johnson & Johnson Vision Care, Inc. | Lens systems for presbyopia |
| US10433949B2 (en) | 2011-11-08 | 2019-10-08 | Powervision, Inc. | Accommodating intraocular lenses |
| JP5927014B2 (ja) | 2012-04-18 | 2016-05-25 | Hoya株式会社 | 湿潤性表面を有するシリコーンハイドロゲルソフトコンタクトレンズ |
| WO2014070792A1 (en) | 2012-10-29 | 2014-05-08 | Ariste Medical, Inc. | Polymer coating compositions and coated products |
| CN104937011B (zh) * | 2013-01-18 | 2020-12-29 | 巴斯夫欧洲公司 | 具有聚二甲基硅氧烷嵌段的嵌段共聚物 |
| EP3785668A1 (en) | 2013-03-15 | 2021-03-03 | Alcon Inc. | Intraocular lens storage and loading devices and methods of use |
| WO2015164524A1 (en) | 2014-04-22 | 2015-10-29 | Ariste Medical, Inc. | Methods and processes for application of drug delivery polymeric coatings |
| US9645412B2 (en) | 2014-11-05 | 2017-05-09 | Johnson & Johnson Vision Care Inc. | Customized lens device and method |
| US20180153682A1 (en) | 2015-06-10 | 2018-06-07 | Powervision, Inc. | Intraocular lens materials and components |
| CN108348328B (zh) | 2015-11-06 | 2020-04-10 | 力景公司 | 可调节人工晶状体和制造方法 |
| US10359643B2 (en) | 2015-12-18 | 2019-07-23 | Johnson & Johnson Vision Care, Inc. | Methods for incorporating lens features and lenses having such features |
| CN108368118B (zh) * | 2016-06-07 | 2021-03-02 | 深圳市塔吉瑞生物医药有限公司 | 一种取代的稠合咪唑环化合物及其药物组合物 |
| JP7067991B2 (ja) * | 2017-03-29 | 2022-05-16 | 住友化学株式会社 | イソインドリン色素の製造方法 |
| US20180340046A1 (en) | 2017-05-27 | 2018-11-29 | Poly Group LLC | Dispersible antimicrobial complex and coatings therefrom |
| US20180362678A1 (en) | 2017-06-16 | 2018-12-20 | Poly Group LLC | Polymeric antimicrobial surfactant |
| BR112022005526A2 (pt) | 2019-10-04 | 2022-06-21 | Alcon Inc | Lentes intraoculares ajustáveis e métodos de ajuste pós-operatório de lentes intraoculares |
| US20220409351A1 (en) * | 2019-11-22 | 2022-12-29 | Emanate Biomedical, Inc. | Oral appliance for delivery of an antimicrobial composition |
| US11364696B2 (en) | 2020-09-18 | 2022-06-21 | Johnson & Johnson Vision Care, Inc | Apparatus for forming an ophthalmic lens |
| CN112480308B (zh) * | 2020-11-25 | 2022-03-18 | 复旦大学 | 一种智能水凝胶及其制备方法 |
| CN116157720A (zh) * | 2020-12-25 | 2023-05-23 | 三井化学株式会社 | 异（硫）氰酸酯化合物、光学材料用聚合性组合物、成型体、光学材料、塑料透镜、塑料偏光透镜、异（硫）氰酸酯化合物的制造方法、光学材料用聚合性组合物的制造方法、光学材料的制造方法及塑料偏光透镜的制造方法 |
| BR112023018612A2 (pt) | 2021-04-06 | 2023-10-24 | Alcon Inc | Aparelho, sistemas e métodos para avaliar objetivamente a acomodação em um olho |
| KR102641709B1 (ko) * | 2023-05-22 | 2024-02-29 | 단국대학교 천안캠퍼스 산학협력단 | 자가치유 가교제 화합물 및 이를 포함하는 렌즈용 또는 렌즈 복원용 하이드로겔 |
Family Cites Families (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4323636A (en) * | 1971-04-01 | 1982-04-06 | E. I. Du Pont De Nemours And Company | Photosensitive block copolymer composition and elements |
| US3916033A (en) * | 1971-06-09 | 1975-10-28 | High Voltage Engineering Corp | Contact lens |
| US3854982A (en) * | 1972-05-12 | 1974-12-17 | Hydroplastics Inc | Method for preparing hydrophilic polymer grafts including irradiation |
| US3948841A (en) * | 1972-05-22 | 1976-04-06 | Karel Dusek | Process for producing transparent gels with improved mechanical and sorption properties from copolymers of 2-hydroxyethyl methacrylate and amides of acrylic or methacrylic acid |
| JPS584327B2 (ja) * | 1978-07-15 | 1983-01-26 | 東洋コンタクトレンズ株式会社 | コンタクトレンズ |
| JPS5455455A (en) * | 1977-10-12 | 1979-05-02 | Toyo Contact Lens Co Ltd | Contact lens |
| JPS5466853A (en) | 1977-11-08 | 1979-05-29 | Toyo Contact Lens Co Ltd | Soft contact lens |
| US4264489A (en) * | 1980-01-14 | 1981-04-28 | Den-Mat, Inc. | Provisional crown-and-bridge resin containing tetrahydrofuryl methacrylate |
| US4698373A (en) * | 1981-01-21 | 1987-10-06 | Dentsply Research & Development Corp. | Stable one part dental compositions employing ipn technology |
| US4495313A (en) * | 1981-04-30 | 1985-01-22 | Mia Lens Production A/S | Preparation of hydrogel for soft contact lens with water displaceable boric acid ester |
| DE3137416A1 (de) * | 1981-09-19 | 1983-03-31 | Basf Ag, 6700 Ludwigshafen | Fotopolymerisierbare gemische und elemente daraus |
| US4510593A (en) | 1982-10-18 | 1985-04-09 | Minnesota Mining And Manufacturing Company | Information disk of grooved, metal-coated crosslinked polymeric layer |
| US4618659A (en) * | 1984-12-05 | 1986-10-21 | Ppg Industries, Inc. | Low molecular weight acrylic polymers |
| JPS61228438A (ja) * | 1985-04-02 | 1986-10-11 | Konishiroku Photo Ind Co Ltd | 感光性組成物 |
| US4711943A (en) * | 1985-04-26 | 1987-12-08 | Sola U.S.A. Inc. | Hydrophilic siloxane monomers and dimers for contact lens materials, and contact lenses fabricated therefrom |
| DE3517615C2 (de) * | 1985-05-15 | 1987-04-09 | Titmus Eurocon Kontaktlinsen GmbH, 8750 Aschaffenburg | Verfahren zur Hydrophilierung eines Siliconkautschukformkörpers an seiner Oberfläche |
| CA1296121C (en) | 1986-02-27 | 1992-02-18 | Lori J. Klingler | Uv or heat curable reinforced elastomer compositions |
| US4963159A (en) * | 1987-11-24 | 1990-10-16 | Schering Corporation | Hydrophilic colored contact lens |
| US4978713A (en) | 1987-12-16 | 1990-12-18 | Ciba-Geigy Corporation | Polyvinyl alcohol derivatives containing pendant vinylic monomer reaction product units bound through ether groups and hydrogel contact lenses made therefrom |
| US4910277A (en) * | 1988-02-09 | 1990-03-20 | Bambury Ronald E | Hydrophilic oxygen permeable polymers |
| US4889664A (en) * | 1988-11-25 | 1989-12-26 | Vistakon, Inc. | Method of forming shaped hydrogel articles including contact lenses |
| US5039459A (en) * | 1988-11-25 | 1991-08-13 | Johnson & Johnson Vision Products, Inc. | Method of forming shaped hydrogel articles including contact lenses |
| US5070215A (en) * | 1989-05-02 | 1991-12-03 | Bausch & Lomb Incorporated | Novel vinyl carbonate and vinyl carbamate contact lens material monomers |
| US5034461A (en) * | 1989-06-07 | 1991-07-23 | Bausch & Lomb Incorporated | Novel prepolymers useful in biomedical devices |
| US5002794A (en) * | 1989-08-31 | 1991-03-26 | The Board Of Regents Of The University Of Washington | Method of controlling the chemical structure of polymeric films by plasma |
| KR920701271A (ko) | 1989-09-14 | 1992-08-11 | 메이-자이 창 | 개선된 임상성능을 갖는 기체 투과성 소프트 콘택트렌즈 |
| US5080839A (en) | 1990-04-17 | 1992-01-14 | Johnson & Johnson Vision Products, Inc. | Process for hydrating soft contact lenses |
| JP2961804B2 (ja) * | 1990-04-18 | 1999-10-12 | 大日本インキ化学工業株式会社 | 塗料用樹脂組成物 |
| US5170192A (en) * | 1990-11-29 | 1992-12-08 | Pilkington Visioncare, Inc. | Oxygen permeable bifocal contact lenses and their manufacture |
| GB9115683D0 (en) | 1991-07-19 | 1991-09-04 | Ici Plc | Polymerisable composition |
| JP3176461B2 (ja) * | 1991-12-13 | 2001-06-18 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | 共重合体を基材とする結合剤 |
| US5944853A (en) | 1992-10-26 | 1999-08-31 | Johnson & Johnson Vision Products, Inc. | Method for preparing halotriazine dye- and vinyl sulfone dye-monomer compounds |
| TW228529B (enExample) * | 1992-12-23 | 1994-08-21 | Ciba Geigy | |
| DK0637491T3 (da) | 1993-07-29 | 1998-07-27 | Novartis Ag | Fremgangsmåde og apparat til fremstilling af formlegemer. |
| TW272976B (enExample) * | 1993-08-06 | 1996-03-21 | Ciba Geigy Ag | |
| US6743438B2 (en) | 1993-10-26 | 2004-06-01 | Pbh, Inc. | Colored contact lenses and method of making same |
| US6407145B1 (en) | 1994-08-04 | 2002-06-18 | Novartis Ag | Photocrosslinkable materials and applications |
| AU4438696A (en) | 1995-02-03 | 1996-08-21 | Novartis Ag | Crosslinked polymers |
| WO1996024075A1 (en) * | 1995-02-03 | 1996-08-08 | Novartis Ag | Crosslinked polymers containing ester or amide groups |
| US5807937A (en) * | 1995-11-15 | 1998-09-15 | Carnegie Mellon University | Processes based on atom (or group) transfer radical polymerization and novel (co) polymers having useful structures and properties |
| US5779943A (en) * | 1996-03-19 | 1998-07-14 | Johnson & Johnson Vision Products, Inc. | Molded polymeric object with wettable surface made from latent-hydrophilic monomers |
| ID17663A (id) | 1996-07-26 | 1998-01-15 | Novartis Ag | Pembuatan cetakan-cetakan |
| SG54538A1 (en) | 1996-08-05 | 1998-11-16 | Hoya Corp | Soft contact lens with high moisture content and method for producing the same |
| CA2282090A1 (en) | 1997-03-25 | 1998-10-01 | Novartis Ag | Molding processes |
| TW429327B (en) | 1997-10-21 | 2001-04-11 | Novartis Ag | Single mould alignment |
| US6822016B2 (en) | 2001-09-10 | 2004-11-23 | Johnson & Johnson Vision Care, Inc. | Biomedical devices containing internal wetting agents |
| US5998498A (en) * | 1998-03-02 | 1999-12-07 | Johnson & Johnson Vision Products, Inc. | Soft contact lenses |
| US6087415A (en) * | 1998-06-11 | 2000-07-11 | Johnson & Johnson Vision Care, Inc. | Biomedical devices with hydrophilic coatings |
| BR9914457A (pt) | 1998-09-22 | 2001-10-16 | Zms Lic | Processo de polimerização em formato aproximado de rede e materiais apropriados para seu uso |
| US6592814B2 (en) * | 1998-10-02 | 2003-07-15 | Johnson & Johnson Vision Care, Inc. | Biomedical devices with antimicrobial coatings |
| US5981675A (en) * | 1998-12-07 | 1999-11-09 | Bausch & Lomb Incorporated | Silicone-containing macromonomers and low water materials |
| DE19903391A1 (de) * | 1999-01-29 | 2000-08-03 | Bayer Ag | Wäßriges Überzugsmittel, Verfahren zu seiner Herstellung und seine Verwendung |
| CA2368168C (en) | 1999-03-16 | 2007-10-30 | David S. Soane | Precision integral articles |
| US6416690B1 (en) * | 2000-02-16 | 2002-07-09 | Zms, Llc | Precision composite lens |
| US6419858B1 (en) * | 2000-06-13 | 2002-07-16 | Zms, Llc | Morphology trapping and materials suitable for use therewith |
| US6610801B1 (en) * | 2000-11-13 | 2003-08-26 | Rohmax Additives Gmbh | Processes for synthesis of polymer compositions |
| US6545097B2 (en) | 2000-12-12 | 2003-04-08 | Scimed Life Systems, Inc. | Drug delivery compositions and medical devices containing block copolymer |
| SG102670A1 (en) | 2001-03-27 | 2004-03-26 | Johnson & Johnson Vision Care | Method and apparatus for washing or hydration of ophthalmic devices |
| US20030020870A1 (en) | 2001-06-27 | 2003-01-30 | Zms, Llc | Biomedical molding materials from semi-solid precursors |
| JP2003064132A (ja) * | 2001-08-28 | 2003-03-05 | Nof Corp | 重合体、製造方法および乳化・分散剤 |
| US20060100408A1 (en) | 2002-03-11 | 2006-05-11 | Powell P M | Method for forming contact lenses comprising therapeutic agents |
| US6846892B2 (en) | 2002-03-11 | 2005-01-25 | Johnson & Johnson Vision Care, Inc. | Low polydispersity poly-HEMA compositions |
| US6709103B1 (en) * | 2002-10-31 | 2004-03-23 | Johnson & Johnson Vision Care, Inc. | Methods for designing multifocal ophthalmic lenses |
-
2003
- 2003-02-14 US US10/367,253 patent/US6846892B2/en not_active Expired - Lifetime
- 2003-03-06 DE DE60334146T patent/DE60334146D1/de not_active Expired - Lifetime
- 2003-03-06 JP JP2003575849A patent/JP5220260B2/ja not_active Expired - Fee Related
- 2003-03-06 WO PCT/US2003/006835 patent/WO2003077792A2/en not_active Ceased
- 2003-03-06 CA CA2478307A patent/CA2478307C/en not_active Expired - Fee Related
- 2003-03-06 KR KR1020047014200A patent/KR100899364B1/ko not_active Expired - Fee Related
- 2003-03-06 EP EP03721337A patent/EP1567567B1/en not_active Revoked
- 2003-03-06 AU AU2003224658A patent/AU2003224658B2/en not_active Ceased
- 2003-03-06 BR BRPI0317545A patent/BRPI0317545A2/pt not_active IP Right Cessation
- 2003-03-11 AR ARP030100835A patent/AR038934A1/es not_active Application Discontinuation
- 2003-03-11 TW TW092105145A patent/TWI325868B/zh not_active IP Right Cessation
-
2004
- 2004-11-08 US US10/983,851 patent/US7256246B2/en not_active Expired - Lifetime
-
2007
- 2007-07-06 US US11/774,453 patent/US7816460B2/en not_active Expired - Lifetime
-
2009
- 2009-03-18 AR ARP090100972A patent/AR070938A2/es not_active Application Discontinuation
- 2009-07-06 JP JP2009159594A patent/JP5697317B2/ja not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5220260B2 (ja) | 低多分散性ポリｈｅｍａ組成物 | |
| JP2005539098A5 (enExample) | ||
| TWI432229B (zh) | 含有兩性嵌段共聚物之生醫裝置 | |
| EP1216142A1 (en) | Thermoformable ophthalmic lens | |
| EP1852246A2 (en) | Package-mold combination | |
| EP2207825B8 (en) | Process for forming random (meth)acrylate containing prepolymers | |
| EP2232304B1 (en) | Method for making silicone hydrogel contact lenses | |
| CN1320004C (zh) | 低多分散性聚甲基丙烯酸2－羟乙酯组合物 | |
| HK1079225B (en) | Low polydispersity poly-hema compositions | |
| CN116490532B (zh) | 眼科器件用改性剂 | |
| JP7357055B2 (ja) | 高含水量眼科デバイス | |
| HK40071111A (en) | Amino acid-based polymerizable compounds and ophthalmic devices prepared therefrom | |
| HK1109882A (en) | Package-mold combination |