DE69623647T2 - Polyurethane aus polysiloxan-polyol-makromeren - Google Patents
Polyurethane aus polysiloxan-polyol-makromerenInfo
- Publication number
- DE69623647T2 DE69623647T2 DE69623647T DE69623647T DE69623647T2 DE 69623647 T2 DE69623647 T2 DE 69623647T2 DE 69623647 T DE69623647 T DE 69623647T DE 69623647 T DE69623647 T DE 69623647T DE 69623647 T2 DE69623647 T2 DE 69623647T2
- Authority
- DE
- Germany
- Prior art keywords
- diisocyanate
- polymer
- segment
- carbon atoms
- macromer
- 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.)
- Expired - Lifetime
Links
- 229920005862 polyol Polymers 0.000 title claims abstract description 41
- 239000004814 polyurethane Substances 0.000 title description 2
- 229920002635 polyurethane Polymers 0.000 title description 2
- -1 polysiloxane Polymers 0.000 claims abstract description 123
- 229920000642 polymer Polymers 0.000 claims abstract description 87
- 238000000034 method Methods 0.000 claims abstract description 39
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 39
- 150000003077 polyols Chemical class 0.000 claims abstract description 33
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 32
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
- 230000008569 process Effects 0.000 claims abstract description 19
- 238000000576 coating method Methods 0.000 claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 210000004087 cornea Anatomy 0.000 claims abstract description 11
- 239000011248 coating agent Substances 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 239000007943 implant Substances 0.000 claims description 38
- 125000005442 diisocyanate group Chemical group 0.000 claims description 27
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 25
- 230000003287 optical effect Effects 0.000 claims description 23
- 125000002947 alkylene group Chemical group 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 22
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 22
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 19
- 150000001720 carbohydrates Chemical class 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 239000011148 porous material Substances 0.000 claims description 12
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 11
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 11
- 230000009257 reactivity Effects 0.000 claims description 11
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 239000012530 fluid Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 230000002829 reductive effect Effects 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000000686 lactone group Chemical group 0.000 claims description 5
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims description 4
- LFHITXHDBPEMEZ-UHFFFAOYSA-N 3-isocyanatopropyl-[3-isocyanatopropyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound O=C=NCCC[Si](C)(C)O[Si](C)(C)CCCN=C=O LFHITXHDBPEMEZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 230000012010 growth Effects 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 4
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 4
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 claims description 3
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 claims description 3
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 claims description 3
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 claims description 3
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 claims description 3
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 claims description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 3
- 230000010261 cell growth Effects 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical group O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 230000036961 partial effect Effects 0.000 claims description 2
- 125000005103 alkyl silyl group Chemical group 0.000 claims 3
- 235000004252 protein component Nutrition 0.000 claims 1
- 230000008467 tissue growth Effects 0.000 claims 1
- 230000004304 visual acuity Effects 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 29
- 239000002243 precursor Substances 0.000 abstract description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 29
- 150000003254 radicals Chemical class 0.000 description 29
- 239000000203 mixture Substances 0.000 description 28
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 22
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 21
- 239000004205 dimethyl polysiloxane Substances 0.000 description 20
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 229910052760 oxygen Inorganic materials 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 15
- 239000001301 oxygen Substances 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- 125000003277 amino group Chemical group 0.000 description 14
- 238000004132 cross linking Methods 0.000 description 14
- 230000035699 permeability Effects 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 10
- 239000012975 dibutyltin dilaurate Substances 0.000 description 10
- 210000001519 tissue Anatomy 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229910052786 argon Inorganic materials 0.000 description 9
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 9
- 150000002596 lactones Chemical class 0.000 description 9
- 238000004448 titration Methods 0.000 description 9
- JCZPMGDSEAFWDY-SQOUGZDYSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanamide Chemical compound NC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO JCZPMGDSEAFWDY-SQOUGZDYSA-N 0.000 description 8
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 8
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- 229920000858 Cyclodextrin Polymers 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 7
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
- 150000001335 aliphatic alkanes Chemical class 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 235000012209 glucono delta-lactone Nutrition 0.000 description 7
- 229960003681 gluconolactone Drugs 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000004372 Polyvinyl alcohol Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000006459 hydrosilylation reaction Methods 0.000 description 6
- FSICMNGKCHFHGP-AMTLMPIISA-N lactobiono-1,5-lactone Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(=O)[C@H](O)[C@H]1O FSICMNGKCHFHGP-AMTLMPIISA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 229920002451 polyvinyl alcohol Polymers 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- ZKJNETINGMOHJG-GGWOSOGESA-N (e)-1-[(e)-prop-1-enoxy]prop-1-ene Chemical class C\C=C\O\C=C\C ZKJNETINGMOHJG-GGWOSOGESA-N 0.000 description 4
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 4
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 229940080345 gamma-cyclodextrin Drugs 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 230000000670 limiting effect Effects 0.000 description 4
- 229920002521 macromolecule Polymers 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 229920000307 polymer substrate Polymers 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 230000008707 rearrangement Effects 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000004381 surface treatment Methods 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- 238000000214 vapour pressure osmometry Methods 0.000 description 4
- NNKCVJYUFBVOMM-MJCJSMLMSA-N (1s,2s,5s,8s)-2,3,8-trihydroxy-4,7-dioxabicyclo[3.2.1]octan-6-one Chemical compound O[C@@H]1C(O)O[C@@H]2C(=O)O[C@H]1[C@@H]2O NNKCVJYUFBVOMM-MJCJSMLMSA-N 0.000 description 3
- GPVGUNIIVWJTLK-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-prop-2-enoxyoctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCOCC=C GPVGUNIIVWJTLK-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910001369 Brass Inorganic materials 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
- UYUXSRADSPPKRZ-SKNVOMKLSA-N D-glucurono-6,3-lactone Chemical compound O=C[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O UYUXSRADSPPKRZ-SKNVOMKLSA-N 0.000 description 3
- KXTCDGRHGVMZOH-SLVMBWJPSA-N D-maltoheptaono-1,5-lactone Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@@H](O[C@H]7[C@H](O)[C@@H](O)C(=O)O[C@@H]7CO)O[C@@H]6CO)O[C@@H]5CO)O[C@@H]4CO)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O KXTCDGRHGVMZOH-SLVMBWJPSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229930195725 Mannitol Natural products 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000004809 Teflon Substances 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 3
- OSLGKRDOEMLAJV-UHFFFAOYSA-N benzyl n-prop-2-enylcarbamate Chemical compound C=CCNC(=O)OCC1=CC=CC=C1 OSLGKRDOEMLAJV-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 239000010951 brass Substances 0.000 description 3
- 229920006037 cross link polymer Polymers 0.000 description 3
- 229940097362 cyclodextrins Drugs 0.000 description 3
- 239000012632 extractable Substances 0.000 description 3
- WTXGYGWMPUGBAL-MGCNEYSASA-N galactonolactone Chemical compound O[C@@H]1COC(=O)[C@H](O)[C@@H](O)[C@H]1O WTXGYGWMPUGBAL-MGCNEYSASA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000000594 mannitol Substances 0.000 description 3
- 235000010355 mannitol Nutrition 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 210000002536 stromal cell Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003538 tetroses Chemical class 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 210000003556 vascular endothelial cell Anatomy 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@H](CO)O[C@@H](O[C@@H]2[C@@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 0.000 description 1
Classifications
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/61—Polysiloxanes
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Physics & Mathematics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Silicon Polymers (AREA)
- Materials For Medical Uses (AREA)
- Eyeglasses (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP95810818 | 1995-12-22 | ||
| PCT/EP1996/005507 WO1997023532A1 (en) | 1995-12-22 | 1996-12-10 | Polyurethanes made from polysiloxane/polyol macromers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69623647D1 DE69623647D1 (en) | 2002-10-17 |
| DE69623647T2 true DE69623647T2 (de) | 2003-05-28 |
Family
ID=8221837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69623647T Expired - Lifetime DE69623647T2 (de) | 1995-12-22 | 1996-12-10 | Polyurethane aus polysiloxan-polyol-makromeren |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6271332B1 (https=) |
| EP (1) | EP0868457B1 (https=) |
| JP (1) | JP2000506554A (https=) |
| AT (1) | ATE223933T1 (https=) |
| AU (1) | AU1369397A (https=) |
| DE (1) | DE69623647T2 (https=) |
| WO (1) | WO1997023532A1 (https=) |
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| US8527026B2 (en) | 1997-03-04 | 2013-09-03 | Dexcom, Inc. | Device and method for determining analyte levels |
| US6001067A (en) | 1997-03-04 | 1999-12-14 | Shults; Mark C. | Device and method for determining analyte levels |
| AU732188B2 (en) | 1997-08-13 | 2001-04-12 | Surx, Inc. | Noninvasive devices, methods, and systems for shrinking of tissues |
| US9023031B2 (en) | 1997-08-13 | 2015-05-05 | Verathon Inc. | Noninvasive devices, methods, and systems for modifying tissues |
| US6849671B2 (en) | 1998-03-02 | 2005-02-01 | Johnson & Johnson Vision Care, Inc. | Contact lenses |
| FR2779940B1 (fr) * | 1998-06-19 | 2000-11-03 | Ioltechnologie Production | Implant formant lentille intraoculaire monobloc bi-materiaux |
| US6599559B1 (en) * | 2000-04-03 | 2003-07-29 | Bausch & Lomb Incorporated | Renewable surface treatment of silicone medical devices with reactive hydrophilic polymers |
| US7306591B2 (en) | 2000-10-02 | 2007-12-11 | Novasys Medical, Inc. | Apparatus and methods for treating female urinary incontinence |
| US20030032874A1 (en) | 2001-07-27 | 2003-02-13 | Dexcom, Inc. | Sensor head for use with implantable devices |
| US8364229B2 (en) | 2003-07-25 | 2013-01-29 | Dexcom, Inc. | Analyte sensors having a signal-to-noise ratio substantially unaffected by non-constant noise |
| US7828728B2 (en) | 2003-07-25 | 2010-11-09 | Dexcom, Inc. | Analyte sensor |
| US7613491B2 (en) | 2002-05-22 | 2009-11-03 | Dexcom, Inc. | Silicone based membranes for use in implantable glucose sensors |
| US7226978B2 (en) | 2002-05-22 | 2007-06-05 | Dexcom, Inc. | Techniques to improve polyurethane membranes for implantable glucose sensors |
| US9763609B2 (en) | 2003-07-25 | 2017-09-19 | Dexcom, Inc. | Analyte sensors having a signal-to-noise ratio substantially unaffected by non-constant noise |
| EP1648298A4 (en) | 2003-07-25 | 2010-01-13 | Dexcom Inc | OXYGEN-IMPROVED MEMBRANE SYSTEMS FOR IMPLANTABLE DEVICES |
| US7591801B2 (en) | 2004-02-26 | 2009-09-22 | Dexcom, Inc. | Integrated delivery device for continuous glucose sensor |
| US7920906B2 (en) | 2005-03-10 | 2011-04-05 | Dexcom, Inc. | System and methods for processing analyte sensor data for sensor calibration |
| US9247900B2 (en) | 2004-07-13 | 2016-02-02 | Dexcom, Inc. | Analyte sensor |
| EP1732973A1 (en) * | 2004-02-23 | 2006-12-20 | E.I.Du pont de nemours and company | Crosslinked polymers containing biomass derived materials |
| WO2009048462A1 (en) | 2007-10-09 | 2009-04-16 | Dexcom, Inc. | Integrated insulin delivery system with continuous glucose sensor |
| US8808228B2 (en) | 2004-02-26 | 2014-08-19 | Dexcom, Inc. | Integrated medicament delivery device for use with continuous analyte sensor |
| US8277713B2 (en) | 2004-05-03 | 2012-10-02 | Dexcom, Inc. | Implantable analyte sensor |
| US8989833B2 (en) | 2004-07-13 | 2015-03-24 | Dexcom, Inc. | Transcutaneous analyte sensor |
| US20060200245A1 (en) * | 2005-03-07 | 2006-09-07 | Sdgi Holdings, Inc. | Materials, devices, and methods for in-situ formation of composite intervertebral implants |
| US8133178B2 (en) | 2006-02-22 | 2012-03-13 | Dexcom, Inc. | Analyte sensor |
| US8744546B2 (en) | 2005-05-05 | 2014-06-03 | Dexcom, Inc. | Cellulosic-based resistance domain for an analyte sensor |
| US20200037875A1 (en) | 2007-05-18 | 2020-02-06 | Dexcom, Inc. | Analyte sensors having a signal-to-noise ratio substantially unaffected by non-constant noise |
| US20080306444A1 (en) | 2007-06-08 | 2008-12-11 | Dexcom, Inc. | Integrated medicament delivery device for use with continuous analyte sensor |
| US8583204B2 (en) | 2008-03-28 | 2013-11-12 | Dexcom, Inc. | Polymer membranes for continuous analyte sensors |
| US11730407B2 (en) | 2008-03-28 | 2023-08-22 | Dexcom, Inc. | Polymer membranes for continuous analyte sensors |
| US8682408B2 (en) | 2008-03-28 | 2014-03-25 | Dexcom, Inc. | Polymer membranes for continuous analyte sensors |
| EP4549933A3 (en) | 2008-09-19 | 2025-05-21 | DexCom, Inc. | Particle-containing membrane and particulate electrode for analyte sensors |
| US8480227B2 (en) | 2010-07-30 | 2013-07-09 | Novartis Ag | Silicone hydrogel lenses with water-rich surfaces |
| HUE029018T2 (en) | 2011-10-12 | 2017-02-28 | Novartis Ag | A method for producing UV absorbing contact lenses by coating |
| US9974646B2 (en) | 2012-09-05 | 2018-05-22 | University Of Miami | Keratoprosthesis, and system and method of corneal repair using same |
| HUE031702T2 (en) | 2012-12-17 | 2017-07-28 | Novartis Ag | A method for producing improved UV absorbing ophthalmic lenses |
| HUE038809T2 (hu) | 2013-12-17 | 2018-11-28 | Novartis Ag | Térhálósított hidrofíl bevonattal ellátott szilikon hidrogél lencse |
| EP3122828B1 (en) | 2014-03-26 | 2025-10-15 | 3M Innovative Properties Company | Polyurethane compositions, films, and methods thereof |
| MY183678A (en) | 2014-08-26 | 2021-03-08 | Alcon Inc | Method for applying stable coating on silicone hydrogel contact lenses |
| KR102604468B1 (ko) | 2015-12-15 | 2023-11-22 | 알콘 인코포레이티드 | 실리콘 하이드로겔 콘택트 렌즈 상에 안정한 코팅을 적용하기 위한 방법 |
| US11331022B2 (en) | 2017-10-24 | 2022-05-17 | Dexcom, Inc. | Pre-connected analyte sensors |
| US11382540B2 (en) | 2017-10-24 | 2022-07-12 | Dexcom, Inc. | Pre-connected analyte sensors |
| CN117492228A (zh) | 2017-12-13 | 2024-02-02 | 爱尔康公司 | 周抛和月抛水梯度接触镜片 |
| KR102598533B1 (ko) * | 2018-08-24 | 2023-11-03 | 현대자동차주식회사 | 디-글루카로-1,4:6,3-다이락톤의 제조방법 |
| WO2021045203A1 (ja) * | 2019-09-05 | 2021-03-11 | 国立大学法人大阪大学 | 高分子材料及びその製造方法 |
| US20210162692A1 (en) * | 2019-12-02 | 2021-06-03 | Bausch & Lomb Ireland Limited | Direct compression molded ophthalmic devices |
| US20230100274A1 (en) * | 2020-02-25 | 2023-03-30 | Shiseido Company, Ltd. | Resin material including siloxane-bond-containing polymer having host group and/or guest group |
| WO2023003043A1 (ja) * | 2021-07-21 | 2023-01-26 | 国立大学法人大阪大学 | シリコーン系高分子化合物及びシリコーン系高分子材料 |
| CN118806984A (zh) * | 2023-04-17 | 2024-10-22 | 杭州启明医疗器械股份有限公司 | 可植入材料及其合成方法和人工心脏瓣膜 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3535283A1 (de) * | 1985-10-03 | 1987-04-09 | Byk Chemie Gmbh | Polyestergruppenhaltige polysiloxane fuer lacke und formmassen und die verwendung hierfuer |
| US4737558A (en) | 1985-11-25 | 1988-04-12 | Alcon Laboratories, Inc. | Siloxane copolymers for ophthalmic applications |
| US5221724A (en) * | 1987-08-12 | 1993-06-22 | Wisconsin Alumni Research Foundation | Polysiloxane polyurea urethanes |
| US4942212A (en) * | 1988-01-20 | 1990-07-17 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Polyurethane resin and heat-sensitive recording medium |
| US4983702A (en) | 1988-09-28 | 1991-01-08 | Ciba-Geigy Corporation | Crosslinked siloxane-urethane polymer contact lens |
| US4883854A (en) * | 1988-09-30 | 1989-11-28 | Medtronic, Inc. | Hydroxyl functional monomers |
| US4962178A (en) | 1988-11-03 | 1990-10-09 | Ciba-Geigy Corporation | Novel polysiloxane-polyurethanes and contact lens thereof |
| JPH02228323A (ja) | 1989-03-02 | 1990-09-11 | Dainichiseika Color & Chem Mfg Co Ltd | シロキサン変性ポリエステル系樹脂及びその製造方法 |
| US5196458A (en) * | 1991-10-15 | 1993-03-23 | Johnson & Johnson Vision Products, Inc. | Soft, high oxygen permeability ophthalmic lens |
| US5589563A (en) * | 1992-04-24 | 1996-12-31 | The Polymer Technology Group | Surface-modifying endgroups for biomedical polymers |
| DK0586332T3 (da) * | 1992-08-05 | 1997-04-14 | Max Planck Gesellschaft | Kontaktlinser af lipofiliserede cyclodextriner |
| DE4243799A1 (de) * | 1992-12-23 | 1994-06-30 | Bayer Ag | Siloxanblockcopolymer-modifizierte thermoplastische Polyurethane |
| EP0784641B1 (en) | 1994-10-04 | 2002-01-02 | Minnesota Mining And Manufacturing Company | Reactive two-part polyurethane compositions and optionally self-healable and scratch-resistant coatings prepared therefrom |
| US6039913A (en) * | 1998-08-27 | 2000-03-21 | Novartis Ag | Process for the manufacture of an ophthalmic molding |
-
1996
- 1996-12-10 AT AT96943907T patent/ATE223933T1/de not_active IP Right Cessation
- 1996-12-10 AU AU13693/97A patent/AU1369397A/en not_active Abandoned
- 1996-12-10 EP EP96943907A patent/EP0868457B1/en not_active Expired - Lifetime
- 1996-12-10 JP JP09523259A patent/JP2000506554A/ja not_active Ceased
- 1996-12-10 WO PCT/EP1996/005507 patent/WO1997023532A1/en not_active Ceased
- 1996-12-10 DE DE69623647T patent/DE69623647T2/de not_active Expired - Lifetime
- 1996-12-10 US US09/091,394 patent/US6271332B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2000506554A (ja) | 2000-05-30 |
| EP0868457B1 (en) | 2002-09-11 |
| US6271332B1 (en) | 2001-08-07 |
| ATE223933T1 (de) | 2002-09-15 |
| EP0868457A1 (en) | 1998-10-07 |
| DE69623647D1 (en) | 2002-10-17 |
| AU1369397A (en) | 1997-07-17 |
| WO1997023532A1 (en) | 1997-07-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8328 | Change in the person/name/address of the agent |
Representative=s name: PFENNING MEINIG & PARTNER GBR, 80339 MUENCHEN |
|
| 8364 | No opposition during term of opposition |