DE60010644T2 - Silizium enthaltende Verbindungen hergestellt durch Michael Addition als Monomere und Macromere - Google Patents
Silizium enthaltende Verbindungen hergestellt durch Michael Addition als Monomere und Macromere Download PDFInfo
- Publication number
- DE60010644T2 DE60010644T2 DE60010644T DE60010644T DE60010644T2 DE 60010644 T2 DE60010644 T2 DE 60010644T2 DE 60010644 T DE60010644 T DE 60010644T DE 60010644 T DE60010644 T DE 60010644T DE 60010644 T2 DE60010644 T2 DE 60010644T2
- Authority
- DE
- Germany
- Prior art keywords
- group
- groups
- aryl
- hydrogen
- alkyl
- 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
- 238000006845 Michael addition reaction Methods 0.000 title claims description 10
- 239000000178 monomer Substances 0.000 title claims description 7
- 239000002210 silicon-based material Substances 0.000 title 1
- -1 cycloalkynyl Chemical group 0.000 claims abstract description 53
- 239000001257 hydrogen Substances 0.000 claims abstract description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 52
- 229920000642 polymer Polymers 0.000 claims abstract description 43
- 125000003118 aryl group Chemical group 0.000 claims abstract description 36
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 34
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 21
- 125000005375 organosiloxane group Chemical group 0.000 claims abstract description 21
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 20
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 17
- 150000001282 organosilanes Chemical class 0.000 claims abstract description 16
- 238000000576 coating method Methods 0.000 claims abstract description 15
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims abstract description 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 10
- 125000004171 alkoxy aryl group Chemical group 0.000 claims abstract description 10
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 10
- 125000005128 aryl amino alkyl group Chemical group 0.000 claims abstract description 10
- 230000008569 process Effects 0.000 claims abstract description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 9
- 125000003106 haloaryl group Chemical group 0.000 claims abstract description 9
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims abstract description 9
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims abstract description 8
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 7
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 5
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 5
- 150000004714 phosphonium salts Chemical class 0.000 claims abstract description 5
- 125000001174 sulfone group Chemical group 0.000 claims abstract description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 60
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 23
- 239000012948 isocyanate Substances 0.000 claims description 18
- 150000002513 isocyanates Chemical group 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000005442 diisocyanate group Chemical group 0.000 claims description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
- 125000002091 cationic group Chemical group 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 10
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 9
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 7
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 claims description 7
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000000129 anionic group Chemical group 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- ZVEMLYIXBCTVOF-UHFFFAOYSA-N 1-(2-isocyanatopropan-2-yl)-3-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC(C(C)(C)N=C=O)=C1 ZVEMLYIXBCTVOF-UHFFFAOYSA-N 0.000 claims description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 5
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 229910003849 O-Si Inorganic materials 0.000 claims description 4
- 229910003872 O—Si Inorganic materials 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 3
- 238000007334 copolymerization reaction Methods 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 238000010526 radical polymerization reaction Methods 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005001 aminoaryl group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 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 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 150000003512 tertiary amines Chemical group 0.000 claims description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 2
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 abstract 1
- 125000005133 alkynyloxy group Chemical group 0.000 abstract 1
- 125000002431 aminoalkoxy group Chemical group 0.000 abstract 1
- 125000004465 cycloalkenyloxy group Chemical group 0.000 abstract 1
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 abstract 1
- 125000002560 nitrile group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 24
- 241000219739 Lens Species 0.000 description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- 239000000463 material Substances 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 239000004205 dimethyl polysiloxane Substances 0.000 description 9
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 229920003226 polyurethane urea Polymers 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 0 CCCC*C(C)=C(C)[C@](CC(C)(C)*)C(*)C(CCC1CC(C2)C2=CCCCC)C1=C Chemical compound CCCC*C(C)=C(C)[C@](CC(C)(C)*)C(*)C(CCC1CC(C2)C2=CCCCC)C1=C 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 102000004169 proteins and genes Human genes 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 229940012952 fibrinogen Drugs 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000001179 sorption measurement Methods 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- 102000008946 Fibrinogen Human genes 0.000 description 4
- 108010049003 Fibrinogen Proteins 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 235000013877 carbamide Nutrition 0.000 description 4
- 230000035699 permeability Effects 0.000 description 4
- 150000003904 phospholipids Chemical class 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 240000001414 Eucalyptus viminalis Species 0.000 description 3
- 235000014647 Lens culinaris subsp culinaris Nutrition 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 3
- 125000003158 alcohol group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000017 hydrogel Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000013557 residual solvent Substances 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 239000004970 Chain extender Substances 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000000944 Soxhlet extraction Methods 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 238000012925 biological evaluation Methods 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 238000003018 immunoassay Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 description 1
- SBMUNILHNJLMBF-UHFFFAOYSA-N 2-chloro-1,3,2$l^{5}-dioxaphospholane 2-oxide Chemical compound ClP1(=O)OCCO1 SBMUNILHNJLMBF-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BCAIDFOKQCVACE-UHFFFAOYSA-N 3-[dimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azaniumyl]propane-1-sulfonate Chemical compound CC(=C)C(=O)OCC[N+](C)(C)CCCS([O-])(=O)=O BCAIDFOKQCVACE-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- QUNAGQLGMPHBQM-UHFFFAOYSA-O C[N+](C)(C)CC(O)=P(=O)C(=O)C=C Chemical compound C[N+](C)(C)CC(O)=P(=O)C(=O)C=C QUNAGQLGMPHBQM-UHFFFAOYSA-O 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 244000025272 Persea americana Species 0.000 description 1
- 235000008673 Persea americana Nutrition 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000005100 aryl amino carbonyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000013060 biological fluid Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 239000003618 borate buffered saline Substances 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000005935 nucleophilic addition reaction Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- OTYBJBJYBGWBHB-UHFFFAOYSA-N trimethylsilyl prop-2-enoate Chemical class C[Si](C)(C)OC(=O)C=C OTYBJBJYBGWBHB-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/395—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing phosphorus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Polyethers (AREA)
- Silicon Polymers (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Polyurethanes Or Polyureas (AREA)
- Eyeglasses (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00300943A EP1122258B1 (en) | 2000-02-07 | 2000-02-07 | Silicon containing compounds from Michael-type adduct reactions useful as monomers and macromers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60010644D1 DE60010644D1 (de) | 2004-06-17 |
| DE60010644T2 true DE60010644T2 (de) | 2005-05-19 |
Family
ID=8172686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60010644T Expired - Lifetime DE60010644T2 (de) | 2000-02-07 | 2000-02-07 | Silizium enthaltende Verbindungen hergestellt durch Michael Addition als Monomere und Macromere |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6828029B1 (cg-RX-API-DMAC10.html) |
| EP (1) | EP1122258B1 (cg-RX-API-DMAC10.html) |
| JP (2) | JP5477832B2 (cg-RX-API-DMAC10.html) |
| AT (1) | ATE266668T1 (cg-RX-API-DMAC10.html) |
| AU (1) | AU2000275327A1 (cg-RX-API-DMAC10.html) |
| DE (1) | DE60010644T2 (cg-RX-API-DMAC10.html) |
| WO (1) | WO2001057047A1 (cg-RX-API-DMAC10.html) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8048408B2 (en) * | 2002-01-16 | 2011-11-01 | Biocompatibles Uk Limited | Polymer conjugates |
| JP3707780B2 (ja) | 2002-06-24 | 2005-10-19 | 東京応化工業株式会社 | パターン微細化用被覆形成剤およびそれを用いた微細パターンの形成方法 |
| JP4245336B2 (ja) * | 2002-11-25 | 2009-03-25 | 株式会社資生堂 | ホスホリルコリン基を有するポリシロキサン及びその製造方法 |
| GB0301014D0 (en) * | 2003-01-16 | 2003-02-19 | Biocompatibles Ltd | Conjugation reactions |
| JP4730886B2 (ja) * | 2005-06-01 | 2011-07-20 | 信越化学工業株式会社 | 紫外線吸収性基含有オルガノポリシロキサン、該ポリシロキサンの製造方法、及び該ポリシロキサンを配合してなる処理剤 |
| US8231218B2 (en) | 2006-06-15 | 2012-07-31 | Coopervision International Holding Company, Lp | Wettable silicone hydrogel contact lenses and related compositions and methods |
| US7572841B2 (en) | 2006-06-15 | 2009-08-11 | Coopervision International Holding Company, Lp | Wettable silicone hydrogel contact lenses and related compositions and methods |
| US7540609B2 (en) | 2006-06-15 | 2009-06-02 | Coopervision International Holding Company, Lp | Wettable silicone hydrogel contact lenses and related compositions and methods |
| EP2444448A1 (en) * | 2009-06-15 | 2012-04-25 | DSM IP Assets B.V. | Phosphorylcholine-based amphiphilic silicones for medical applications |
| JP5846125B2 (ja) * | 2010-12-24 | 2016-01-20 | 日油株式会社 | アミノ基含有ホスホリルコリン化合物及びその製造方法 |
| SG11201400287XA (en) * | 2011-09-01 | 2014-03-28 | Vertellus Specialties Inc | Methods for producing biocompatible materials |
| US9006305B2 (en) | 2011-09-01 | 2015-04-14 | Vertellus Specialties Inc. | Biocompatible material |
| GB201119363D0 (en) | 2011-11-10 | 2011-12-21 | Vertellus Specialities Inc | Polymerisable material |
| WO2016039319A1 (ja) * | 2014-09-10 | 2016-03-17 | 日油株式会社 | 蛋白質吸着抑制剤及び蛋白質吸着抑制方法 |
| WO2016123806A1 (zh) | 2015-02-06 | 2016-08-11 | 深圳大学 | 一种反应性抗菌防污化合物及其制备方法 |
| JP7087552B2 (ja) * | 2018-03-29 | 2022-06-21 | 東洋インキＳｃホールディングス株式会社 | コーティング用組成物および塗膜 |
| TWI813663B (zh) | 2018-04-05 | 2023-09-01 | 日商日油股份有限公司 | 含磷醯膽鹼基的聚矽氧烷單體 |
| SG11202111751QA (en) | 2019-04-25 | 2021-11-29 | Nof Corp | Monomer composition for contact lenses, polymer for contact lenses and method for producing same, and contact lens and method for producing same |
| CN117769574A (zh) * | 2021-07-30 | 2024-03-26 | 广荣化学株式会社 | 两性离子化合物、封端异氰酸酯的封端剂解离催化剂及含其的封端异氰酸酯组合物、热固树脂组合物、固化物及制备方法、碳酸酯化合物 |
| EP4397694A4 (en) * | 2021-08-31 | 2025-11-19 | Nof Corp | MONOMER CONTAINING POLYDIMETHYLSILOXANE HAVING A PHOSPHORYLCHOLINE GROUP AND A HYDROXYL GROUP |
| KR20240051140A (ko) * | 2021-08-31 | 2024-04-19 | 니치유 가부시키가이샤 | 포스포릴콜린기와 수산기를 갖는 폴리디메틸실록산 함유 모노머 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0032622B1 (en) | 1979-12-20 | 1985-08-14 | Dennis Chapman | Polymerisable phospholipids and polymers thereof, methods for their preparation, methods for their use in coating substrates and forming liposomes and the resulting coated substrates and liposome compositions |
| US4507466A (en) | 1983-01-07 | 1985-03-26 | The Dow Chemical Corporation | Dense star polymers having core, core branches, terminal groups |
| US5380904A (en) | 1984-01-20 | 1995-01-10 | Biocompatibles Ltd. | Process for rendering a surface biocompatible, and articles containing the same |
| JPH0618866B2 (ja) | 1986-12-22 | 1994-03-16 | 鐘淵化学工業株式会社 | 常温硬化性樹脂の製造法 |
| US5073578A (en) | 1990-02-23 | 1991-12-17 | Unilever Patent Holdings B.V. | Core-shell copolymer emulsions for flexible coatings |
| GB9004881D0 (en) * | 1990-03-05 | 1990-05-02 | Biocompatibles Ltd | Method of improving the ocular of synthetic polymers haemo and biocompatibility |
| DE69101464T2 (de) * | 1990-04-26 | 1994-07-14 | Ciba Geigy | Ungesättigte Harnstoff-Polysiloxane. |
| JPH04119174A (ja) * | 1990-09-10 | 1992-04-20 | Toray Dow Corning Silicone Co Ltd | 繊維処理剤 |
| GB9023498D0 (en) | 1990-10-29 | 1990-12-12 | Biocompatibles Ltd | Soft contact lens material |
| AU666485B2 (en) * | 1991-07-05 | 1996-02-15 | Biocompatibles Uk Limited | Polymeric surface coatings |
| ATE270310T1 (de) * | 1991-08-08 | 2004-07-15 | Biocompatibles Uk Ltd | Polymere oberflächenbeschichtungszusammensetzungen |
| GB9118597D0 (en) | 1991-08-30 | 1991-10-16 | Biocompatibles Ltd | Polymer treatments |
| JPH07505900A (ja) | 1992-04-24 | 1995-06-29 | バイオコンパテイブルズ・リミテツド | 金属皮膜 |
| GB9301701D0 (en) | 1993-01-28 | 1993-03-17 | Biocompatibles Ltd | New zwitterionic materials |
| GB9301702D0 (en) | 1993-01-28 | 1993-03-17 | Biocompatibles Ltd | New materials |
| US5792827A (en) | 1994-01-13 | 1998-08-11 | Basf Lacke + Farben, Ag | Addition products, radiation-curable surface coating compositions based on the addition products and their use for woodcoating and papercoating |
| US6194539B1 (en) | 1994-11-22 | 2001-02-27 | Daicel Chemical Industries, Inc. | Polylactone having amino groups, a process for the preparation thereof, a compound having amino group, a composition for coatings, a composition for printing inks |
| US5739192A (en) * | 1996-11-20 | 1998-04-14 | Dow Corning Corporation | Polysiloxane copolymers from Michael Adduct reactions |
| US6040415A (en) * | 1997-04-17 | 2000-03-21 | Toyobo Co., Ltd. | Biocompatible polymers |
| DE19803468A1 (de) * | 1998-01-29 | 1999-08-05 | Wacker Chemie Gmbh | Durch Michael-Addition-ähnliche Reaktionen vernetzte Aminosiliconölemulsionen |
| JP2003522227A (ja) * | 2000-02-07 | 2003-07-22 | バイオコンパティブルズ リミテッド | シリコン含有化合物 |
| JP3715310B1 (ja) * | 2004-05-24 | 2005-11-09 | 株式会社資生堂 | 蛋白質吸着防止眼用レンズ材料及びその製造方法 |
-
2000
- 2000-02-07 AT AT00300943T patent/ATE266668T1/de not_active IP Right Cessation
- 2000-02-07 DE DE60010644T patent/DE60010644T2/de not_active Expired - Lifetime
- 2000-02-07 EP EP00300943A patent/EP1122258B1/en not_active Expired - Lifetime
- 2000-09-15 WO PCT/GB2000/003557 patent/WO2001057047A1/en not_active Ceased
- 2000-09-15 AU AU2000275327A patent/AU2000275327A1/en not_active Abandoned
- 2000-09-15 US US10/203,212 patent/US6828029B1/en not_active Expired - Lifetime
- 2000-09-15 JP JP2001557878A patent/JP5477832B2/ja not_active Expired - Fee Related
-
2010
- 2010-12-15 JP JP2010279729A patent/JP2011099106A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001057047A1 (en) | 2001-08-09 |
| DE60010644D1 (de) | 2004-06-17 |
| ATE266668T1 (de) | 2004-05-15 |
| AU2000275327A1 (en) | 2001-08-14 |
| JP2004500458A (ja) | 2004-01-08 |
| US6828029B1 (en) | 2004-12-07 |
| JP2011099106A (ja) | 2011-05-19 |
| EP1122258A1 (en) | 2001-08-08 |
| EP1122258B1 (en) | 2004-05-12 |
| JP5477832B2 (ja) | 2014-04-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69920484T2 (de) | Verfahren zur herstellung von beschichteten geformten polymeren gegenständen | |
| DE69415176T2 (de) | Diaminvorprodukte für blockcopolymere und verfahren zur herstellung solcher diamine | |
| DE60103621T2 (de) | Vernetzbare oder polymerisierbare präpolymere | |
| DE69021282T2 (de) | Prepolymere zur Verwendung in biomedizinischen Vorrichtungen. | |
| KR100422852B1 (ko) | 폴리디알킬실록산-폴리아미드 공중합체, 그 제조방법 및각종 재료 | |
| DE3034505C2 (de) | Kontaktlinse aus einem vernetzten, Polysiloxan und Acrylsäure- oder Methacrylsäureester enthaltenden Copolymerisat | |
| DE69722603T2 (de) | Verfahren zur herstellung von eines poröses polymer aus einer mischung | |
| DE69706852T2 (de) | Copolymere mit amphiphilen segmenten und kontrollierter morphologie; opthalmische produkte und kontaktlinsen auf basis diesen copolymeren | |
| EP1255761B1 (en) | Silicon containing compounds from michael - type addition reactions useful as monomers and macromers | |
| DE69319725T2 (de) | Polysiloxane, verfahren zur herstellung und polysiloxane mit hohem brechungsindex | |
| DE69935457T2 (de) | Perfluoroalkylpolyetherpolymere für ophthalmische anwendungen | |
| EP0793541B1 (de) | Nco-terminale vinyltelomere | |
| DE69839054T2 (de) | Biomimetrische materialien vom hydrogel-typ | |
| EP1122258B1 (en) | Silicon containing compounds from Michael-type adduct reactions useful as monomers and macromers | |
| DE4138408A1 (de) | Hydrophile, hochquellfaehige hydrogele | |
| DE2831274A1 (de) | Polysiloxanhydrogele | |
| EP1469893A1 (de) | Sternformige prapolymere fur die herstellung ultradunner hydrogel-bildender beschichtungen | |
| KR101539804B1 (ko) | 폴리실록산, 아크릴계 화합물 및 비닐계 화합물 | |
| US11572429B2 (en) | Hydrogels based on vinyl-caprolactam | |
| Dai et al. | Fabrication of reversible bacteria-killing and bacteria-releasing cotton fabrics with anti-bacteria adhesion capacity for potential application in reusable medical materials | |
| DE69233378T2 (de) | Polymere Oberflächenbeschichtungszusammensetzungen | |
| EP2134727B1 (de) | Methylolgruppen enthaltende siloxane | |
| WO2007131985A1 (de) | Über methylolgruppen vernetzbare siliconpolymere | |
| DE602005004916T2 (de) | Neue präpolymere für verbesserte oberflächenveränderung von kontaktlinsen | |
| DE60102076T2 (de) | Reaktive polymere |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |