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)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Silicon Polymers (AREA)
- Polyethers (AREA)
- Polyurethanes Or Polyureas (AREA)
- Eyeglasses (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (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 (enExample) |
| EP (1) | EP1122258B1 (enExample) |
| JP (2) | JP5477832B2 (enExample) |
| AT (1) | ATE266668T1 (enExample) |
| AU (1) | AU2000275327A1 (enExample) |
| DE (1) | DE60010644T2 (enExample) |
| WO (1) | WO2001057047A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003062290A1 (en) | 2002-01-16 | 2003-07-31 | 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 |
| US7540609B2 (en) | 2006-06-15 | 2009-06-02 | 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 |
| EP2444448A1 (en) * | 2009-06-15 | 2012-04-25 | DSM IP Assets B.V. | Phosphorylcholine-based amphiphilic silicones for medical applications |
| WO2012086762A1 (ja) * | 2010-12-24 | 2012-06-28 | 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 |
| CN104066756A (zh) * | 2011-09-01 | 2014-09-24 | 弗特鲁斯专业公司 | 生产生物相容材料的方法 |
| ES2644132T3 (es) | 2011-09-01 | 2017-11-27 | Vertellus Holdings Llc | Material biocompatible |
| GB201119363D0 (en) * | 2011-11-10 | 2011-12-21 | Vertellus Specialities Inc | Polymerisable material |
| EP3193171B1 (en) * | 2014-09-10 | 2019-05-29 | NOF Corporation | Use of a protein adsorption inhibitor and method for inhibiting protein adsorption |
| 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 |
| CN113544176B (zh) | 2019-04-25 | 2023-04-25 | 日油株式会社 | 隐形眼镜用单体组合物、隐形眼镜用聚合物及其制备方法、以及隐形眼镜及其制造方法 |
| US20250122322A1 (en) * | 2021-07-30 | 2025-04-17 | Koei Chemical Company, Limited | Zwitterionic compound, and blocking agent dissociation catalyst for blocked isocyanate, blocked isocyanate composition containing blocking agent dissociation catalyst, thermosetting resin composition, cured product and method for manufacturing same, and carbonate compound |
| JPWO2023033013A1 (enExample) * | 2021-08-31 | 2023-03-09 | ||
| WO2023033012A1 (ja) * | 2021-08-31 | 2023-03-09 | 日油株式会社 | ホスホリルコリン基と水酸基を有するポリジメチルシロキサン含有モノマー |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3070993D1 (en) | 1979-12-20 | 1985-09-19 | 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 |
| ES2063478T3 (es) * | 1990-04-26 | 1995-01-01 | Ciba Geigy Ag | Polisiloxanos de urea insaturados. |
| 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 |
| CA2313676C (en) * | 1991-07-05 | 2006-10-10 | Biocompatibles Limited | Polymeric surface coatings |
| ATE196303T1 (de) * | 1991-08-08 | 2000-09-15 | Biocompatibles Ltd | Polymere oberflächenbeschichtungszusammensetzung |
| GB9118597D0 (en) | 1991-08-30 | 1991-10-16 | Biocompatibles Ltd | Polymer treatments |
| WO1993022320A1 (en) | 1992-04-24 | 1993-11-11 | Biocompatibles Limited | Metal coatings |
| GB9301702D0 (en) | 1993-01-28 | 1993-03-17 | Biocompatibles Ltd | New materials |
| GB9301701D0 (en) | 1993-01-28 | 1993-03-17 | Biocompatibles Ltd | New zwitterionic 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 |
| EP0913416B1 (en) * | 1997-04-17 | 2005-10-19 | Toyobo Co., Ltd. | Biocompatible polymers |
| DE19803468A1 (de) | 1998-01-29 | 1999-08-05 | Wacker Chemie Gmbh | Durch Michael-Addition-ähnliche Reaktionen vernetzte Aminosiliconölemulsionen |
| AU3383901A (en) * | 2000-02-07 | 2001-08-14 | Biocompatibles Limited | Silicon containing compounds |
| 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 DE DE60010644T patent/DE60010644T2/de not_active Expired - Lifetime
- 2000-02-07 EP EP00300943A patent/EP1122258B1/en not_active Expired - Lifetime
- 2000-02-07 AT AT00300943T patent/ATE266668T1/de not_active IP Right Cessation
- 2000-09-15 JP JP2001557878A patent/JP5477832B2/ja not_active Expired - Fee Related
- 2000-09-15 US US10/203,212 patent/US6828029B1/en not_active Expired - Lifetime
- 2000-09-15 AU AU2000275327A patent/AU2000275327A1/en not_active Abandoned
- 2000-09-15 WO PCT/GB2000/003557 patent/WO2001057047A1/en not_active Ceased
-
2010
- 2010-12-15 JP JP2010279729A patent/JP2011099106A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU2000275327A1 (en) | 2001-08-14 |
| DE60010644D1 (de) | 2004-06-17 |
| US6828029B1 (en) | 2004-12-07 |
| JP2011099106A (ja) | 2011-05-19 |
| ATE266668T1 (de) | 2004-05-15 |
| JP5477832B2 (ja) | 2014-04-23 |
| EP1122258A1 (en) | 2001-08-08 |
| WO2001057047A1 (en) | 2001-08-09 |
| EP1122258B1 (en) | 2004-05-12 |
| JP2004500458A (ja) | 2004-01-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60010644T2 (de) | Silizium enthaltende Verbindungen hergestellt durch Michael Addition als Monomere und Macromere | |
| DE69920484T2 (de) | Verfahren zur herstellung von beschichteten geformten polymeren gegenständen | |
| DE69415176T2 (de) | Diaminvorprodukte für blockcopolymere und verfahren zur herstellung solcher diamine | |
| 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 | |
| EP0543303B1 (de) | Hydrophile, hochquellfähige Hydrogele | |
| DE69722603T2 (de) | Verfahren zur herstellung von eines poröses polymer aus einer mischung | |
| 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 | |
| EP1469893A1 (de) | Sternformige prapolymere fur die herstellung ultradunner hydrogel-bildender beschichtungen | |
| DE60011124T2 (de) | Materialen aus polymermischungen auf basis von zwitterionischem polymer | |
| KR101539804B1 (ko) | 폴리실록산, 아크릴계 화합물 및 비닐계 화합물 | |
| US11572429B2 (en) | Hydrogels based on vinyl-caprolactam | |
| EP2134727B1 (de) | Methylolgruppen enthaltende siloxane | |
| EP2024408A1 (de) | Über methylolgruppen vernetzbare siliconpolymere | |
| DE602005004916T2 (de) | Neue präpolymere für verbesserte oberflächenveränderung von kontaktlinsen | |
| DE60102076T2 (de) | Reaktive polymere | |
| Yoo et al. | Characteristics of crosslinked blends of Pellethene® and multiblock polyurethanes containing phospholipid | |
| WO2010072541A1 (de) | Vernetzung von auf einem substrat vorliegender organopolysiloxanverbindung mit gasförmigem aldehydreagens | |
| DE10203937A1 (de) | Sternförmige Präpolymere für die Herstellung ultradünner, Hydrogel-bildender Beschichtungen | |
| DE10216639A1 (de) | Sternförmige Präpolymere für die Herstellung ultradünner, Hydrogelbildender Beschichtungen | |
| WO2010072531A1 (de) | Thermische vernetzung von auf einem substrat vorliegender organopolysiloxanverbindung mit aldehydreagens |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |