CA2859929A1 - Silicone hydrogels formed from zero diluent reactive mixtures - Google Patents
Silicone hydrogels formed from zero diluent reactive mixtures Download PDFInfo
- Publication number
- CA2859929A1 CA2859929A1 CA2859929A CA2859929A CA2859929A1 CA 2859929 A1 CA2859929 A1 CA 2859929A1 CA 2859929 A CA2859929 A CA 2859929A CA 2859929 A CA2859929 A CA 2859929A CA 2859929 A1 CA2859929 A1 CA 2859929A1
- Authority
- CA
- Canada
- Prior art keywords
- silicone hydrogel
- monomer
- methyl
- vinyl
- hydroxyl
- 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.)
- Abandoned
Links
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 138
- 239000000017 hydrogel Substances 0.000 title claims abstract description 98
- 239000000203 mixture Substances 0.000 title claims abstract description 83
- 239000003085 diluting agent Substances 0.000 title claims abstract description 27
- 239000000178 monomer Substances 0.000 claims abstract description 149
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 78
- 229920006294 polydialkylsiloxane Polymers 0.000 claims abstract description 19
- -1 trimethylsiloxy groups Chemical group 0.000 claims description 82
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 43
- 239000011541 reaction mixture Substances 0.000 claims description 43
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical group CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 40
- 229910001868 water Inorganic materials 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 34
- 239000004971 Cross linker Substances 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 229920002554 vinyl polymer Polymers 0.000 claims description 25
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 22
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 22
- 239000001301 oxygen Substances 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 12
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 claims description 12
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 12
- 229910052710 silicon Inorganic materials 0.000 claims description 12
- 229920001223 polyethylene glycol Polymers 0.000 claims description 11
- VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical group OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 claims description 10
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 10
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 9
- 125000001033 ether group Chemical group 0.000 claims description 9
- 239000010703 silicon Substances 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- 150000003926 acrylamides Chemical class 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000005504 styryl group Chemical group 0.000 claims description 6
- AFXKUUDFKHVAGI-UHFFFAOYSA-N 1-methyl-3-methylidenepyrrolidin-2-one Chemical compound CN1CCC(=C)C1=O AFXKUUDFKHVAGI-UHFFFAOYSA-N 0.000 claims description 5
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 claims description 5
- WULAHPYSGCVQHM-UHFFFAOYSA-N 2-(2-ethenoxyethoxy)ethanol Chemical compound OCCOCCOC=C WULAHPYSGCVQHM-UHFFFAOYSA-N 0.000 claims description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 230000004048 modification Effects 0.000 claims description 5
- 238000012986 modification Methods 0.000 claims description 5
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 5
- ONMLAAZEQUPQSE-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(C)CO ONMLAAZEQUPQSE-UHFFFAOYSA-N 0.000 claims description 4
- ZZDBHIVVDUTWJC-UHFFFAOYSA-N 1-methyl-5-methylidenepyrrolidin-2-one Chemical compound CN1C(=C)CCC1=O ZZDBHIVVDUTWJC-UHFFFAOYSA-N 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- VDORPYPVQAFLTR-UHFFFAOYSA-N 5-methyl-3-methylidenepyrrolidin-2-one Chemical compound CC1CC(=C)C(=O)N1 VDORPYPVQAFLTR-UHFFFAOYSA-N 0.000 claims description 4
- 239000006096 absorbing agent Substances 0.000 claims description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 claims description 2
- PBGPBHYPCGDFEZ-UHFFFAOYSA-N 1-ethenylpiperidin-2-one Chemical compound C=CN1CCCCC1=O PBGPBHYPCGDFEZ-UHFFFAOYSA-N 0.000 claims description 2
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims description 2
- IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 claims description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 claims description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 2
- XVUWMCJNMDQXKX-UHFFFAOYSA-N 5-ethyl-3-methylidenepyrrolidin-2-one Chemical compound CCC1CC(=C)C(=O)N1 XVUWMCJNMDQXKX-UHFFFAOYSA-N 0.000 claims description 2
- 125000006519 CCH3 Chemical group 0.000 claims description 2
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 2
- GORGQKRVQGXVEB-UHFFFAOYSA-N n-ethenyl-n-ethylacetamide Chemical compound CCN(C=C)C(C)=O GORGQKRVQGXVEB-UHFFFAOYSA-N 0.000 claims description 2
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims description 2
- KYKIFKUTBWKKRE-UHFFFAOYSA-N n-ethenylpropan-2-amine Chemical compound CC(C)NC=C KYKIFKUTBWKKRE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- CXNYYQBHNJHBNH-UHFFFAOYSA-N 1-ethyl-5-methylidenepyrrolidin-2-one Chemical compound CCN1C(=C)CCC1=O CXNYYQBHNJHBNH-UHFFFAOYSA-N 0.000 claims 1
- ACOUENYDWAONBH-UHFFFAOYSA-N 3-methylidene-1-propan-2-ylpyrrolidin-2-one Chemical compound CC(C)N1CCC(=C)C1=O ACOUENYDWAONBH-UHFFFAOYSA-N 0.000 claims 1
- XVGZUJYMDCFKIZ-UHFFFAOYSA-N 3-methylidene-1-propylpyrrolidin-2-one Chemical compound CCCN1CCC(=C)C1=O XVGZUJYMDCFKIZ-UHFFFAOYSA-N 0.000 claims 1
- YNQNQJPLBDEVRW-UHFFFAOYSA-N 5-methylidene-1-propan-2-ylpyrrolidin-2-one Chemical compound CC(C)N1C(=C)CCC1=O YNQNQJPLBDEVRW-UHFFFAOYSA-N 0.000 claims 1
- RRUNPGIXAGEPSW-UHFFFAOYSA-N 5-methylidene-1-propylpyrrolidin-2-one Chemical compound CCCN1C(=C)CCC1=O RRUNPGIXAGEPSW-UHFFFAOYSA-N 0.000 claims 1
- FXPHJTKVWZVEGA-UHFFFAOYSA-N ethenyl hydrogen carbonate Chemical class OC(=O)OC=C FXPHJTKVWZVEGA-UHFFFAOYSA-N 0.000 claims 1
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical class NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 0.000 claims 1
- 229920001567 vinyl ester resin Polymers 0.000 claims 1
- 239000000243 solution Substances 0.000 description 51
- 238000000034 method Methods 0.000 description 35
- 102100026735 Coagulation factor VIII Human genes 0.000 description 33
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 33
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 23
- 239000002953 phosphate buffered saline Substances 0.000 description 23
- 238000009472 formulation Methods 0.000 description 21
- 229920000642 polymer Polymers 0.000 description 20
- 239000000523 sample Substances 0.000 description 19
- 102000016943 Muramidase Human genes 0.000 description 18
- 108010014251 Muramidase Proteins 0.000 description 18
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 18
- 235000010335 lysozyme Nutrition 0.000 description 18
- 239000004325 lysozyme Substances 0.000 description 18
- 229960000274 lysozyme Drugs 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 230000003287 optical effect Effects 0.000 description 14
- 102000019298 Lipocalin Human genes 0.000 description 13
- 108050006654 Lipocalin Proteins 0.000 description 13
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 12
- 230000035699 permeability Effects 0.000 description 12
- 102000015728 Mucins Human genes 0.000 description 11
- 108010063954 Mucins Proteins 0.000 description 11
- 239000000284 extract Substances 0.000 description 10
- 238000012856 packing Methods 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000003247 decreasing effect Effects 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 239000003431 cross linking reagent Substances 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 125000005376 alkyl siloxane group Chemical group 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 238000004364 calculation method Methods 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 4
- 230000036571 hydration Effects 0.000 description 4
- 238000006703 hydration reaction Methods 0.000 description 4
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 229920001169 thermoplastic Polymers 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 3
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-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
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- AFYNADDZULBEJA-UHFFFAOYSA-N bicinchoninic acid Chemical compound C1=CC=CC2=NC(C=3C=C(C4=CC=CC=C4N=3)C(=O)O)=CC(C(O)=O)=C21 AFYNADDZULBEJA-UHFFFAOYSA-N 0.000 description 3
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 3
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- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 3
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- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 2
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- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 2
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- 125000000129 anionic group Chemical group 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
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- 229910021641 deionized water Inorganic materials 0.000 description 2
- 125000005594 diketone group Chemical group 0.000 description 2
- 125000001303 disiloxanyl group Chemical group [H][Si]([*])([H])O[Si]([H])([H])[H] 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
- C08F283/124—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes on to polysiloxanes having carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/068—Polysiloxanes
-
- 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
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/442—Block-or graft-polymers containing polysiloxane sequences containing vinyl polymer sequences
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- G—PHYSICS
- G02—OPTICS
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- 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
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Landscapes
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- Macromonomer-Based Addition Polymer (AREA)
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- Silicon Polymers (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (7)
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2012
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- 2012-12-20 RU RU2014130241A patent/RU2629932C2/ru active
- 2012-12-20 KR KR1020147020570A patent/KR102048679B1/ko active Active
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| SG11201403467UA (en) | 2014-09-26 |
| HK1203536A1 (en) | 2015-10-30 |
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| US10017596B2 (en) | 2018-07-10 |
| KR102048679B1 (ko) | 2019-11-27 |
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| TW201341417A (zh) | 2013-10-16 |
| BR112014015438A8 (pt) | 2017-07-04 |
| JP2017165987A (ja) | 2017-09-21 |
| CN104144971A (zh) | 2014-11-12 |
| EP3473662A1 (en) | 2019-04-24 |
| US20170129983A1 (en) | 2017-05-11 |
| JP6348209B2 (ja) | 2018-06-27 |
| JP6169604B2 (ja) | 2017-07-26 |
| CN104144971B (zh) | 2017-03-15 |
| EP2794724B1 (en) | 2018-07-18 |
| EP2794724B9 (en) | 2019-01-09 |
| TWI582122B (zh) | 2017-05-11 |
| KR20140106735A (ko) | 2014-09-03 |
| JP2015504108A (ja) | 2015-02-05 |
| US9588258B2 (en) | 2017-03-07 |
| WO2013096594A8 (en) | 2014-07-17 |
| WO2013096594A1 (en) | 2013-06-27 |
| RU2629932C2 (ru) | 2017-09-05 |
| RU2014130241A (ru) | 2016-02-20 |
| EP2794724A1 (en) | 2014-10-29 |
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