SK4102001A3 - Photocurable siloxane polymers - Google Patents

Photocurable siloxane polymers Download PDF

Info

Publication number: SK4102001A3
Authority: SK; Slovakia
Prior art keywords: copolymer; photoinitiator; lenses; alkyl; polysiloxane
Prior art date: 1998-10-13

Application number

SK410-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Kenneth A Hodd

Sverker Norrby

Original Assignee

Pharmacia Groningen Bv

Priority date (The priority date 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 date listed.)

1998-10-13

Filing date

1999-10-11

Publication date

2001-11-06

1999-10-11 Application filed by Pharmacia Groningen Bv filed Critical Pharmacia Groningen Bv

2001-11-06 Publication of SK4102001A3 publication Critical patent/SK4102001A3/sk

Links

KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 title claims abstract description 39
229920000642 polymer Polymers 0.000 title abstract description 23
-1 acryl groups Chemical group 0.000 claims abstract description 111
229920001577 copolymer Polymers 0.000 claims abstract description 35
238000000034 method Methods 0.000 claims abstract description 28
229920001296 polysiloxane Polymers 0.000 claims description 74
239000000203 mixture Substances 0.000 claims description 38
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 37
239000000463 material Substances 0.000 claims description 21
229920001971 elastomer Polymers 0.000 claims description 20
239000000806 elastomer Substances 0.000 claims description 20
229920001897 terpolymer Polymers 0.000 claims description 20
239000000178 monomer Substances 0.000 claims description 18
239000004305 biphenyl Substances 0.000 claims description 13
239000003431 cross linking reagent Substances 0.000 claims description 12
230000008569 process Effects 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
230000005484 gravity Effects 0.000 claims description 9
235000010290 biphenyl Nutrition 0.000 claims description 8
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
125000006267 biphenyl group Chemical group 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
230000004308 accommodation Effects 0.000 claims description 5
125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
230000003287 optical effect Effects 0.000 claims description 5
238000007906 compression Methods 0.000 claims description 4
230000006835 compression Effects 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 3
238000011049 filling Methods 0.000 claims description 3
238000002156 mixing Methods 0.000 claims description 3
239000007787 solid Substances 0.000 claims description 3
230000000977 initiatory effect Effects 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims 1
230000000379 polymerizing effect Effects 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 19
NYMPGSQKHIOWIO-UHFFFAOYSA-N hydroxy(diphenyl)silicon Chemical compound C=1C=CC=CC=1[Si](O)C1=CC=CC=C1 NYMPGSQKHIOWIO-UHFFFAOYSA-N 0.000 abstract description 9
238000001727 in vivo Methods 0.000 abstract description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 12
239000007788 liquid Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
239000004205 dimethyl polysiloxane Substances 0.000 description 8
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 8
239000000047 product Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
238000004458 analytical method Methods 0.000 description 7
239000002775 capsule Substances 0.000 description 7
238000002347 injection Methods 0.000 description 7
239000007924 injection Substances 0.000 description 7
VSIKJPJINIDELZ-UHFFFAOYSA-N 2,2,4,4,6,6,8,8-octakis-phenyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound O1[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si]1(C=1C=CC=CC=1)C1=CC=CC=C1 VSIKJPJINIDELZ-UHFFFAOYSA-N 0.000 description 6
101100063974 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) dph-3 gene Proteins 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000001723 curing Methods 0.000 description 6
HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
238000004132 cross linking Methods 0.000 description 5
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 5
238000006116 polymerization reaction Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000000725 suspension Substances 0.000 description 4
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 4
URZHQOCYXDNFGN-UHFFFAOYSA-N 2,4,6-trimethyl-2,4,6-tris(3,3,3-trifluoropropyl)-1,3,5,2,4,6-trioxatrisilinane Chemical compound FC(F)(F)CC[Si]1(C)O[Si](C)(CCC(F)(F)F)O[Si](C)(CCC(F)(F)F)O1 URZHQOCYXDNFGN-UHFFFAOYSA-N 0.000 description 3
FGZFESWHQXSPJU-UHFFFAOYSA-N 2-methyl-2-(3,3,3-trifluoropropyl)-1,3,5,2,4,6-trioxatrisilinane Chemical compound FC(F)(F)CC[Si]1(C)O[SiH2]O[SiH2]O1 FGZFESWHQXSPJU-UHFFFAOYSA-N 0.000 description 3
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
101001047746 Homo sapiens Lamina-associated polypeptide 2, isoform alpha Proteins 0.000 description 3
101001047731 Homo sapiens Lamina-associated polypeptide 2, isoforms beta/gamma Proteins 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
102100023981 Lamina-associated polypeptide 2, isoform alpha Human genes 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000002350 accommodative effect Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
238000001879 gelation Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 description 3
PQPVPZTVJLXQAS-UHFFFAOYSA-N hydroxy-methyl-phenylsilicon Chemical class C[Si](O)C1=CC=CC=C1 PQPVPZTVJLXQAS-UHFFFAOYSA-N 0.000 description 3
239000003999 initiator Substances 0.000 description 3
238000007493 shaping process Methods 0.000 description 3
238000007711 solidification Methods 0.000 description 3
230000008023 solidification Effects 0.000 description 3
238000001356 surgical procedure Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
229920001187 thermosetting polymer Polymers 0.000 description 3
238000005406 washing Methods 0.000 description 3
ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 2
VCYDUTCMKSROID-UHFFFAOYSA-N 2,2,4,4,6,6-hexakis-phenyl-1,3,5,2,4,6-trioxatrisilinane Chemical compound O1[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si]1(C=1C=CC=CC=1)C1=CC=CC=C1 VCYDUTCMKSROID-UHFFFAOYSA-N 0.000 description 2
GPXCORHXFPYJEH-UHFFFAOYSA-N 3-[[3-aminopropyl(dimethyl)silyl]oxy-dimethylsilyl]propan-1-amine Chemical compound NCCC[Si](C)(C)O[Si](C)(C)CCCN GPXCORHXFPYJEH-UHFFFAOYSA-N 0.000 description 2
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
208000002177 Cataract Diseases 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
102100033617 Retinal-specific phospholipid-transporting ATPase ABCA4 Human genes 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
241000282887 Suidae Species 0.000 description 2
VVFMKHRTYGDEPI-UHFFFAOYSA-N [Ti]C1=CC=CC=C1 Chemical compound [Ti]C1=CC=CC=C1 VVFMKHRTYGDEPI-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
238000013459 approach Methods 0.000 description 2
230000008901 benefit Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
238000013461 design Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000000499 gel Substances 0.000 description 2
238000002513 implantation Methods 0.000 description 2
229920002521 macromolecule Polymers 0.000 description 2
238000005259 measurement Methods 0.000 description 2
VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
239000004926 polymethyl methacrylate Substances 0.000 description 2
IALUUOKJPBOFJL-UHFFFAOYSA-N potassium oxidosilane Chemical compound [K+].[SiH3][O-] IALUUOKJPBOFJL-UHFFFAOYSA-N 0.000 description 2
239000002243 precursor Substances 0.000 description 2
238000000518 rheometry Methods 0.000 description 2
229920005573 silicon-containing polymer Polymers 0.000 description 2
229920002545 silicone oil Polymers 0.000 description 2
229920002379 silicone rubber Polymers 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
YOIAWAIKYVEKMF-UHFFFAOYSA-N trifluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)F.OS(=O)(=O)C(F)(F)F YOIAWAIKYVEKMF-UHFFFAOYSA-N 0.000 description 2
125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
UTHDGOQKIWLLCO-UHFFFAOYSA-N 1-hydroxyhexyl prop-2-enoate Chemical compound CCCCCC(O)OC(=O)C=C UTHDGOQKIWLLCO-UHFFFAOYSA-N 0.000 description 1
UWKQJZCTQGMHKD-UHFFFAOYSA-N 2,6-di-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=N1 UWKQJZCTQGMHKD-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
BLKLMVJSMVIVOX-UHFFFAOYSA-N 3-[3-aminopropyl(dimethyl)silyl]oxysilylpropan-1-amine Chemical compound C[Si](C)(CCCN)O[SiH2]CCCN BLKLMVJSMVIVOX-UHFFFAOYSA-N 0.000 description 1
IOSZAJFVMXYBPJ-UHFFFAOYSA-N 6-[[6-hydroxyhexyl(dimethyl)silyl]oxy-dimethylsilyl]hexan-1-ol Chemical compound OCCCCCC[Si](C)(C)O[Si](C)(C)CCCCCCO IOSZAJFVMXYBPJ-UHFFFAOYSA-N 0.000 description 1
SXNICUVVDOTUPD-UHFFFAOYSA-N CC1=CC(C)=CC(C)=C1C(=O)P(=O)C1=CC=CC=C1 Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)C1=CC=CC=C1 SXNICUVVDOTUPD-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
101100278356 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) dph-4 gene Proteins 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
208000002847 Surgical Wound Diseases 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
MMWHKIZPIXENRV-UHFFFAOYSA-N [dimethyl(prop-2-enoyloxy)silyl]methyl prop-2-enoate Chemical compound C=CC(=O)O[Si](C)(C)COC(=O)C=C MMWHKIZPIXENRV-UHFFFAOYSA-N 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000003926 acrylamides Chemical class 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000036760 body temperature Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
210000004087 cornea Anatomy 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000007547 defect Effects 0.000 description 1
230000002950 deficient Effects 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
239000012975 dibutyltin dilaurate Substances 0.000 description 1
VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
230000006870 function Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000007943 implant Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000007972 injectable composition Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
230000001678 irradiating effect Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
125000005395 methacrylic acid group Chemical group 0.000 description 1
UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000000465 moulding Methods 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
238000000016 photochemical curing Methods 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
238000003825 pressing Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
150000004819 silanols Chemical class 0.000 description 1
229940024463 silicone emollient and protective product Drugs 0.000 description 1
239000004945 silicone rubber Substances 0.000 description 1
125000006850 spacer group Chemical group 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
125000004950 trifluoroalkyl group Chemical group 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G77/44—Block-or graft-polymers containing polysiloxane sequences containing only polysiloxane sequences
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- 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
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
- 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
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
- 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
- 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
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/06—Flowable or injectable implant compositions
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2430/00—Materials or treatment for tissue regeneration
- A61L2430/16—Materials or treatment for tissue regeneration for reconstruction of eye parts, e.g. intraocular lens, cornea
- 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
- C08G77/70—Siloxanes defined by use of the MDTQ nomenclature

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Physics & Mathematics (AREA)
General Physics & Mathematics (AREA)
Optics & Photonics (AREA)
Epidemiology (AREA)
Public Health (AREA)
Transplantation (AREA)
Dermatology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Oral & Maxillofacial Surgery (AREA)
Veterinary Medicine (AREA)
Materials For Medical Uses (AREA)
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Prostheses (AREA)
Eyeglasses (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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SK410-2001A 1998-10-13 1999-10-11 Photocurable siloxane polymers SK4102001A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE9803481A SE9803481D0 (sv)	1998-10-13	1998-10-13	Photocurable siloxane polymers
PCT/EP1999/007781 WO2000022460A1 (en)	1998-10-13	1999-10-11	Photocurable siloxane polymers

Publications (1)

Publication Number	Publication Date
SK4102001A3 true SK4102001A3 (en)	2001-11-06

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ID=20412923

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Application Number	Title	Priority Date	Filing Date
SK410-2001A SK4102001A3 (en)	1998-10-13	1999-10-11	Photocurable siloxane polymers

Country Status (21)

Country	Link
US (2)	US6399734B1 (tr)
EP (1)	EP1137955B1 (tr)
JP (1)	JP2002527171A (tr)
KR (1)	KR100646483B1 (tr)
CN (1)	CN1199057C (tr)
AU (1)	AU759775B2 (tr)
BR (1)	BR9914429B1 (tr)
CA (1)	CA2349566C (tr)
CZ (1)	CZ303236B6 (tr)
EA (1)	EA004653B1 (tr)
HK (1)	HK1040292A1 (tr)
HU (1)	HUP0103942A3 (tr)
ID (1)	ID29222A (tr)
IL (1)	IL142224A (tr)
NO (1)	NO20011836L (tr)
NZ (1)	NZ510810A (tr)
PL (1)	PL347251A1 (tr)
SE (1)	SE9803481D0 (tr)
SK (1)	SK4102001A3 (tr)
TR (1)	TR200101044T2 (tr)
WO (1)	WO2000022460A1 (tr)

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- 1998-10-13 SE SE9803481A patent/SE9803481D0/xx unknown
1999
- 1999-10-11 PL PL99347251A patent/PL347251A1/xx not_active Application Discontinuation
- 1999-10-11 AU AU64724/99A patent/AU759775B2/en not_active Expired
- 1999-10-11 EP EP99952577A patent/EP1137955B1/en not_active Expired - Lifetime
- 1999-10-11 ID IDW00200101046A patent/ID29222A/id unknown
- 1999-10-11 TR TR2001/01044T patent/TR200101044T2/tr unknown
- 1999-10-11 HU HU0103942A patent/HUP0103942A3/hu unknown
- 1999-10-11 JP JP2000576303A patent/JP2002527171A/ja active Pending
- 1999-10-11 NZ NZ510810A patent/NZ510810A/xx not_active IP Right Cessation
- 1999-10-11 CA CA2349566A patent/CA2349566C/en not_active Expired - Lifetime
- 1999-10-11 HK HK02102015.5A patent/HK1040292A1/zh unknown
- 1999-10-11 BR BRPI9914429-8A patent/BR9914429B1/pt not_active IP Right Cessation
- 1999-10-11 WO PCT/EP1999/007781 patent/WO2000022460A1/en not_active Ceased
- 1999-10-11 CN CNB998121215A patent/CN1199057C/zh not_active Expired - Lifetime
- 1999-10-11 KR KR1020017004599A patent/KR100646483B1/ko not_active Expired - Fee Related
- 1999-10-11 CZ CZ20011289A patent/CZ303236B6/cs not_active IP Right Cessation
- 1999-10-11 SK SK410-2001A patent/SK4102001A3/sk unknown
- 1999-10-11 EA EA200100433A patent/EA004653B1/ru not_active IP Right Cessation
- 1999-10-13 US US09/416,773 patent/US6399734B1/en not_active Expired - Lifetime
2001
- 2001-03-22 IL IL142224A patent/IL142224A/en not_active IP Right Cessation
- 2001-04-10 NO NO20011836A patent/NO20011836L/no not_active Application Discontinuation
2002
- 2002-04-29 US US10/134,710 patent/US6737496B2/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CZ303236B6 (cs)	2012-06-13
IL142224A (en)	2007-03-08
KR100646483B1 (ko)	2006-11-14
PL347251A1 (en)	2002-03-25
CA2349566C (en)	2011-01-25
HUP0103942A2 (hu)	2002-02-28
US6399734B1 (en)	2002-06-04
EP1137955A1 (en)	2001-10-04
TR200101044T2 (tr)	2001-08-21
JP2002527171A (ja)	2002-08-27
SE9803481D0 (sv)	1998-10-13
AU759775B2 (en)	2003-05-01
KR20010089296A (ko)	2001-09-29
NO20011836L (no)	2001-06-13
CN1323399A (zh)	2001-11-21
EA004653B1 (ru)	2004-06-24
HK1040292A1 (zh)	2002-05-31
US20030088044A1 (en)	2003-05-08
CN1199057C (zh)	2005-04-27
NO20011836D0 (no)	2001-04-10
NZ510810A (en)	2003-02-28
HUP0103942A3 (en)	2003-05-28
ID29222A (id)	2001-08-16
EA200100433A1 (ru)	2001-10-22
AU6472499A (en)	2000-05-01
CA2349566A1 (en)	2000-04-20
BR9914429A (pt)	2001-06-26
BR9914429B1 (pt)	2011-07-26
EP1137955B1 (en)	2013-01-02
US6737496B2 (en)	2004-05-18
WO2000022460A1 (en)	2000-04-20
CZ20011289A3 (cs)	2001-11-14

Publication	Publication Date	Title
CA2349566C (en)	2011-01-25	Photocurable siloxane polymers
EP1827522B1 (en)	2010-03-17	Compositions for injectable ophthalmic lenses
CN1173194C (zh)	2004-10-27	可注射的眼内镜片
JP2005534737A5 (tr)	2006-09-14
JP2005534737A (ja)	2005-11-17	改良されたバイオ医療品組成物
CN1292805C (zh)	2007-01-03	可注射的眼内透镜
AU2001263848A1 (en)	2002-01-10	Injectable intraocular lens
MXPA01003612A (en)	2002-06-05	Photocurable siloxane polymers
HK1055909A (en)	2004-01-30	Injectable intraocular lens