CA2686938C - Compose d'hydrogel de silicone pour lentilles de contact souples et lentilles de contact souples fabriquees en utilisant le compose - Google Patents
Compose d'hydrogel de silicone pour lentilles de contact souples et lentilles de contact souples fabriquees en utilisant le compose Download PDFInfo
- Publication number
- CA2686938C CA2686938C CA2686938A CA2686938A CA2686938C CA 2686938 C CA2686938 C CA 2686938C CA 2686938 A CA2686938 A CA 2686938A CA 2686938 A CA2686938 A CA 2686938A CA 2686938 C CA2686938 C CA 2686938C
- Authority
- CA
- Canada
- Prior art keywords
- contact lens
- bis
- trimethylsilyl
- acrylamide
- vinyl
- 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 - Fee Related
Links
- 239000000017 hydrogel Substances 0.000 title claims abstract description 19
- 150000001875 compounds Chemical class 0.000 title description 4
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims abstract description 87
- 239000000203 mixture Substances 0.000 claims abstract description 65
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 62
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 59
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims abstract description 51
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims abstract description 44
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims abstract description 41
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims abstract description 39
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims abstract description 38
- 239000000178 monomer Substances 0.000 claims abstract description 25
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 22
- 229920000642 polymer Polymers 0.000 claims description 57
- 239000000126 substance Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 70
- 239000003431 cross linking reagent Substances 0.000 abstract description 36
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 20
- 229910052760 oxygen Inorganic materials 0.000 abstract description 20
- 239000001301 oxygen Substances 0.000 abstract description 20
- 230000035699 permeability Effects 0.000 abstract description 18
- 230000003287 optical effect Effects 0.000 abstract description 4
- 230000005540 biological transmission Effects 0.000 abstract description 3
- 238000006116 polymerization reaction Methods 0.000 description 33
- 239000003999 initiator Substances 0.000 description 23
- 239000000463 material Substances 0.000 description 23
- JUIBLDFFVYKUAC-UHFFFAOYSA-N [5-(2-ethylhexanoylperoxy)-2,5-dimethylhexan-2-yl] 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C(CC)CCCC JUIBLDFFVYKUAC-UHFFFAOYSA-N 0.000 description 19
- 230000036571 hydration Effects 0.000 description 15
- 238000006703 hydration reaction Methods 0.000 description 15
- 238000010521 absorption reaction Methods 0.000 description 9
- 230000003247 decreasing effect Effects 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 210000004087 cornea Anatomy 0.000 description 6
- 230000002209 hydrophobic effect Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000008267 milk Substances 0.000 description 5
- 210000004080 milk Anatomy 0.000 description 5
- 235000013336 milk Nutrition 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 206010011033 Corneal oedema Diseases 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 201000004778 corneal edema Diseases 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 229940093476 ethylene glycol Drugs 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- -1 polypropylene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- 230000001960 triggered effect Effects 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 229940044192 2-hydroxyethyl methacrylate Drugs 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 241000282994 Cervidae Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 206010020675 Hypermetropia Diseases 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 229910007161 Si(CH3)3 Inorganic materials 0.000 description 1
- 229940117913 acrylamide Drugs 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 201000009310 astigmatism Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000004438 eyesight Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000004305 hyperopia Effects 0.000 description 1
- 201000006318 hyperopia Diseases 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 208000001491 myopia Diseases 0.000 description 1
- 230000004379 myopia Effects 0.000 description 1
- PWRKXMFQXZHKFF-UHFFFAOYSA-N n-trimethylsilylprop-2-enamide Chemical compound C[Si](C)(C)NC(=O)C=C PWRKXMFQXZHKFF-UHFFFAOYSA-N 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical compound NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
- A61F2/02—Prostheses implantable into the body
- A61F2/14—Eye parts, e.g. lenses or corneal implants; Artificial eyes
- A61F2/16—Intraocular lenses
-
- 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
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
- C08F226/10—N-Vinyl-pyrrolidone
-
- 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
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Ophthalmology & Optometry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Transplantation (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Optics & Photonics (AREA)
- Vascular Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Eyeglasses (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
La présente invention concerne une composition d'hydrogel de silicone pour une lentille de contact souple et une lentille de contact souple qui utilise cette composition. La composition selon l'invention comprend un monomère de silicone N,O-bis(triméthylsilyl)acrylamide et du méthacrylate de 2-hydroxyéthyle ajouté avec de la N-vinyl-2-pyrrolidone hydrosoluble ou un monomère de N,N-diméthylacrylamide pour améliorer les propriétés hydrophiles et un agent de réticulation tel que le diméthacrylate d'éthylène glycol ou le divinyle benzène pour conférer des propriétés hydrophiles, une teneur en eau élevée, une perméabilité élevée à l'oxygène, un bon allongement et une bonne transmission optique.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2007-0061970 | 2007-06-25 | ||
| KR1020070061970A KR101231181B1 (ko) | 2007-06-25 | 2007-06-25 | 연질 콘텍트렌즈용 실리콘 하이드로겔 조성물 및 그 조성에의해 제조된 연질 콘텍트렌즈 |
| PCT/KR2007/005098 WO2009001987A1 (fr) | 2007-06-25 | 2007-10-18 | Composé d'hydrogel de silicone pour lentilles de contact souples et lentilles de contact souples fabriquées en utilisant le composé |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2686938A1 CA2686938A1 (fr) | 2008-12-31 |
| CA2686938C true CA2686938C (fr) | 2013-04-02 |
Family
ID=40185782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2686938A Expired - Fee Related CA2686938C (fr) | 2007-06-25 | 2007-10-18 | Compose d'hydrogel de silicone pour lentilles de contact souples et lentilles de contact souples fabriquees en utilisant le compose |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP2170992A4 (fr) |
| JP (1) | JP5432133B2 (fr) |
| KR (1) | KR101231181B1 (fr) |
| CN (1) | CN101688042B (fr) |
| AU (1) | AU2007355828B2 (fr) |
| CA (1) | CA2686938C (fr) |
| RU (1) | RU2434899C2 (fr) |
| UA (1) | UA92126C2 (fr) |
| WO (1) | WO2009001987A1 (fr) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5896404B2 (ja) * | 2008-07-21 | 2016-03-30 | ノバルティス アーゲー | 加水分解性基を有するシリコーン含有ポリマー材料 |
| AU2009327484B2 (en) * | 2008-12-18 | 2012-08-09 | Novartis Ag | Method for making silicone hydrogel contact lenses |
| KR101044955B1 (ko) * | 2009-04-06 | 2011-06-29 | 성아영 | 비닐기로 치환된 포스파진을 포함한 고기능 하이드로젤 콘택트렌즈 |
| US8480227B2 (en) * | 2010-07-30 | 2013-07-09 | Novartis Ag | Silicone hydrogel lenses with water-rich surfaces |
| WO2012130956A1 (fr) | 2011-04-01 | 2012-10-04 | Novartis Ag | Composition de formation d'une lentille de contact |
| CN102382226B (zh) * | 2011-08-12 | 2014-03-19 | 天津博纳艾杰尔科技有限公司 | 一种聚n-乙烯吡咯烷酮-二乙烯苯微球的制备方法 |
| US8940812B2 (en) * | 2012-01-17 | 2015-01-27 | Johnson & Johnson Vision Care, Inc. | Silicone polymers comprising sulfonic acid groups |
| US9395468B2 (en) | 2012-08-27 | 2016-07-19 | Ocular Dynamics, Llc | Contact lens with a hydrophilic layer |
| AU2014348502B2 (en) | 2013-11-15 | 2019-08-15 | Tangible Science, Inc. | Contact lens with a hydrophilic layer |
| US9459377B2 (en) * | 2014-01-15 | 2016-10-04 | Johnson & Johnson Vision Care, Inc. | Polymers comprising sulfonic acid groups |
| AU2015201321A1 (en) | 2014-03-31 | 2015-10-15 | Johnson & Johnson Vision Care, Inc. | Silicone acrylamide copolymer |
| AU2015201371A1 (en) * | 2014-03-31 | 2015-10-15 | Johnson & Johnson Vision Care, Inc. | Silicone acrylamide copolymer |
| EP3171836A4 (fr) * | 2014-07-21 | 2018-05-30 | Tangible Science, LLC | Lentilles de contact et procédés de production de lentilles de contact |
| CN107206119B (zh) | 2014-12-09 | 2021-01-29 | 实体科学公司 | 具有生物相容性层的医疗设备涂层 |
| EP4481478A3 (fr) * | 2017-06-07 | 2025-03-26 | Alcon Inc. | Lentilles de contact en hydrogel de silicone |
| WO2018224975A1 (fr) | 2017-06-07 | 2018-12-13 | Novartis Ag | Lentilles de contact en hydrogel de silicone |
| KR101995404B1 (ko) | 2017-08-29 | 2019-07-02 | 대구가톨릭대학교산학협력단 | 고기능성 하이드로겔 콘택트 렌즈 조성물 |
| KR101944717B1 (ko) * | 2017-11-17 | 2019-02-01 | 주식회사 인터로조 | 자외선 차단 기능을 갖는 소프트 콘택트렌즈 및 이의 제조방법 |
| CN117492228A (zh) | 2017-12-13 | 2024-02-02 | 爱尔康公司 | 周抛和月抛水梯度接触镜片 |
| KR102006918B1 (ko) | 2017-12-21 | 2019-08-02 | 주식회사 티씨 싸이언스 | 실리콘 함유 소프트 콘텍트렌즈 제조방법과 상기 방법에 의해 제조된 소프트 콘텍트렌즈 및 상기 소프트 콘텍트렌즈 성형용 조성물 |
| KR20220160733A (ko) | 2021-05-28 | 2022-12-06 | 김영일 | 내구성과 습윤성이 양호하고 상용성이 향상되는 하이드로겔 콘택트렌즈 |
| CN114176895B (zh) * | 2021-11-23 | 2025-01-10 | 天津世纪康泰生物医学工程有限公司 | 一种动物用角膜保护镜 |
| CN115128839B (zh) * | 2022-08-09 | 2025-04-08 | 重庆大学 | 一种基于天然蚕丝制备丝素蛋白隐形眼镜的方法 |
| KR20250110585A (ko) * | 2024-01-12 | 2025-07-21 | 경북대학교 산학협력단 | 아라미드를 포함하는 소프트 콘택트렌즈용 조성물 및 이를 이용한 소프트 콘택트렌즈의 제조 방법 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH578592A5 (fr) * | 1972-10-27 | 1976-08-13 | Ciba Geigy Ag | |
| US4123407A (en) | 1976-11-26 | 1978-10-31 | American Optical Corporation | Hydrophilic contact lens |
| US5314960A (en) * | 1990-04-10 | 1994-05-24 | Permeable Technologies, Inc. | Silicone-containing polymers, oxygen permeable hydrophilic contact lenses and methods for making these lenses and treating patients with visual impairment |
| US5358995A (en) * | 1992-05-15 | 1994-10-25 | Bausch & Lomb Incorporated | Surface wettable silicone hydrogels |
| JPH0756126A (ja) * | 1993-08-20 | 1995-03-03 | Seiko Epson Corp | ソフトコンタクトレンズ |
| JPH07215985A (ja) * | 1994-01-31 | 1995-08-15 | Shin Etsu Chem Co Ltd | トリメチルシリルジエチルアミンの製造方法 |
| US6020445A (en) * | 1997-10-09 | 2000-02-01 | Johnson & Johnson Vision Products, Inc. | Silicone hydrogel polymers |
| US5962548A (en) * | 1998-03-02 | 1999-10-05 | Johnson & Johnson Vision Products, Inc. | Silicone hydrogel polymers |
| CN1950460B (zh) * | 2004-03-05 | 2012-03-14 | 庄臣及庄臣视力保护公司 | 包含无环聚酰胺的润湿性水凝胶 |
| US7786185B2 (en) * | 2004-03-05 | 2010-08-31 | Johnson & Johnson Vision Care, Inc. | Wettable hydrogels comprising acyclic polyamides |
-
2007
- 2007-06-25 KR KR1020070061970A patent/KR101231181B1/ko active Active
- 2007-10-18 CA CA2686938A patent/CA2686938C/fr not_active Expired - Fee Related
- 2007-10-18 CN CN2007800535071A patent/CN101688042B/zh not_active Expired - Fee Related
- 2007-10-18 AU AU2007355828A patent/AU2007355828B2/en not_active Ceased
- 2007-10-18 WO PCT/KR2007/005098 patent/WO2009001987A1/fr not_active Ceased
- 2007-10-18 EP EP07833407A patent/EP2170992A4/fr not_active Withdrawn
- 2007-10-18 JP JP2010514580A patent/JP5432133B2/ja not_active Expired - Fee Related
- 2007-10-18 UA UAA201000666A patent/UA92126C2/ru unknown
- 2007-10-18 RU RU2009146491/05A patent/RU2434899C2/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| JP5432133B2 (ja) | 2014-03-05 |
| RU2434899C2 (ru) | 2011-11-27 |
| KR101231181B1 (ko) | 2013-02-07 |
| CN101688042A (zh) | 2010-03-31 |
| KR20080113467A (ko) | 2008-12-31 |
| EP2170992A4 (fr) | 2010-08-04 |
| AU2007355828A1 (en) | 2008-12-31 |
| JP2010531474A (ja) | 2010-09-24 |
| WO2009001987A1 (fr) | 2008-12-31 |
| EP2170992A1 (fr) | 2010-04-07 |
| CA2686938A1 (fr) | 2008-12-31 |
| CN101688042B (zh) | 2012-01-11 |
| AU2007355828B2 (en) | 2011-03-03 |
| AU2007355828A8 (en) | 2010-03-18 |
| UA92126C2 (ru) | 2010-09-27 |
| RU2009146491A (ru) | 2011-07-27 |
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