CA2686938C - Silicone-hydrogel compound for soft contact lens and soft contact lens produced using the compound - Google Patents
Silicone-hydrogel compound for soft contact lens and soft contact lens produced using the compound 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020070061970A KR101231181B1 (ko) | 2007-06-25 | 2007-06-25 | 연질 콘텍트렌즈용 실리콘 하이드로겔 조성물 및 그 조성에의해 제조된 연질 콘텍트렌즈 |
| KR10-2007-0061970 | 2007-06-25 | ||
| PCT/KR2007/005098 WO2009001987A1 (en) | 2007-06-25 | 2007-10-18 | Silicone-hydrogel compound for soft contact lens and soft contact lens produced using the compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2686938A1 CA2686938A1 (en) | 2008-12-31 |
| CA2686938C true CA2686938C (en) | 2013-04-02 |
Family
ID=40185782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2686938A Expired - Fee Related CA2686938C (en) | 2007-06-25 | 2007-10-18 | Silicone-hydrogel compound for soft contact lens and soft contact lens produced using the compound |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP2170992A4 (de) |
| JP (1) | JP5432133B2 (de) |
| KR (1) | KR101231181B1 (de) |
| CN (1) | CN101688042B (de) |
| AU (1) | AU2007355828B2 (de) |
| CA (1) | CA2686938C (de) |
| RU (1) | RU2434899C2 (de) |
| UA (1) | UA92126C2 (de) |
| WO (1) | WO2009001987A1 (de) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2730506A1 (en) * | 2008-07-21 | 2010-01-28 | Novartis Ag | Silicone-containing polymeric materials with hydrolyzable groups |
| TWI613067B (zh) * | 2008-12-18 | 2018-02-01 | 諾華公司 | 適合製造聚矽氧水凝膠隱形眼鏡的形成鏡片組合物 |
| KR101044955B1 (ko) * | 2009-04-06 | 2011-06-29 | 성아영 | 비닐기로 치환된 포스파진을 포함한 고기능 하이드로젤 콘택트렌즈 |
| SG187026A1 (en) | 2010-07-30 | 2013-02-28 | Novartis Ag | A silicone hydrogel lens with a crosslinked hydrophilic coating |
| US8618187B2 (en) | 2011-04-01 | 2013-12-31 | Novartis Ag | Composition for forming a contact lens |
| 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 |
| JP2017505922A (ja) | 2013-11-15 | 2017-02-23 | タンジブル サイエンス リミテッド ライアビリティ カンパニー | 親水性層を有するコンタクトレンズ |
| US9459377B2 (en) * | 2014-01-15 | 2016-10-04 | Johnson & Johnson Vision Care, Inc. | Polymers comprising sulfonic acid groups |
| AU2015201371A1 (en) * | 2014-03-31 | 2015-10-15 | Johnson & Johnson Vision Care, Inc. | Silicone acrylamide copolymer |
| AU2015201321A1 (en) * | 2014-03-31 | 2015-10-15 | Johnson & Johnson Vision Care, Inc. | Silicone acrylamide copolymer |
| EP3171836A4 (de) * | 2014-07-21 | 2018-05-30 | Tangible Science, LLC | Kontaktlinsen und verfahren zur herstellung von kontaktlinsen |
| EP3229851A4 (de) | 2014-12-09 | 2018-08-01 | Tangible Science LLC | Beschichtung einer medizinischen vorrichtung mit biokompatibler schicht |
| KR20250012724A (ko) * | 2017-06-07 | 2025-01-24 | 알콘 인코포레이티드 | 실리콘 하이드로겔 콘택트 렌즈 |
| TWI723635B (zh) | 2017-06-07 | 2021-04-01 | 瑞士商愛爾康公司 | 矽酮水凝膠接觸鏡片 |
| 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 |
| HUE062978T2 (hu) | 2017-12-13 | 2023-12-28 | Alcon Inc | Eljárás MPS-kompatibilis víz-grádienst tartalmazó kontaktlencsék elõállítására |
| 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 (de) | 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 |
| US7786185B2 (en) * | 2004-03-05 | 2010-08-31 | Johnson & Johnson Vision Care, Inc. | Wettable hydrogels comprising acyclic polyamides |
| 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 |
-
2007
- 2007-06-25 KR KR1020070061970A patent/KR101231181B1/ko active Active
- 2007-10-18 EP EP07833407A patent/EP2170992A4/de not_active Withdrawn
- 2007-10-18 WO PCT/KR2007/005098 patent/WO2009001987A1/en not_active Ceased
- 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 AU AU2007355828A patent/AU2007355828B2/en not_active Ceased
- 2007-10-18 CA CA2686938A patent/CA2686938C/en not_active Expired - Fee Related
- 2007-10-18 RU RU2009146491/05A patent/RU2434899C2/ru active
- 2007-10-18 CN CN2007800535071A patent/CN101688042B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| UA92126C2 (ru) | 2010-09-27 |
| RU2009146491A (ru) | 2011-07-27 |
| JP2010531474A (ja) | 2010-09-24 |
| CA2686938A1 (en) | 2008-12-31 |
| AU2007355828B2 (en) | 2011-03-03 |
| RU2434899C2 (ru) | 2011-11-27 |
| CN101688042B (zh) | 2012-01-11 |
| KR20080113467A (ko) | 2008-12-31 |
| EP2170992A4 (de) | 2010-08-04 |
| AU2007355828A1 (en) | 2008-12-31 |
| AU2007355828A8 (en) | 2010-03-18 |
| JP5432133B2 (ja) | 2014-03-05 |
| WO2009001987A1 (en) | 2008-12-31 |
| KR101231181B1 (ko) | 2013-02-07 |
| CN101688042A (zh) | 2010-03-31 |
| EP2170992A1 (de) | 2010-04-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20211018 |