JP5432133B2 - 軟質コンタクトレンズ用シリコンヒドロゲルのための単量体組成物およびその単量体組成物により製造された軟質コンタクトレンズ - Google Patents
軟質コンタクトレンズ用シリコンヒドロゲルのための単量体組成物およびその単量体組成物により製造された軟質コンタクトレンズ Download PDFInfo
- Publication number
- JP5432133B2 JP5432133B2 JP2010514580A JP2010514580A JP5432133B2 JP 5432133 B2 JP5432133 B2 JP 5432133B2 JP 2010514580 A JP2010514580 A JP 2010514580A JP 2010514580 A JP2010514580 A JP 2010514580A JP 5432133 B2 JP5432133 B2 JP 5432133B2
- Authority
- JP
- Japan
- Prior art keywords
- bis
- trimethylsilyl
- acrylamide
- monomer composition
- 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.)
- Active
Links
- 239000000178 monomer Substances 0.000 title claims description 40
- 239000000203 mixture Substances 0.000 title claims description 37
- 239000000017 hydrogel Substances 0.000 title claims description 22
- 229910052710 silicon Inorganic materials 0.000 title claims description 20
- 239000010703 silicon Substances 0.000 title claims description 20
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims description 19
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 55
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 50
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 44
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 43
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 36
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 36
- 239000000126 substance Substances 0.000 claims description 17
- 229920001296 polysiloxane Polymers 0.000 claims description 8
- -1 N, N-bis (trimethylsilyl) acrylamide (N, N-Bis (trimethylsilyl) acrylamide) Chemical compound 0.000 claims description 7
- ZBGFFOJGTVCHFT-UHFFFAOYSA-N N,N-dimethylprop-2-enamide Chemical compound CN(C(C=C)=O)C.CN(C(C=C)=O)C ZBGFFOJGTVCHFT-UHFFFAOYSA-N 0.000 claims description 4
- VKJWJILXLWFQEU-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene Chemical compound C=CC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C VKJWJILXLWFQEU-UHFFFAOYSA-N 0.000 claims 1
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 79
- OAGHFLPWSOJXTL-UHFFFAOYSA-N n,n-bis(trimethylsilyl)prop-2-enamide Chemical compound C[Si](C)(C)N([Si](C)(C)C)C(=O)C=C OAGHFLPWSOJXTL-UHFFFAOYSA-N 0.000 description 61
- 229920000642 polymer Polymers 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- 238000006116 polymerization reaction Methods 0.000 description 32
- 239000003431 cross linking reagent Substances 0.000 description 28
- 230000001965 increasing effect Effects 0.000 description 26
- 239000003999 initiator Substances 0.000 description 22
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 18
- 229910052760 oxygen Inorganic materials 0.000 description 18
- 239000001301 oxygen Substances 0.000 description 18
- 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 16
- 230000035699 permeability Effects 0.000 description 16
- 230000036571 hydration Effects 0.000 description 13
- 238000006703 hydration reaction Methods 0.000 description 13
- 239000011259 mixed solution Substances 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 10
- 230000000704 physical effect Effects 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 7
- 239000004971 Cross linker Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 230000003247 decreasing effect Effects 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 210000004087 cornea Anatomy 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
- 230000008859 change Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 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
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 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
- 230000000694 effects Effects 0.000 description 2
- 210000001508 eye Anatomy 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 1
- WNXTZVMMNCCZTP-UHFFFAOYSA-N 2-hydroxyethyl 2-methylprop-2-enoate 5-hydroxy-2-methylpent-2-enoic acid Chemical compound OCCC=C(C(=O)O)C.C(C(=C)C)(=O)OCCO WNXTZVMMNCCZTP-UHFFFAOYSA-N 0.000 description 1
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 1
- 241000282994 Cervidae Species 0.000 description 1
- 206010020675 Hypermetropia Diseases 0.000 description 1
- 201000009310 astigmatism Diseases 0.000 description 1
- 210000005252 bulbus oculi Anatomy 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000002708 enhancing effect Effects 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
- 230000036541 health Effects 0.000 description 1
- QFOJTGAPBXCVOK-UHFFFAOYSA-N hexyl 2-ethylhexaneperoxoate Chemical compound CCCCCCOOC(=O)C(CC)CCCC QFOJTGAPBXCVOK-UHFFFAOYSA-N 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 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
- 230000007774 longterm Effects 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 208000001491 myopia Diseases 0.000 description 1
- 230000004379 myopia Effects 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000010069 protein adhesion Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003376 silicon Chemical class 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical compound NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 0.000 description 1
- 230000004304 visual acuity Effects 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, corneal implants; Implanting instruments specially adapted therefor; 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 |
|---|---|---|---|
| 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 (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 |
|---|---|
| JP2010531474A JP2010531474A (ja) | 2010-09-24 |
| JP5432133B2 true JP5432133B2 (ja) | 2014-03-05 |
Family
ID=40185782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010514580A Active JP5432133B2 (ja) | 2007-06-25 | 2007-10-18 | 軟質コンタクトレンズ用シリコンヒドロゲルのための単量体組成物およびその単量体組成物により製造された軟質コンタクトレンズ |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP2170992A4 (uk) |
| JP (1) | JP5432133B2 (uk) |
| KR (1) | KR101231181B1 (uk) |
| CN (1) | CN101688042B (uk) |
| AU (1) | AU2007355828B2 (uk) |
| CA (1) | CA2686938C (uk) |
| RU (1) | RU2434899C2 (uk) |
| UA (1) | UA92126C2 (uk) |
| WO (1) | WO2009001987A1 (uk) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010011493A1 (en) * | 2008-07-21 | 2010-01-28 | Novartis Ag | Silicone-containing polymeric materals with hydrolyzable groups |
| KR101422900B1 (ko) * | 2008-12-18 | 2014-07-30 | 노파르티스 아게 | 실리콘 히드로겔 콘택트 렌즈의 제조 방법 |
| KR101044955B1 (ko) * | 2009-04-06 | 2011-06-29 | 성아영 | 비닐기로 치환된 포스파진을 포함한 고기능 하이드로젤 콘택트렌즈 |
| TWI648571B (zh) * | 2010-07-30 | 2019-01-21 | 諾華公司 | 水合隱形鏡片 |
| WO2012130956A1 (en) | 2011-04-01 | 2012-10-04 | 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 |
| EP3988992A1 (en) | 2013-11-15 | 2022-04-27 | 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 |
| CA2955012A1 (en) * | 2014-07-21 | 2016-01-28 | Tangible Science Llc | Contact lenses and methods of making contact lenses |
| AU2015360637B2 (en) | 2014-12-09 | 2019-08-22 | Tangible Science, Inc. | Medical device coating with a biocompatible layer |
| MX2019014537A (es) * | 2017-06-07 | 2020-08-17 | Alcon Inc | Lentes de contacto de hidrogel de silicona. |
| RU2769703C2 (ru) | 2017-06-07 | 2022-04-05 | Алькон Инк. | Силикон-гидрогелевые контактные линзы |
| 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 |
| BR112020009607A2 (pt) | 2017-12-13 | 2020-10-13 | Alcon Inc. | lentes de contato com gradiente aquoso descartáveis semanal e mensalmente |
| 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 |
| CN114176895A (zh) * | 2021-11-23 | 2022-03-15 | 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 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH578592A5 (uk) * | 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 IP Right Grant
- 2007-10-18 AU AU2007355828A patent/AU2007355828B2/en active Active
- 2007-10-18 RU RU2009146491/05A patent/RU2434899C2/ru active
- 2007-10-18 UA UAA201000666A patent/UA92126C2/uk unknown
- 2007-10-18 EP EP07833407A patent/EP2170992A4/en not_active Withdrawn
- 2007-10-18 JP JP2010514580A patent/JP5432133B2/ja active Active
- 2007-10-18 WO PCT/KR2007/005098 patent/WO2009001987A1/en active Application Filing
- 2007-10-18 CN CN2007800535071A patent/CN101688042B/zh active Active
- 2007-10-18 CA CA2686938A patent/CA2686938C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2686938C (en) | 2013-04-02 |
| UA92126C2 (uk) | 2010-09-27 |
| WO2009001987A1 (en) | 2008-12-31 |
| CN101688042A (zh) | 2010-03-31 |
| CN101688042B (zh) | 2012-01-11 |
| EP2170992A1 (en) | 2010-04-07 |
| AU2007355828A1 (en) | 2008-12-31 |
| RU2009146491A (ru) | 2011-07-27 |
| AU2007355828B2 (en) | 2011-03-03 |
| KR20080113467A (ko) | 2008-12-31 |
| CA2686938A1 (en) | 2008-12-31 |
| KR101231181B1 (ko) | 2013-02-07 |
| EP2170992A4 (en) | 2010-08-04 |
| RU2434899C2 (ru) | 2011-11-27 |
| AU2007355828A8 (en) | 2010-03-18 |
| JP2010531474A (ja) | 2010-09-24 |
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