WO2008134674A1 - Uv-absorbers for ophthalmic lens materials - Google Patents
Uv-absorbers for ophthalmic lens materials Download PDFInfo
- Publication number
- WO2008134674A1 WO2008134674A1 PCT/US2008/061844 US2008061844W WO2008134674A1 WO 2008134674 A1 WO2008134674 A1 WO 2008134674A1 US 2008061844 W US2008061844 W US 2008061844W WO 2008134674 A1 WO2008134674 A1 WO 2008134674A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ophthalmic device
- disubstituted
- device material
- formula
- triazole compound
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
Definitions
- This invention is directed to ultraviolet light absorbers.
- this invention relates to 1 ,4-disubstituted-1 ,2,3-triazole UV light absorbing monomers.
- UV light absorbers are known as ingredients for polymeric materials used to make ophthalmic lenses. UV absorbers are preferably covalently bound to the polymeric network of the lens material instead of simply physically entrapped in the material to prevent the absorber from migrating, phase separating or leaching out of the lens material. Such stability is particularly important for implantable ophthalmic lenses where the leaching of the UV absorber may present both toxicological issues and lead to the loss of UV blocking activity in the implant.
- UV absorbers Numerous copolymerizable benzatriazole, benzophenone and triazine UV absorbers are known. Many of these UV absorbers contain conventional olefinic polymerizable groups, such as methacrylate, acrylate, methacrylamide, acrylamide or styrene groups. Copolymerization with other ingredients in the lens materials, typically with a radical initiator, incorporates the UV absorbers into the resulting polymer chain. Incorporation of additional functional groups, on a UV absorber may influence one or more of the UV absorber's UV absorbing properties, solubility or reactivity.
- the UV absorber may coalesce into domains that could interact with light and result in decreased optical clarity of the lens.
- Examples of polymeric ophthalmic lens materials that incorporate UV absorbers can be found in U.S. Patent Nos. 5,290,892; 5,331 ,073 and 5,693,095.
- the present invention provides 1 ,4-disubstituted-1 ,2,3-triazole UV light absorbing monomers. These UV absorbers are suitable for use in ophthalmic lenses, including contact lenses. They are particularly useful in implantable lenses, such as intraocular lenses (1OLs).
- UV absorbers of the present invention are represented by the formula
- x is 1 - 12;
- Y is H, CH 3 , CH 2 OH, or CH 3 CH 2 ;
- Z is O, NH, N(CH 3 ), or N(CH 2 CH 3 );
- Z' is O, NH, N(CH 3 ), or N(CH 2 CH 3 );
- R" is H, F, Cl, Br, I 1 O(CH 2 ) X H, NH 2 , NH(CH 3 ), N(CH 3 ) 2 , CH 3 , CH 2 CH 3 ,
- Preferred UV absorbers of the present invention are those of formulas [1] - [3]:
- x is 1 - 12;
- Z is O, NH, N(CH 3 ), or N(CH 2 CH 3 ); and R 2 is H, F, Cl, Br, I, O(CH 2 ) X H, NH 2 , NH(CH 3 ), N(CH 3 ) 2 , CH 3 , CH 2 CH 3 , CH(CHs) 2 , C(CH 3 ) 3 , C 6 H 5 , or OC 6 H 5 ;
- R 3 is H, F, Cl, Br, I, O(CH 2 ) X H, NH 2 , NH(CH 3 ), N(CH 3 ) 2 , CH 3 , CH 2 CH 3 , CH(CH 3 ) 2 , C(CHs) 3 , C 6 H 5 , or OC 6 H 5 ;
- x is 1 - 12;
- Y is H, CH 3 , or CH 3 CH 2 ; and Z is O, NH, N(CH 3 ), or N(CH 2 CH 3 );
- R 6 is H, F, Cl 1 Br, I 1 O(CH 2 ) X H, NH 2 , NH(CH 3 ), N(CH 3 ) 2 , CH 3 , CH 2 CH 3 ,
- Z is O 1 NH, N(CH 3 ), N(CH 2 CH 3 ), or nothing;
- an aliphatic azide is coupled with an o- alkynylphenol in a single step to produce the target phenyl substituted 1 ,2,3- triazole where the placement of the phenol group next to the triazole is considered for desired UV absorbance characteristics.
- azidoethyl methacrylate with 2-ethynyl-phenol will produce a 1 ,2,3-triazole functional polymerizable UV absorber in a single step.
- Additional hydroxyl functionality is envisioned through use of propanediol or glycerol based aliphatic azides.
- Scheme 2 presents the combination of a substituted phenolic azide and an aliphatic alkyne.
- a substituted phenolic azide for example, coupling of propargyl methacrylate with o-azidophenol in the presence of CuBr will result in the target triazole functional polymerizable UV absorber.
- both aromatic radicals for example, propargyl methacrylate with o-azidophenol in the presence of CuBr will result in the target triazole functional polymerizable UV absorber.
- I 5 from aromatic azide and aliphatic alkyne.
- the UV absorbers of the present invention are particularly suitable for use in 1OLs.
- IOL materials will generally contain from 0.1 to 5 % (w/w) of a UV absorber of the present invention.
- IOL materials will contain from 0.5 to 3 % (w/w) of a UV absorber of the present invention.
- Such device materials are prepared by copolymerizing the UV absorbers of the present invention with other ingredients, such as device-forming materials, cross- linking agents, and blue-light blocking chromophores.
- any known IOL device material is suitable for use in the compositions of the present invention.
- the ophthalmic device materials comprise an acrylic or methacrylic device-forming monomer. More preferably, the device-forming monomers comprise a monomer of formula [IV]:
- A is H, CH 3 , CH 2 CH 3 , or CH 2 OH;
- B is (CH 2 ) m or [O(CH 2 ) 2 ] Z ;
- C is (CH 2 ) W ;
- m is 2 - 6;
- z is 1 - 10;
- Y is nothing, O, S, or NR', provided that if Y is O, S, or NR', then
- B is (CH 2 ) m ;
- D is H, Ci - C 4 alkyl, Ci - C 4 alkoxy, C 6 H 5 , CH 2 C 6 H 5 or halogen.
- Preferred monomers of formula [IV] are those wherein A is H or CH 3 , B is (CH 2 ) m , m is 2 - 5, Y is nothing or O, w is O - 1 , and D is H. Most preferred are 2-phenylethyl methacrylate; 4-phenylbutyl methacrylate; 5-phenylpentyl methacrylate; 2-benzyloxyethyl methacrylate; and 3-benzyloxypropyl methacrylate;and their corresponding acrylates.
- Monomers of formula [IV] are known and can be made by known methods.
- the conjugate alcohol of the desired monomer can be combined in a reaction vessel with methyl methacrylate, tetrabutyl titanate
- Device materials generally comprise a total of at least about 75%, preferably at least about 80%, of device-forming monomers.
- the device materials of the present invention generally comprise a cross-linking agent.
- the cross-linking agent used in the device materials of this invention may be any terminally ethylenically unsaturated compound having more than one unsaturated group.
- the total amount of the cross-linking component is at least
- 0.1 % by weight and, depending on the identity and concentration of the remaining components and the desired physical properties, can range to about 20% by weight.
- the preferred concentration range for the cross-linking component is 0.1 - 17% (w/w).
- Suitable polymerization initiators for device materials containing a UV absorber of the present invention include thermal initiators and photoinitiators.
- Preferred thermal initiators include peroxy free-radical initiators, such as t-butyl (peroxy-2-ethyl)hexanoate and di-(tert-butylcyclohexyl) peroxydicarbonate (commercially available as Perkadox ® 16 from Akzo Chemicals Inc., Chicago, Illinois). Initiators are typically present in an amount of about 5% (w/w) or less. Because free-radical initiators do not become chemically a part of the polymers formed, the total amount of initiator is customarily not included when determining the amounts of other ingredients.
- the device materials containing a UV absorber of the present invention preferably also contain a reactive colorant.
- Suitable reactive blue-light absorbing compounds include those described in U.S. Patent No. 5,470,932. Blue-light absorbers are typically present in an amount from about 0.01 - 0.5 % (weight).
- the IOLs constructed of the materials of the present invention can be of any design capable of being rolled or folded into a small cross section that can fit through a relatively smaller incision.
- the IOLs can be of what is known as a one piece or multipiece design, and comprise optic and haptic components.
- the optic is that portion which serves as the lens.
- the haptics are attached to the optic and hold the optic in its proper place in the eye.
- the optic and haptic(s) can be of the same or different material.
- a multipiece lens is so called because the optic and the haptic(s) are made separately and then the haptics are attached to the optic.
- the optic and the haptics are formed out of one piece of material. Depending on the material, the haptics are then cut, or lathed, out of the material to produce the 1OL.
- the materials of the present invention are also suitable for use in other ophthalmic devices, such as contact lenses, keratoprostheses, and corneal inlays or rings.
- a 100 ml round bottom flask containing a PTFE coated stir bar is charged with 3.1Og of azido ethyl methacrylate (20 mmol), 2.36 g of o-hydroxyphenyl acetylene (20 mmol) and 50 mL of tetrahydrofuran. Copper turnings (1 g) were weighed and added. The flask was closed with a glass stopper and the reaction was stirred 48 h at ambient temperature. The copper was removed and the solvent was evaporated to yield product UV-1.
- a 100 ml round bottom flask containing a PTFE coated stir bar is charged with 5.09 g of 3-azido-2-azidomethyl-2-hydroxymethyl-propyl methacrylate (20 mmol), 2.36 g of o-hydroxyphenyl acetylene (20 mmol) and 50 ml_ of tetrahydrofuran. Copper turnings (1 g) are added and the solution is stirred for 48 h at ambient temperature. The copper was removed and the solvent was evaporated to yield product UV-2.
- a 100 ml round bottom flask containing a PTFE coated stir bar is flushed with N2 and charged with 2.48 g of propargyl methacrylate (20 mmol), 2.70 g of 2- azidophenol (20 mmol), 50 ml_ of N,N-dimethylformamide, 3.54 g of N 1 N 1 N 1 N", N"-pentamethyldiethylenetriamine, and 2.87 g of CuBr .
- the solution is stirred for 24 h at ambient temperature under a N 2 blanket.
- the reaction mixture is then exposed to air and purified by passing through a chromatographic alumina column. The eluent is collected and the solvent is evaporated to yield product UV-3.
- a vial is charged with ingredients as listed in Table 1 except for the initiator.
- the solution is mixed thoroughly and de-gassed by bubbling with N 2 .
- the initiator is added and the solution is again mixed thoroughly.
- the solution is filtered through a 0.2 micron PTFE filter and transferred to polypropylene molds.
- the molds are heated in a mechanical convection oven at 70 0 C for 1 hr, then 110 0 C for 2 hrs.
- the resulting copolymer samples are removed from the polypropylene molds and extracted in refluxing acetone for at least 3 hr, then rinsed with fresh acetone and allowed to air dry.
- the extracted polymer is dried under vacuum at 70 0 C for at least 3 hr.
- PEA 2-phenylethyl acrylate
- PBMA 4-phenylbutyl methacrylate
- HEMA 2-hydroxyethyl methacrylate
- PEG(1000)DMA polyethylene glycol (1000) dimethacrylate
- EGDMA ethylene glycol dimethacrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Materials For Medical Uses (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Eyeglasses (AREA)
- Optical Filters (AREA)
- Prostheses (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE602008002426T DE602008002426D1 (en) | 2007-04-30 | 2008-04-29 | UV ABSORBER FOR GLASSES OF GLASSES |
AU2008245533A AU2008245533B2 (en) | 2007-04-30 | 2008-04-29 | UV-absorbers for ophthalmic lens materials |
JP2010506567A JP5273748B2 (en) | 2007-04-30 | 2008-04-29 | UV absorber for ophthalmic lens material |
CA2683002A CA2683002C (en) | 2007-04-30 | 2008-04-29 | Uv-absorbers for ophthalmic lens materials |
AT08747077T ATE479664T1 (en) | 2007-04-30 | 2008-04-29 | UV ABSORBER FOR GLASS LENS MATERIAL |
EP08747077A EP2139871B1 (en) | 2007-04-30 | 2008-04-29 | Uv-absorbers for ophthalmic lens materials |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US91492307P | 2007-04-30 | 2007-04-30 | |
US60/914,923 | 2007-04-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2008134674A1 true WO2008134674A1 (en) | 2008-11-06 |
Family
ID=39559880
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2008/061844 WO2008134674A1 (en) | 2007-04-30 | 2008-04-29 | Uv-absorbers for ophthalmic lens materials |
Country Status (9)
Country | Link |
---|---|
US (2) | US7909458B2 (en) |
EP (1) | EP2139871B1 (en) |
JP (1) | JP5273748B2 (en) |
AT (1) | ATE479664T1 (en) |
AU (1) | AU2008245533B2 (en) |
CA (1) | CA2683002C (en) |
DE (1) | DE602008002426D1 (en) |
ES (1) | ES2349182T3 (en) |
WO (1) | WO2008134674A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009083457A1 (en) * | 2007-12-28 | 2009-07-09 | Basf Se | Novel functionalized (meth)acrylic monomers and polymers from acetylenic alcohols |
JP2010235928A (en) * | 2009-03-09 | 2010-10-21 | Sumitomo Chemical Co Ltd | Polymer and method for producing polymer |
WO2011069931A1 (en) | 2009-12-09 | 2011-06-16 | Basf Se | Formulation of light-sensitive pesticides and comb polymers containing a uv absorber |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW200916531A (en) * | 2007-08-09 | 2009-04-16 | Alcon Inc | Ophthalmic lens materials containing chromophores that absorb both UV and short wavelength visible light |
TWI435915B (en) * | 2007-08-09 | 2014-05-01 | Alcon Inc | Ophthalmic lens materials containing chromophores that absorb both uv and short wavelength visible light |
EP2247976B1 (en) * | 2008-02-12 | 2012-08-08 | Aaren Scientific Inc. | Ophthalmic lens having a yellow dye light blocking component |
US7803359B1 (en) | 2008-05-06 | 2010-09-28 | Alcon, Inc. | UV-absorbers for ophthalmic lens materials |
US8043607B2 (en) | 2008-07-15 | 2011-10-25 | Novartis Ag | UV-absorbers for ophthalmic lens materials |
US8236053B1 (en) | 2008-10-08 | 2012-08-07 | Novartis Ag | 2-amino benzophenone UV-absorbers for ophthalmic lens materials |
TWI453199B (en) * | 2008-11-04 | 2014-09-21 | Alcon Inc | Uv/visible light absorbers for ophthalmic lens materials |
TWI464151B (en) * | 2009-07-06 | 2014-12-11 | Alcon Inc | Uv/visible light absorbers for ophthalmic lens materials |
US8993698B2 (en) * | 2009-07-08 | 2015-03-31 | Isp Investments Inc. | 4- and 5 substituted 1,2,3-triazole moieties with at least one remote polymerizable moiety and polymers thereof |
TW201311621A (en) | 2011-08-15 | 2013-03-16 | Novartis Ag | UV-absorbers for ophthalmic lens materials |
US8585938B1 (en) | 2012-03-30 | 2013-11-19 | Novartis Ag | UV-absorbers for ophthalmic lens materials |
CN106620893B (en) * | 2015-07-23 | 2021-07-30 | 爱博诺德(北京)医疗科技股份有限公司 | Materials for ocular disease phototherapy |
CA3064161A1 (en) | 2017-06-13 | 2018-12-20 | Alcon Inc. | Intraocular lens compositions |
JP2019112533A (en) * | 2017-12-24 | 2019-07-11 | 国立大学法人千葉大学 | Copolymer that allows noble metal separation recovery, and noble metal recovery method using the copolymer |
EP3894909A4 (en) | 2018-12-10 | 2023-04-05 | Seed Co., Ltd. | Uv absorbing ocular lens |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2099154A5 (en) * | 1970-06-17 | 1972-03-10 | Gaf Corp | |
US3880875A (en) * | 1969-08-28 | 1975-04-29 | Albert F Strobel | Ultraviolet absorbing 2-(2-hydroxyphenyl) 2H-1,2,3-triazole derivatives |
EP0989124A1 (en) * | 1998-09-25 | 2000-03-29 | Daicel Chemical Industries, Ltd. | New polyester compounds having a benzotriazole group and a preparation method thereof |
Family Cites Families (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IN139845B (en) * | 1972-11-06 | 1976-08-07 | Bayer Ag | |
DE3019521A1 (en) * | 1980-05-22 | 1981-11-26 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING V-TRIAZOLE COMPOUNDS |
US5290892A (en) | 1990-11-07 | 1994-03-01 | Nestle S.A. | Flexible intraocular lenses made from high refractive index polymers |
US5331073A (en) | 1992-11-09 | 1994-07-19 | Allergan, Inc. | Polymeric compositions and intraocular lenses made from same |
US5470932A (en) | 1993-10-18 | 1995-11-28 | Alcon Laboratories, Inc. | Polymerizable yellow dyes and their use in opthalmic lenses |
JP3206004B2 (en) * | 1995-06-07 | 2001-09-04 | アルコン ラボラトリーズ, インコーポレイテッド | Improved high refractive index ophthalmic lens materials |
JPH09146244A (en) * | 1995-11-21 | 1997-06-06 | Konica Corp | Image formation of silver halide photographic sensitive material |
US6166218A (en) | 1996-11-07 | 2000-12-26 | Ciba Specialty Chemicals Corporation | Benzotriazole UV absorbers having enhanced durability |
JP4149068B2 (en) | 1999-03-02 | 2008-09-10 | 株式会社メニコン | Ophthalmic lens material |
CN1151186C (en) | 1999-09-07 | 2004-05-26 | 爱尔康通用有限公司 | Foldable ophthalmic and otorhinolaryngological device materials |
US20020042653A1 (en) | 1999-11-23 | 2002-04-11 | Copeland Victor L. | Blue blocking intraocular lens implant |
US6638991B2 (en) | 2000-03-22 | 2003-10-28 | Menicon Co., Ltd. | Material for ocular lens |
US6908978B2 (en) | 2001-11-02 | 2005-06-21 | Bausch & Lomb Incorporated | High refractive index polymeric siloxysilane compositions |
US6762271B2 (en) | 2001-11-02 | 2004-07-13 | Bausch & Lomb Incorporated | High refractive index aromatic-based silyl monomers |
EP2226316B1 (en) | 2002-05-30 | 2016-01-13 | The Scripps Research Institute | Copper-catalysed ligation of azides and acetylenes |
US6852793B2 (en) | 2002-06-19 | 2005-02-08 | Bausch & Lomb Incorporated | Low water content, high refractive index, flexible, polymeric compositions |
DK1521786T3 (en) | 2002-07-16 | 2008-07-28 | Alcon Inc | Materials for ophthalmic and otorhinolaryngological devices |
CA2512586A1 (en) | 2003-01-09 | 2004-07-29 | Alcon, Inc. | Dual function uv-absorbers for ophthalmic lens materials |
JP2005053058A (en) | 2003-08-04 | 2005-03-03 | Fuji Photo Film Co Ltd | Optical information recording medium and information recording method |
US6872793B1 (en) | 2003-08-07 | 2005-03-29 | Alcon, Inc. | Ophthalmic and otorhinolaryngological device materials |
EP1694721B1 (en) | 2003-11-05 | 2013-10-09 | Benz Research and Development Corporation | Materials for making hydrophobic intraocular lens |
JP4457030B2 (en) * | 2004-02-26 | 2010-04-28 | 富士フイルム株式会社 | Planographic printing plate precursor and lithographic printing plate manufacturing method |
ATE549649T1 (en) | 2004-11-22 | 2012-03-15 | Abbott Medical Optics Inc | COPOLYMERIZABLE AZONE COMPOUNDS AND ITEMS CONTAINING THEM |
CN1727338A (en) | 2004-12-27 | 2006-02-01 | 常州华钛化学有限公司 | Compound in benzotriazole category possessing alkenyl ester type structure, and preparation method |
US20060252850A1 (en) | 2005-05-04 | 2006-11-09 | Bausch & Lomb Incorporated | Radiation-absorbing polymeric materials and ophthalmic devices comprising same |
EP1877840A4 (en) | 2005-05-05 | 2010-05-19 | Key Medical Technologies Inc | Ophthalmic apparatuses and methods |
US7842367B2 (en) | 2005-05-05 | 2010-11-30 | Key Medical Technologies, Inc. | Ultra violet, violet, and blue light filtering polymers for ophthalmic applications |
JP4636955B2 (en) * | 2005-07-06 | 2011-02-23 | キヤノン株式会社 | Air processing apparatus and image forming system |
US20070092830A1 (en) | 2005-10-24 | 2007-04-26 | Bausch & Lomb Incorporated | Polymeric radiation-absorbing materials and ophthalmic devices comprising same |
US20070092831A1 (en) | 2005-10-24 | 2007-04-26 | Bausch & Lomb Incorporated | Radiation-absorbing polymeric materials and ophthalmic devices comprising same |
AU2007311172B2 (en) | 2006-10-13 | 2013-01-31 | Alcon Inc. | Intraocular lenses with unique blue-violet cutoff and blue light transmission characteristics |
ES2699166T3 (en) | 2007-03-05 | 2019-02-07 | Benz Res And Development Corporation | Light filters that comprise a chromophore found in nature and its derivatives |
JP2009013148A (en) | 2007-07-03 | 2009-01-22 | Shipro Kasei Kaisha Ltd | Chemical modification to bis type structure by adipoyl dichloride, isophthaloyl dichloride or terephthaloyl dichloride of benzotriazole-based ultraviolet light absorbent having hydroxymethyl group |
TWI435915B (en) * | 2007-08-09 | 2014-05-01 | Alcon Inc | Ophthalmic lens materials containing chromophores that absorb both uv and short wavelength visible light |
-
2008
- 2008-04-29 AU AU2008245533A patent/AU2008245533B2/en not_active Ceased
- 2008-04-29 US US12/111,321 patent/US7909458B2/en active Active
- 2008-04-29 ES ES08747077T patent/ES2349182T3/en active Active
- 2008-04-29 DE DE602008002426T patent/DE602008002426D1/en active Active
- 2008-04-29 WO PCT/US2008/061844 patent/WO2008134674A1/en active Application Filing
- 2008-04-29 EP EP08747077A patent/EP2139871B1/en active Active
- 2008-04-29 AT AT08747077T patent/ATE479664T1/en not_active IP Right Cessation
- 2008-04-29 JP JP2010506567A patent/JP5273748B2/en active Active
- 2008-04-29 CA CA2683002A patent/CA2683002C/en not_active Expired - Fee Related
-
2011
- 2011-01-11 US US13/004,373 patent/US8115009B2/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3880875A (en) * | 1969-08-28 | 1975-04-29 | Albert F Strobel | Ultraviolet absorbing 2-(2-hydroxyphenyl) 2H-1,2,3-triazole derivatives |
FR2099154A5 (en) * | 1970-06-17 | 1972-03-10 | Gaf Corp | |
EP0989124A1 (en) * | 1998-09-25 | 2000-03-29 | Daicel Chemical Industries, Ltd. | New polyester compounds having a benzotriazole group and a preparation method thereof |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009083457A1 (en) * | 2007-12-28 | 2009-07-09 | Basf Se | Novel functionalized (meth)acrylic monomers and polymers from acetylenic alcohols |
JP2010235928A (en) * | 2009-03-09 | 2010-10-21 | Sumitomo Chemical Co Ltd | Polymer and method for producing polymer |
WO2011069931A1 (en) | 2009-12-09 | 2011-06-16 | Basf Se | Formulation of light-sensitive pesticides and comb polymers containing a uv absorber |
Also Published As
Publication number | Publication date |
---|---|
CA2683002C (en) | 2014-05-20 |
CA2683002A1 (en) | 2008-11-06 |
US20110105765A1 (en) | 2011-05-05 |
EP2139871B1 (en) | 2010-09-01 |
AU2008245533B2 (en) | 2012-06-28 |
JP5273748B2 (en) | 2013-08-28 |
AU2008245533A1 (en) | 2008-11-06 |
US7909458B2 (en) | 2011-03-22 |
US20080266519A1 (en) | 2008-10-30 |
DE602008002426D1 (en) | 2010-10-14 |
ES2349182T3 (en) | 2010-12-28 |
EP2139871A1 (en) | 2010-01-06 |
US8115009B2 (en) | 2012-02-14 |
ATE479664T1 (en) | 2010-09-15 |
JP2010526077A (en) | 2010-07-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP2139871B1 (en) | Uv-absorbers for ophthalmic lens materials | |
AU2008283862B2 (en) | Ophthalmic lens materials containing chromophores that absorb both UV and short wavelength visible light | |
US8262947B2 (en) | UV/visible light absorbers for ophthalmic lens materials | |
US7781571B2 (en) | Ophthalmic lens materials containing chromophores that absorb both UV and short wavelength visible light | |
WO2010053917A1 (en) | Uv/visible light absorbers for ophthalmic lens materials | |
US8585938B1 (en) | UV-absorbers for ophthalmic lens materials | |
WO2011005713A2 (en) | Visible light absorbers for ophthalmic lens materials | |
US20100207068A1 (en) | Process for producing purified synthesis gas from synthesis gas comprising trace amounts of sulphur contaminants with a metal-organic framework | |
EP2941419A1 (en) | Uv-absorbers for ophthalmic lens materials | |
WO2013025671A1 (en) | Uv-absorbers for ophthalmic lens materials |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 08747077 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2683002 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2008747077 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2008245533 Country of ref document: AU |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2010506567 Country of ref document: JP |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: 2008245533 Country of ref document: AU Date of ref document: 20080429 Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 12676475 Country of ref document: US |