JP2005501171A - 高ｕｖ波長保護用途のための低色調の紫外線吸収剤 - Google Patents
高ｕｖ波長保護用途のための低色調の紫外線吸収剤 Download PDFInfo
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Classifications
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33365—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing cyano group
- C08G65/33368—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing cyano group acyclic
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2612—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aromatic or arylaliphatic hydroxyl 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/3311—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group
- C08G65/3318—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group heterocyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
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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)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Organic Insulating Materials (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/934,377 US6602447B2 (en) | 2001-08-21 | 2001-08-21 | Low-color ultraviolet absorbers for high UV wavelength protection applications |
| PCT/US2002/023514 WO2003019075A1 (en) | 2001-08-21 | 2002-07-24 | Low-color ultraviolet absorbers for high uv wavelength protection applications |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005501171A true JP2005501171A (ja) | 2005-01-13 |
| JP2005501171A5 JP2005501171A5 (https=) | 2006-01-05 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003523899A Pending JP2005501171A (ja) | 2001-08-21 | 2002-07-24 | 高ｕｖ波長保護用途のための低色調の紫外線吸収剤 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6602447B2 (https=) |
| EP (1) | EP1419347B1 (https=) |
| JP (1) | JP2005501171A (https=) |
| KR (1) | KR20040036727A (https=) |
| CN (1) | CN100340589C (https=) |
| AT (1) | ATE330170T1 (https=) |
| BR (1) | BR0211599B1 (https=) |
| DE (1) | DE60212403T2 (https=) |
| WO (1) | WO2003019075A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2015002151A1 (ja) * | 2013-07-01 | 2017-02-23 | 株式会社明治 | 飲食品等の光安定性の向上方法 |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6602447B2 (en) * | 2001-08-21 | 2003-08-05 | Milliken & Company | Low-color ultraviolet absorbers for high UV wavelength protection applications |
| US7097789B2 (en) * | 2001-08-21 | 2006-08-29 | Milliken & Company | Thermoplastic containers exhibiting excellent protection to various ultraviolet susceptible compounds |
| CN1554197A (zh) * | 2001-09-11 | 2004-12-08 | �ʼҷ����ֵ��ӹɷ�����˾ | 具有液体光学滤光器的图像投影设备 |
| EP1451248B1 (en) * | 2001-11-30 | 2008-11-26 | Ciba Holding Inc. | 2-hydroxyphenyl-s-triazine crosslinkers for polymer networks |
| US6835333B2 (en) * | 2002-05-07 | 2004-12-28 | Milliken & Company | Combinations for use as toners in polyesters |
| US7094918B2 (en) * | 2003-04-28 | 2006-08-22 | Milliken & Company | Low-color ultraviolet absorbers for thermoplastic and thermoset high UV wavelength protection applications |
| US20050010017A1 (en) * | 2003-07-11 | 2005-01-13 | Blakely Dale Milton | Addition of UV inhibitors to pet process for maximum yield |
| US7074396B2 (en) * | 2003-10-22 | 2006-07-11 | Access Business Group International Llc | Composition and method for protecting both natural and artificial hair color from ultraviolet light damage |
| US7504054B2 (en) | 2003-12-11 | 2009-03-17 | Bayer Materialscience Llc | Method of treating a plastic article |
| US20050249904A1 (en) * | 2004-01-23 | 2005-11-10 | Rajnish Batlaw | Articles and process of making polypropylene articles having ultraviolet light protection by injection stretch blow molding of polypropylene |
| US20050277759A1 (en) * | 2004-05-27 | 2005-12-15 | Pearson Jason C | Process for adding furyl-2-methylidene UV light absorbers to poly(ethylene terephthalate) |
| US20050277716A1 (en) * | 2004-05-27 | 2005-12-15 | Pearson Jason C | Furyl-2-methylidene UV absorbers and compositions incorporating the UV absorbers |
| US7541407B2 (en) * | 2004-05-27 | 2009-06-02 | Eastman Chemical Company | Process for adding methine UV light absorbers to PET prepared by direct esterification |
| US20050267283A1 (en) * | 2004-05-27 | 2005-12-01 | Weaver Max A | Process for adding nitrogen containing methine light absorbers to poly(ethylene terephthalate) |
| US7763265B2 (en) * | 2004-06-30 | 2010-07-27 | Dak Americas, Llc | UV barrier formulation for polyesters |
| US20060029815A1 (en) * | 2004-07-21 | 2006-02-09 | Woodruff Daniel P | Substrate coating |
| US7642303B2 (en) * | 2004-10-15 | 2010-01-05 | Shakely Thomas L | Thermoplastic articles for packaging UV sensitive materials, processes for the articles production and use and novel UV absorbers |
| EP1739119A1 (en) | 2005-06-29 | 2007-01-03 | Bayer MaterialScience AG | Process for the treatment of plastic profiles |
| US7600813B2 (en) * | 2005-12-19 | 2009-10-13 | Polymer Packaging, Inc. | Temporary protective seat cover |
| US20090089942A1 (en) | 2007-10-09 | 2009-04-09 | Bayer Materialscience Llc | Method of tinting a plastic article |
| US8298675B2 (en) | 2009-07-17 | 2012-10-30 | Honda Motor Co., Ltd. | Low gloss wood for interior trim |
| US20110014444A1 (en) * | 2009-07-17 | 2011-01-20 | Jessica Alessandro | Uv protecting treatment for wooden interior trim |
| US11173688B2 (en) * | 2011-06-02 | 2021-11-16 | Essel Propack Ltd. | Ultra violet light resistant laminate, and process of manufacturing the same |
| MY178371A (en) * | 2014-09-25 | 2020-10-09 | Kowa Co | Pharmaceutical preparation |
| KR101907970B1 (ko) * | 2017-04-10 | 2018-10-16 | 주식회사 엘엠에스 | 광학물품 및 이를 포함하는 광학필터 |
Family Cites Families (86)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3159646A (en) * | 1960-01-13 | 1964-12-01 | American Cyanamid Co | Alkenoylamido and oxy phenylbenzotriazoles |
| US3120564A (en) * | 1960-01-13 | 1964-02-04 | American Cyanamid Co | Alkenoylamino benzophenones |
| US3072585A (en) * | 1960-01-13 | 1963-01-08 | American Cyanamid Co | Vinylbenzyloxy phenylbenzotriazoles |
| NL266092A (https=) | 1960-12-21 | |||
| DE1170143B (de) * | 1961-08-24 | 1964-05-14 | Ruetgerswerke Ag | Verfahren zur Herstellung ungesaettigter Polyester |
| US3234233A (en) | 1962-07-27 | 1966-02-08 | Rexall Drug Chemical | Substituted bicycloheptane-2, 3-dicarboximides |
| US3201363A (en) | 1962-09-20 | 1965-08-17 | Hercules Powder Co Ltd | Extrusion aids for polyethylene |
| US3367926A (en) | 1964-03-25 | 1968-02-06 | Dow Chemical Co | Modification of crystalline structure of crystallizable high polymers |
| US3408341A (en) | 1964-10-21 | 1968-10-29 | Eastman Kodak Co | Crystallinity promoters |
| US3320267A (en) | 1964-10-21 | 1967-05-16 | Mcneilab Inc | 2, 3-dicarboxylic acid and derivatives of norbornanes and the corresponding norbornenes |
| US3546270A (en) | 1965-07-23 | 1970-12-08 | Geigy Chem Corp | Bis-methylene malonic acid nitriles |
| US3382183A (en) * | 1965-09-02 | 1968-05-07 | American Cyanamid Co | Plastic optical filter |
| US3517086A (en) | 1966-01-31 | 1970-06-23 | Sumitomo Chemical Co | Nucleated blend of polypropylene,polyethylene,and ethylene propylene copolymer |
| GB1204729A (en) | 1967-12-28 | 1970-09-09 | Shell Int Research | Process for the improvement of synthetic diene polymers |
| CH491991A (de) | 1968-10-04 | 1970-06-15 | Bayer Ag | Verwendung von Tetracarbonsäureestern zum Schützen organischer Stoffe gegen UV-Strahlung |
| BE755237A (nl) | 1969-08-28 | 1971-02-01 | Noury & Van Der Lande | Nieuwe u.v. absorberende verbindingen |
| GB1318520A (en) | 1969-11-27 | 1973-05-31 | Ici Ltd | Chemical compositions |
| DE2002489A1 (de) | 1970-01-21 | 1971-07-29 | Huels Chemische Werke Ag | Kristallisationsfaehige thermoplastische Massen |
| JPS531319B1 (https=) | 1971-03-16 | 1978-01-18 | ||
| US3829450A (en) | 1972-11-01 | 1974-08-13 | Universal Oil Prod Co | Polyhalosubstituted polyhydropolycyclicdicarboxylic acid and anhydride |
| US3873643A (en) | 1972-12-18 | 1975-03-25 | Chemplex Co | Graft copolymers of polyolefins and cyclic acid and acid anhydride monomers |
| US3882194A (en) | 1973-01-26 | 1975-05-06 | Chemplex Co | Cografted copolymers of a polyolefin, an acid or acid anhydride and an ester monomer |
| US3880992A (en) | 1973-12-19 | 1975-04-29 | Cpc International Inc | Mixture useful on a sunscreen composition |
| US3941746A (en) | 1973-12-28 | 1976-03-02 | Ciba-Geigy Corporation | Containing hindered phenolic norbornane-2,3-dicarboximides stabilized compositions |
| US3933779A (en) | 1974-02-21 | 1976-01-20 | Fine Organics Inc. | Antistatic polymer blend |
| US3954913A (en) | 1975-01-06 | 1976-05-04 | The Standard Oil Company | Stabilized nitrile polymers |
| JPS51133400A (en) | 1975-05-15 | 1976-11-19 | Japan Synthetic Rubber Co Ltd | A process for manufacturing animpact resistant thermoplastic resin |
| CH615911A5 (https=) | 1975-06-18 | 1980-02-29 | Ciba Geigy Ag | |
| JPS58445B2 (ja) | 1975-10-17 | 1983-01-06 | 三井化学株式会社 | 熱可塑性エラストマ−の製造方法 |
| JPS5340760A (en) | 1976-09-28 | 1978-04-13 | Teijin Ltd | Preparation of unsaturated imide esters |
| US4284729A (en) | 1980-03-31 | 1981-08-18 | Milliken Research Corporation | Process for coloring thermosetting resins |
| JPS5718682A (en) | 1980-07-08 | 1982-01-30 | Mitsui Toatsu Chem Inc | Preparation of bis p-ethylbenzylidene sorbitol |
| EP0057160B1 (de) | 1981-01-23 | 1985-06-19 | Ciba-Geigy Ag | 2-(2-Hydroxyphenyl)-benztriazole, ihre Verwendung als UV-Absorber und ihre Herstellung |
| US4853471A (en) | 1981-01-23 | 1989-08-01 | Ciba-Geigy Corporation | 2-(2-Hydroxyphenyl)-benztriazoles, their use as UV-absorbers and their preparation |
| US4496757A (en) | 1981-11-05 | 1985-01-29 | Ciba-Geigy Corporation | Ultraviolet-absorbing stabilizers substituted an aliphatic hydroxyl group |
| US4452942A (en) | 1982-02-19 | 1984-06-05 | Chemplex Company | Adhesive blends containing anacid or anhydride grafted LLDPE |
| JPS58160343A (ja) | 1982-03-17 | 1983-09-22 | Nippon Ester Co Ltd | ポリエステル組成物 |
| DE3215911A1 (de) | 1982-04-29 | 1983-11-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zur behandlung von (co)polymerisaten zur entfernung von restmonomeren |
| US4476184A (en) | 1983-08-09 | 1984-10-09 | The Boeing Company | Thermally stable polysulfone compositions for composite structures |
| WO1986000313A1 (fr) * | 1984-06-25 | 1986-01-16 | Washi Kosan Co., Ltd. | Plaque en plastique absorbant les rayons ultraviolets |
| JPS6117834A (ja) | 1984-07-04 | 1986-01-25 | Matsushita Electric Ind Co Ltd | ガステ−ブル |
| US4617374A (en) | 1985-02-15 | 1986-10-14 | Eastman Kodak Company | UV-absorbing condensation polymeric compositions and products therefrom |
| US4619990A (en) | 1985-03-11 | 1986-10-28 | Minnesota Mining And Manufacturing Company | Polymeric dyes with pendent chromophore groups capable of undergoing thermoplastic deformation |
| US4778837A (en) | 1985-05-03 | 1988-10-18 | American Cyanamid Company | Low basicity hindered amine light stabilizers |
| US4704421A (en) | 1985-08-06 | 1987-11-03 | El Paso Products Company | Nucleation of propylene polymers |
| US4732570A (en) | 1985-09-13 | 1988-03-22 | Milliken Research Corporation | Colored thermoplastic resin |
| US4739017A (en) | 1986-06-06 | 1988-04-19 | The Dow Chemical Company | Retro Diels Alder assisted polymer grafting process |
| US4801637A (en) | 1986-06-18 | 1989-01-31 | Shell Oil Company | Nucleation process for inducing crystallization in poly(alpha olefins) |
| DE3775893D1 (de) | 1986-11-11 | 1992-02-20 | Ici Plc | Mischung aus einer carbonsaeure und einem amin. |
| US4716234A (en) * | 1986-12-01 | 1987-12-29 | Iolab Corporation | Ultraviolet absorbing polymers comprising 2-(2'-hydroxy-5'-acryloyloxyalkoxyphenyl)-2H-benzotriazole |
| DE3739523A1 (de) | 1986-12-02 | 1988-06-16 | Sandoz Ag | Substituierte oxalsaeuredianilide und ihre verwendung als lichtstabilisatoren |
| US5057491A (en) | 1987-12-16 | 1991-10-15 | California Institute Of Technology | High current density tunnel junction fabrication from high temperature superconducting oxides |
| JPH01180514A (ja) | 1988-01-13 | 1989-07-18 | Hitachi Chem Co Ltd | 眼鏡レンズ用樹脂組成物及び眼鏡レンズ |
| GB8905796D0 (en) | 1988-03-29 | 1989-04-26 | Ici Plc | Composition and use |
| US5057627A (en) | 1988-06-09 | 1991-10-15 | Shell Oil Company | Alkoxylation process catalyzed by phosphate salts of the rare earth elements |
| US4845188A (en) | 1988-08-19 | 1989-07-04 | Eastman Kodak Company | Condensation polymers containing methine ultraviolet radiation-absorbing residues and shaped articles produced therefrom |
| JPH0826485B2 (ja) | 1989-08-11 | 1996-03-13 | 帝人株式会社 | 香りを有する芯鞘型中実複合短繊維 |
| US5057594A (en) | 1989-08-17 | 1991-10-15 | Eastman Kodak Company | Ultraviolet light-absorbing compounds and sunscreen formulations and polymeric materials containing such compounds or residues thereof |
| US5135975A (en) | 1989-09-20 | 1992-08-04 | Milliken Research Corporation | Bis(3,4-dialkylbenzylidene) sorbitol acetals and compositions containing same |
| FR2656620B1 (fr) | 1990-01-04 | 1992-04-24 | M & T Chemicals Inc | Composition de resine synthetique polyolefinique contenant un agent nucleant. |
| JPH05139460A (ja) | 1991-11-15 | 1993-06-08 | Daito Nitto Kk | 徐放性薬剤封入袋 |
| JP3226333B2 (ja) | 1992-06-29 | 2001-11-05 | 富士通株式会社 | 弾性表面波素子 |
| US5459222A (en) | 1993-06-04 | 1995-10-17 | Ciba-Geigy Corporation | UV-absorbing polyurethanes and polyesters |
| JP3401888B2 (ja) | 1993-12-20 | 2003-04-28 | 新日本理化株式会社 | ポリオレフィン系樹脂組成物 |
| GB9411800D0 (en) | 1994-06-13 | 1994-08-03 | Sandoz Ltd | Organic compounds |
| US5468793A (en) | 1994-07-25 | 1995-11-21 | Wico Corporation | Plastic compositions with antistatic properties |
| US5543083A (en) | 1994-07-26 | 1996-08-06 | The Procter & Gamble Company | Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation |
| US5585228A (en) | 1994-11-30 | 1996-12-17 | Eastman Kodak Company | Benzotriazole based UV absorbing compounds and photographic elements containing them |
| JPH08239509A (ja) * | 1995-03-06 | 1996-09-17 | Fuji Photo Film Co Ltd | ポリマーフィルム |
| US5756010A (en) * | 1996-06-20 | 1998-05-26 | Eastman Kodak Company | Protective eyeshield |
| US5922793A (en) | 1996-12-27 | 1999-07-13 | Minnesota Mining And Manufacturing Company | Modifying agents for polyolefins |
| US5929146A (en) | 1996-12-27 | 1999-07-27 | Minnesota Mining And Manufacturing Company | Modifying agents for polyolefins |
| JP3714574B2 (ja) | 1997-03-26 | 2005-11-09 | ダイセル化学工業株式会社 | 紫外線吸収剤とその製造方法および合成樹脂組成物 |
| US6008302A (en) * | 1997-04-29 | 1999-12-28 | 3M Innovative Properties Company | Polyolefin bound ultraviolet light absorbers |
| US6229252B1 (en) * | 1999-01-21 | 2001-05-08 | Asahi Glass Company, Limited | Dye combinations for multiple bandpass filters for video displays |
| US6113813A (en) * | 1999-03-11 | 2000-09-05 | Goudjil; Kamal | Photochromic ultraviolet protective shield |
| US6207740B1 (en) * | 1999-07-27 | 2001-03-27 | Milliken & Company | Polymeric methine ultraviolet absorbers |
| JP2001213918A (ja) * | 2000-02-04 | 2001-08-07 | Nisshinbo Ind Inc | 近赤外吸収組成物及び該組成物より製造した近赤外吸収フィルター |
| DE60125656T2 (de) * | 2000-07-31 | 2007-04-26 | Fuji Photo Film Co. Ltd., Minamiashigara | Fluoreszente Lampenabdeckung und Beleuchtungseinrichtung |
| US6301055B1 (en) * | 2000-08-16 | 2001-10-09 | California Institute Of Technology | Solid immersion lens structures and methods for producing solid immersion lens structures |
| US6307055B1 (en) * | 2000-12-27 | 2001-10-23 | Council Of Scientific And Industrial Research | Diol-functionalized UV absorber |
| EP1369712B1 (en) * | 2001-02-23 | 2006-06-14 | Dainippon Ink And Chemicals, Inc. | Color filter |
| WO2003018682A1 (en) * | 2001-08-21 | 2003-03-06 | Milliken & Company | Low-color ultraviolet absorber compounds and compositions thereof |
| US6602447B2 (en) * | 2001-08-21 | 2003-08-05 | Milliken & Company | Low-color ultraviolet absorbers for high UV wavelength protection applications |
| US6596795B2 (en) | 2001-08-21 | 2003-07-22 | Milliken & Company | Low-color vanillin-based ultraviolet absorbers and methods of making thereof |
| US6559216B1 (en) | 2001-08-21 | 2003-05-06 | Milliken & Company | Low-color ultraviolet absorber compounds and compositions thereof |
-
2001
- 2001-08-21 US US09/934,377 patent/US6602447B2/en not_active Expired - Lifetime
-
2002
- 2002-07-24 KR KR10-2004-7002581A patent/KR20040036727A/ko not_active Ceased
- 2002-07-24 JP JP2003523899A patent/JP2005501171A/ja active Pending
- 2002-07-24 CN CNB028159802A patent/CN100340589C/zh not_active Expired - Lifetime
- 2002-07-24 DE DE60212403T patent/DE60212403T2/de not_active Expired - Lifetime
- 2002-07-24 BR BRPI0211599-9A patent/BR0211599B1/pt not_active IP Right Cessation
- 2002-07-24 EP EP02750282A patent/EP1419347B1/en not_active Expired - Lifetime
- 2002-07-24 WO PCT/US2002/023514 patent/WO2003019075A1/en not_active Ceased
- 2002-07-24 AT AT02750282T patent/ATE330170T1/de not_active IP Right Cessation
- 2002-12-31 US US10/334,857 patent/US7014797B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2015002151A1 (ja) * | 2013-07-01 | 2017-02-23 | 株式会社明治 | 飲食品等の光安定性の向上方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1419347A4 (en) | 2005-03-30 |
| DE60212403D1 (de) | 2006-07-27 |
| US7014797B2 (en) | 2006-03-21 |
| KR20040036727A (ko) | 2004-04-30 |
| DE60212403T2 (de) | 2007-02-01 |
| US20030136949A1 (en) | 2003-07-24 |
| BR0211599B1 (pt) | 2012-08-07 |
| BR0211599A (pt) | 2004-11-30 |
| EP1419347B1 (en) | 2006-06-14 |
| CN100340589C (zh) | 2007-10-03 |
| US6602447B2 (en) | 2003-08-05 |
| ATE330170T1 (de) | 2006-07-15 |
| CN1543550A (zh) | 2004-11-03 |
| US20030075709A1 (en) | 2003-04-24 |
| EP1419347A1 (en) | 2004-05-19 |
| WO2003019075A1 (en) | 2003-03-06 |
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