CA2343226A1 - Polyalkoxylated naphthopyrans - Google Patents

Polyalkoxylated naphthopyrans Download PDF

Info

Publication number
CA2343226A1
CA2343226A1 CA002343226A CA2343226A CA2343226A1 CA 2343226 A1 CA2343226 A1 CA 2343226A1 CA 002343226 A CA002343226 A CA 002343226A CA 2343226 A CA2343226 A CA 2343226A CA 2343226 A1 CA2343226 A1 CA 2343226A1
Authority
CA
Canada
Prior art keywords
compounds
naphtho
pyrans
polyalkoxylated
indeno
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.)
Granted
Application number
CA002343226A
Other languages
French (fr)
Other versions
CA2343226C (en
Inventor
Barry Van Gemert
Kevin J. Stewart
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Transitions Optical Inc
Original Assignee
Ppg Industries Ohio, Inc.
Barry Van Gemert
Kevin J. Stewart
Ppg Industries, Inc.
Transitions Optical, Inc.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ppg Industries Ohio, Inc., Barry Van Gemert, Kevin J. Stewart, Ppg Industries, Inc., Transitions Optical, Inc. filed Critical Ppg Industries Ohio, Inc.
Publication of CA2343226A1 publication Critical patent/CA2343226A1/en
Application granted granted Critical
Publication of CA2343226C publication Critical patent/CA2343226C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/23—Photochromic filters

Abstract

Described are novel photochromic polyalkoxylated naphthopyran compounds, examples of which are certain 2H-naphtho[1,2-b]pyrans, 3H-naphtho[2,1-b]pyrans and indeno[2,1-f]naphtho[1,2-b]pyrans, each having at least one polyalkoxylated substituent of from 2 to 50 alkoxy units per substituent. Specific substituents may also be present on the naphtho, indeno and pyrano portions of the compounds. These compounds may be represented by graphic formulae (I), (II) or (III). Also described are various substrates, e.g., paper, glass, organic polymeric materials, etc., that contain or that are coated with such compounds. Optically clear articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel naphthopyran compounds or combinations thereof with complementary photochromic compounds, e.g., certain other naphthopyrans, indenonaphthopyrans, benzopyrans, oxazine-type compounds, etc., are also described.
CA002343226A 1998-09-11 1999-09-09 Polyalkoxylated naphthopyrans Expired - Lifetime CA2343226C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/151,982 1998-09-11
US09/151,982 US5961892A (en) 1998-09-11 1998-09-11 Polyalkoxylated naphthopyrans
PCT/US1999/020664 WO2000015630A1 (en) 1998-09-11 1999-09-09 Polyalkoxylated naphthopyrans

Publications (2)

Publication Number Publication Date
CA2343226A1 true CA2343226A1 (en) 2000-03-23
CA2343226C CA2343226C (en) 2005-11-15

Family

ID=22541091

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002343226A Expired - Lifetime CA2343226C (en) 1998-09-11 1999-09-09 Polyalkoxylated naphthopyrans

Country Status (10)

Country Link
US (1) US5961892A (en)
EP (1) EP1112264B1 (en)
JP (1) JP4550281B2 (en)
AU (1) AU758378B2 (en)
BR (1) BR9913868A (en)
CA (1) CA2343226C (en)
CO (1) CO5221040A1 (en)
DE (1) DE69904211T2 (en)
ES (1) ES2188241T3 (en)
WO (1) WO2000015630A1 (en)

Families Citing this family (79)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE59810912D1 (en) * 1997-09-22 2004-04-08 Rodenstock Gmbh PHOTOCHROME NAPHTHOPYRAN DYES, METHOD FOR THE PRODUCTION THEREOF, THEIR USE AND A PHOTOCHROME OBJECT
US6268055B1 (en) * 1997-12-08 2001-07-31 Ppg Industries Ohio, Inc. Photochromic epoxy resin coating composition and articles having such a coating
US6555028B2 (en) 1998-09-11 2003-04-29 Transitions Optical, Inc. Polymeric matrix compatibilized naphthopyrans
FR2783249B1 (en) 1998-09-11 2001-06-22 Flamel Tech Sa C5-C6 ANNELED NAPHTHOPYRANS, THEIR PREPARATION AND THE POLYMERIC COMPOSITIONS AND (CO) MATRICES CONTAINING THEM
FR2794749A1 (en) 1999-06-10 2000-12-15 Corning Sa BENZOPYRANES C7-C8 RINGED WITH AN AROMATIC HETEROCYCLE AND THE POLYMERIC COMPOSITIONS AND MATRIX (CO) CONTAINING THEM
FR2794748B1 (en) 1999-06-10 2001-09-21 Corning Sa C5-C6 ANNELED NAPHTHOPYRANS WITH A LACTAM-TYPE C6 CYCLE AND THE POLYMERIC COMPOSITIONS AND MATRICES (CO) CONTAINING THEM
US6348604B1 (en) 1999-09-17 2002-02-19 Ppg Industries Ohio, Inc. Photochromic naphthopyrans
US6296785B1 (en) 1999-09-17 2001-10-02 Ppg Industries Ohio, Inc. Indeno-fused photochromic naphthopyrans
EP1144416B1 (en) * 1999-11-10 2005-03-02 Rodenstock GmbH Heterocyclically anellated indenochromene derivatives
EP1265885B1 (en) * 2000-03-22 2005-06-22 Transitions Optical, Inc. Hydroxylated/carboxylated naphthopyrans
US6686468B2 (en) * 2000-09-14 2004-02-03 Optische Werke G. Rodenstock H-annellated benzo[f]chromenes
US6736998B2 (en) 2000-12-29 2004-05-18 Transitions Optical, Inc. Indeno-fused photochromic naphthopyrans
US20030141490A1 (en) * 2001-12-21 2003-07-31 Walters Robert W. Photochromic polymer compositions and articles thereof
US7638554B2 (en) * 2002-04-18 2009-12-29 Sri International Flavanoids as chemotherapeutic, chemopreventive, and antiangiogenic agents
US20030229136A1 (en) * 2002-04-18 2003-12-11 Nurulain Zaveri Novel flavanoids as chemotherapeutic, chemopreventive, and antiangiogenic agents
US7320826B2 (en) * 2003-03-20 2008-01-22 Ppg Industries Ohio, Inc. Photochromic articles with reduced temperature dependency and methods for preparation
US20040186241A1 (en) * 2003-03-20 2004-09-23 Gemert Barry Van Photochromic ocular devices
US7262295B2 (en) 2003-03-20 2007-08-28 Transitions Optical, Inc. Indeno-fused photochromic naphthopyrans, naphthols and photochromic articles
US9096014B2 (en) 2003-07-01 2015-08-04 Transitions Optical, Inc. Oriented polymeric sheets exhibiting dichroism and articles containing the same
US8518546B2 (en) 2003-07-01 2013-08-27 Transitions Optical, Inc. Photochromic compounds and compositions
US8211338B2 (en) 2003-07-01 2012-07-03 Transitions Optical, Inc Photochromic compounds
US7632540B2 (en) 2003-07-01 2009-12-15 Transitions Optical, Inc. Alignment facilities for optical dyes
US8582192B2 (en) 2003-07-01 2013-11-12 Transitions Optical, Inc. Polarizing photochromic articles
US8545984B2 (en) * 2003-07-01 2013-10-01 Transitions Optical, Inc. Photochromic compounds and compositions
US8698117B2 (en) 2003-07-01 2014-04-15 Transitions Optical, Inc. Indeno-fused ring compounds
US20110140056A1 (en) 2003-07-01 2011-06-16 Transitions Optical, Inc. Indeno-fused ring compounds
US7342112B2 (en) * 2003-07-01 2008-03-11 Ppg Industries Ohio, Inc. Photochromic compounds
US7256921B2 (en) * 2003-07-01 2007-08-14 Transitions Optical, Inc. Polarizing, photochromic devices and methods of making the same
WO2005028465A1 (en) * 2003-09-18 2005-03-31 Tokuyama Corporation Chromene compound
US20070187656A1 (en) * 2004-04-30 2007-08-16 Polymers Australia Pty Limited Photochromic compositions and articles comprising siloxane, alkylene or substituted alkylene oligomers
US20070159594A9 (en) * 2004-05-13 2007-07-12 Jani Dharmendra M Photochromic blue light filtering materials and ophthalmic devices
US9052438B2 (en) 2005-04-08 2015-06-09 Johnson & Johnson Vision Care, Inc. Ophthalmic devices comprising photochromic materials with reactive substituents
US20060228557A1 (en) * 2005-04-08 2006-10-12 Beon-Kyu Kim Photochromic materials having extended pi-conjugated systems and compositions and articles including the same
US20060226402A1 (en) * 2005-04-08 2006-10-12 Beon-Kyu Kim Ophthalmic devices comprising photochromic materials having extended PI-conjugated systems
US9139552B2 (en) 2005-04-08 2015-09-22 Transitions Optical, Inc. Indeno-fused naphthopyrans having ethylenically unsaturated groups
US7556750B2 (en) 2005-04-08 2009-07-07 Transitions Optical, Inc. Photochromic materials with reactive substituents
US9028728B2 (en) 2005-04-08 2015-05-12 Transitions Optical, Inc. Photochromic materials that include indeno-fused naphthopyrans
US8158037B2 (en) 2005-04-08 2012-04-17 Johnson & Johnson Vision Care, Inc. Photochromic materials having extended pi-conjugated systems and compositions and articles including the same
US8647538B2 (en) 2005-04-08 2014-02-11 Transitions Optical, Inc. Photochromic compounds having at least two photochromic moieties
US8147725B2 (en) 2005-04-08 2012-04-03 Transitions Optical, Inc Photochromic materials having extended pi-conjugated systems and compositions and articles including the same
WO2008105306A1 (en) 2007-02-22 2008-09-04 Tokuyama Corporation Coating composition and photochromic optical article
US7961372B2 (en) * 2007-08-24 2011-06-14 Lg Chem, Ltd. Photochromic films and method for manufacturing the same
EP2602300B1 (en) 2010-08-06 2019-06-12 Tokuyama Corporation Photochromic composition
US9034219B2 (en) 2010-12-16 2015-05-19 Transitions Optical, Inc. Photochromic compounds and compositions
US8920928B2 (en) 2010-12-16 2014-12-30 Transitions Optical, Inc. Photochromic compounds and compositions
MX2013011788A (en) 2011-04-13 2014-03-26 Tokuyama Corp Photochromic composition.
US9513407B2 (en) 2011-04-18 2016-12-06 Tokuyama Corporation Photochromic composition and optical article using photochromic composition
CN102993156B (en) * 2011-09-19 2014-10-15 天津孚信科技有限公司 Preparation method of aryl-substituted-naphthopyran photochromic compounds
AU2012327127B2 (en) 2011-10-17 2015-12-17 Tokuyama Corporation (meth)acrylate compound and photochromic curable composition containing the (meth)acrylate compound
WO2013099640A1 (en) 2011-12-26 2013-07-04 株式会社トクヤマ Photochromic composition
US8691915B2 (en) 2012-04-23 2014-04-08 Sabic Innovative Plastics Ip B.V. Copolymers and polymer blends having improved refractive indices
WO2013161642A1 (en) 2012-04-27 2013-10-31 株式会社トクヤマ Photochromic curable composition
JP6355209B2 (en) 2013-03-04 2018-07-11 株式会社トクヤマ Photochromic curable composition, cured product thereof, and laminate comprising the cured product
EP2966144B1 (en) 2013-03-04 2017-10-25 Tokuyama Corporation Photochromic curable composition
US11401276B2 (en) 2017-07-14 2022-08-02 Tokuyama Corporation Chromene compound, curable composition comprising the compound, and optical article including a cured body of the curable composition
US10866455B2 (en) 2017-10-19 2020-12-15 Ppg Industries Ohio, Inc. Display devices including photochromic-dichroic compounds and dichroic compounds
MX2020008644A (en) 2018-02-23 2020-09-21 Tokuyama Corp Functional multilayer body and functional lens using functional multilayer body.
BR112020020189A2 (en) 2018-04-05 2021-01-05 Tokuyama Corporation PHOTOCHROMIC ADHESIVE COMPOSITION, PHOTOCHROMIC LAMINATE, AND, OPTICAL ITEM.
JPWO2019198664A1 (en) 2018-04-12 2021-04-30 株式会社トクヤマ Photochromic optical articles and their manufacturing methods
WO2019203205A1 (en) 2018-04-17 2019-10-24 株式会社トクヤマ Photochromic compound, curable composition containing said photochromic compound, and optical article
JP7152173B2 (en) * 2018-04-17 2022-10-12 株式会社トクヤマ Method for producing photochromic cured body
DE102018004790A1 (en) 2018-06-14 2019-12-19 Rodenstock Gmbh Photochromic annealed naphthopyran systems with special substituents to achieve very fast lightening speeds
CA3105467A1 (en) 2018-07-20 2020-01-23 Tokuyama Corporation Photochromic compound and curable composition containing said photochromic compound
EP3950624A1 (en) 2019-04-03 2022-02-09 Tokuyama Corporation Photochromic optical article and method for manufacturing same
KR20220084022A (en) 2019-10-17 2022-06-21 가부시끼가이샤 도꾸야마 Photochromic hydroxyurethane compound
US20230109024A1 (en) 2020-02-28 2023-04-06 Tokuyama Corporation Photochromic curable composition and photochromic optical article
KR20220150275A (en) 2020-02-28 2022-11-10 가부시키가이샤 도쿠야마 Moisture-curable polyurethane composition and laminate
US20210284778A1 (en) 2020-03-11 2021-09-16 Alcon Inc. Photochromic polydiorganosiloxane vinylic crosslinkers
EP4163270A1 (en) 2020-05-28 2023-04-12 Tokuyama Corporation Compound for optical material, curable composition, cured body, and optical article
WO2021245551A1 (en) 2020-06-02 2021-12-09 Alcon Inc. Method for making photochromic contact lenses
US20230280500A1 (en) 2020-08-06 2023-09-07 Tokuyama Corporation Photochromic compound, photochromic curable composition, cured body, lens and eyeglasses
EP4237232A1 (en) 2020-10-28 2023-09-06 Alcon Inc. Method for making photochromic contact lenses
EP4240579A1 (en) 2020-11-04 2023-09-13 Alcon Inc. Method for making photochromic contact lenses
WO2022097048A1 (en) 2020-11-04 2022-05-12 Alcon Inc. Method for making photochromic contact lenses
MX2023008270A (en) 2021-01-25 2023-07-19 Tokuyama Corp Resin composition, optical laminate, optical article, lens, and glasses.
WO2022189940A1 (en) 2021-03-08 2022-09-15 Alcon Inc. Method for making photofunctional contact lenses
EP4306318A1 (en) 2021-03-08 2024-01-17 Tokuyama Corporation Photochromic curable composition, photochromic laminate, and method for producing same
KR20230144634A (en) 2021-04-01 2023-10-16 알콘 인코포레이티드 Method for manufacturing photochromic contact lenses
WO2023209631A1 (en) 2022-04-28 2023-11-02 Alcon Inc. Method for making uv and hevl-absorbing ophthalmic lenses

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61263982A (en) * 1985-01-25 1986-11-21 Mitsubishi Chem Ind Ltd 3,3-dimethyl-spiro(indolino-2,3'-naphtho(2,1-b)-(1,4) oxazine) compound
JP2711139B2 (en) * 1989-06-07 1998-02-10 株式会社トクヤマ Chromene compound and method for producing the same
JPH0391578A (en) * 1989-09-05 1991-04-17 Toray Ind Inc Coating composition
JPH03100091A (en) * 1989-09-13 1991-04-25 Toray Ind Inc Photochromic material
US5585042A (en) * 1992-02-24 1996-12-17 Transitions Optical, Inc. Photochromic naphthopyrans
DE59304881D1 (en) * 1992-10-15 1997-02-06 Ciba Geigy Ag Polymerizable photochromic napthacenediones, polymers of these monomers, processes for their preparation and their use
US5552091A (en) * 1993-03-12 1996-09-03 Ppg Industries, Inc. Benzopyran compounds
US5466398A (en) * 1993-06-21 1995-11-14 Transitions Optical, Inc. Photochromic substituted naphthopyran compounds
US5578252A (en) * 1993-06-21 1996-11-26 Transitions Optical, Inc. Photochromic substituted naphthopyran compounds
GB9316858D0 (en) * 1993-08-13 1993-09-29 Pilkington Plc Photochromic compounds
US5458814A (en) * 1993-12-09 1995-10-17 Transitions Optical, Inc. Substituted naphthopyrans
US5651923A (en) * 1993-12-09 1997-07-29 Transitions Optical, Inc. Substituted naphthopyrans
IL115803A (en) * 1994-11-03 2000-02-17 Ppg Industries Inc Indeno-naphthopyran derivatives useful for photochromic articles
US5645767A (en) * 1994-11-03 1997-07-08 Transitions Optical, Inc. Photochromic indeno-fused naphthopyrans
JPH08176139A (en) * 1994-12-20 1996-07-09 Tokuyama Corp Chromene compound
US5658501A (en) * 1995-06-14 1997-08-19 Transitions Optical, Inc. Substituted naphthopyrans
US5658500A (en) * 1995-06-14 1997-08-19 Transitions Optical, Inc. Substituted naphthopyrans
AUPN443695A0 (en) * 1995-07-28 1995-08-17 Sola International Holdings Ltd Photochromic polymer
US5744070A (en) * 1995-12-20 1998-04-28 Transitions Optical, Inc. Photochromic substituted naphthopyran compounds
US5753146A (en) * 1996-03-29 1998-05-19 Transitions Optical, Inc. Photochromic naphthopyran compositions of neutral color
GB9706203D0 (en) * 1997-03-25 1997-05-14 James Robinson Ltd Intense colouring photochromic 2H-naphthol[1,2-b]pyrans and heterocyclic pyrans
JP3982770B2 (en) * 1997-04-30 2007-09-26 株式会社トクヤマ Chromene compounds

Also Published As

Publication number Publication date
AU758378B2 (en) 2003-03-20
EP1112264B1 (en) 2002-11-27
DE69904211D1 (en) 2003-01-09
AU5914499A (en) 2000-04-03
ES2188241T3 (en) 2003-06-16
WO2000015630A1 (en) 2000-03-23
CA2343226C (en) 2005-11-15
JP2002524559A (en) 2002-08-06
BR9913868A (en) 2002-01-15
US5961892A (en) 1999-10-05
EP1112264A1 (en) 2001-07-04
DE69904211T2 (en) 2003-07-24
JP4550281B2 (en) 2010-09-22
CO5221040A1 (en) 2002-11-28

Similar Documents

Publication Publication Date Title
CA2343226A1 (en) Polyalkoxylated naphthopyrans
CA2343310A1 (en) Polymerizable polyalkoxylated naphthopyrans
WO2001070719A3 (en) Hydroxylated/carboxylated naphthopyrans
CA2256478A1 (en) Novel photochromic indeno-fused naphthopyrans
CA2187100A1 (en) Novel substituted naphthopyrans
CA2204179A1 (en) Novel photochromic indeno-fused naphthopyrans
CA2385728A1 (en) Novel photochromic naphthopyrans
EP1642895A3 (en) Novel substituted naphthopyrans
CA2123500A1 (en) Photochromic Naphthopyran Compounds
CA2097606A1 (en) Photochromic Naphthopyrans
US5879592A (en) Water soluble photochromic compounds, compositions and optical elements comprising the compounds
US5723072A (en) Photochromic heterocyclic fused indenonaphthopyrans
US5578252A (en) Photochromic substituted naphthopyran compounds
BR0116758A (en) Naphthopyran Compound and Photochromic Article
WO2000002884A3 (en) Photochromic benzopyrano-fused naphthopyrans
CA2164949A1 (en) Photochromic Naphthopyran Compounds
MX9704662A (en) Organic photochromic materials with high refractive index, their preparation and articles formed from these materials.
DE60103847D1 (en) SUBSTITUTED PHOTOCHROMIC 2H-NAPHTHO [1,2-B] PYRANE COMPOUNDS
WO2004047674A3 (en) Oxyge-containing heterocyclic fused naphthopyrans
CA2293834A1 (en) Substituted naphthopyrans
TH40867A3 (en) Polymerized polyalcoxylate naphthopyran
TH49388A (en) New types of photochromic naphthopyran
TH17383EX (en) Naphthopyran compounds, which are replaced by photochromic types

Legal Events

Date Code Title Description
EEER Examination request