WO2014208994A1 - Composition apte à être polymérisée pour matière optique hautement réfractante, composition photochromique correspondante et procédé de préparation de matière optique hautement réfractante utilisant les compositions - Google Patents

Composition apte à être polymérisée pour matière optique hautement réfractante, composition photochromique correspondante et procédé de préparation de matière optique hautement réfractante utilisant les compositions Download PDF

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Publication number
WO2014208994A1
WO2014208994A1 PCT/KR2014/005599 KR2014005599W WO2014208994A1 WO 2014208994 A1 WO2014208994 A1 WO 2014208994A1 KR 2014005599 W KR2014005599 W KR 2014005599W WO 2014208994 A1 WO2014208994 A1 WO 2014208994A1
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WO
WIPO (PCT)
Prior art keywords
formula
optical material
high refractive
refractive optical
polymerizable composition
Prior art date
Application number
PCT/KR2014/005599
Other languages
English (en)
Korean (ko)
Inventor
장동규
노수균
김종효
Original Assignee
주식회사 케이오씨솔루션
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.)
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Publication date
Application filed by 주식회사 케이오씨솔루션 filed Critical 주식회사 케이오씨솔루션
Priority to CN201480035945.5A priority Critical patent/CN105339812A/zh
Publication of WO2014208994A1 publication Critical patent/WO2014208994A1/fr

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Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/54—Acrylic acid esters; Methacrylic acid esters
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

Definitions

  • the photochromic polymerizable composition may further include one or two or more compounds selected from the compound represented by Formula 3, the compound represented by Formula 4, the compound represented by Formula 5, and other acrylic monomers.
  • the high refractive optical material or the photochromic high refractive optical material includes optical lenses such as spectacle lenses.
  • the polymerizable composition for high refractive optical material of the present invention includes any one or more of the compound represented by Formula 1 and the compound represented by Formula 2.
  • the polymerizable composition is a compound represented by the following formula (3), a compound represented by the formula (4), a compound represented by the formula (5), diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol as another acrylic monomer Dimethacrylate.
  • n 3 ⁇ 10.
  • the polymerizable composition of the present invention may further include a compound represented by Formula 6 below.
  • the heat stabilizer can be used for all of the heat stabilizer surfaces that can be used for optical lenses such as phosphorus heat stabilizers, metal fatty acid salts, lead compounds, and organic tin compounds.
  • a triphenyl phosphite a diphenyldecyl phosphite, a diphenyl isodecyl phosphite, a phenyl didecyl phosphite, a diphenyl dodecyl phosphite, a trinoyl phenyl phosphite, a diphenyl isooctyl phosphate
  • the organotin type is, for example, dibutyltin diaurate, dibutyltin malate, dibutyltin bis (isooctyl maleate), dioctyltin malate, dibutyltin bis (monomethylmaleate), dibutyltin bis (Lauryl mercaptide), dibutyltin bis (isooxyl mercaptoacetate), monobutyltin tris (isooctyl mercaptoacetate), dimethyltinbis (isooctyl mercaptoacetate), methyltin tris (isooctylmer Captoacetate), dioctyl tin bis (isooctyl mercaptoacetate), dibutyl tin bis (2-mercaptoethyl laurate), monobutyl tin tris (2- mercapto ethyrate), dimethyl tin bis (2- Mercaptoethylate
  • the heat stabilizer may preferably be included in the composition at 0.01 to 5% by weight.
  • the thermal stabilizer is used at less than 0.01% by weight, the yellowing inhibitory effect is weak, and when the thermal stabilizer is used at more than 5% by weight, the polymerization failure rate during curing is high and the thermal stability of the cured product is lowered.
  • the polymerizable composition of the present invention may further include organic dyes, inorganic pigments, colorants, antioxidants, light stabilizers, and the like as in the conventional polymerizable compositions.
  • Photochromic compounds are well known, including inorganic compounds such as silver halides, spiropyrans, spiroxazines, chromenes, fulguides, azos, and fulgimides.
  • Organic compounds such as a diaryl pietene type
  • all known photochromic compounds may be used, and among them, appropriate ones may be selected in consideration of colors and the like.
  • Reversacol Platinate Purple (Spiroxazine) (manufactured by James Robinson), Reversacol Sea Green (Spiropyran) (manufactured by James Robinson), Reversacol Solar Yellow (Chromene) (manufactured by James Robinson), Reversacol Berry Red ( Spiroxazine) (manufactured by James Robinson), benzopyran, naphthopyran (naphtho [1,2b], naphtho [2,1-b]), spiro-9-fluoreno [1,2-b] pyran, Phenantropin, quinopy, indeno-fused naphthopyrans, benzoxazines, naphthoxazines, spiro (indolin) pyridobenzoxazines and the like can be used.
  • (photochromic) polymerizable composition is defined as referring to both the polymerizable composition for high refractive optical material and the polymerizable composition for photochromic high refractive optical material.
  • (Photochromic) high refractive optical material is defined to refer to a high refractive optical material and a photochromic high refractive optical material together.
  • the (photochromic) high refractive optical material obtained according to the present invention can be used in various applications such as optical lenses including spectacle lenses, as well as prismatic lenses, prism film coating agents, LED lenses, automotive headlights, and the like.
  • a fluorene-based acrylic resin having an average molecular weight of 561 g was used, and the structural formula is shown in Chemical Formula 12 below.
  • a compound having an average molecular weight of 308 g was used by introducing acrylic acid into a polyethyleneglycol having a homogeneous molecular weight of 200 g, and the structural formula is shown in Formula 13 below.
  • the prepared polymerizable composition was stirred for 1 hour, degassed under reduced pressure for 10 minutes, filtered, and then poured into a glass mold assembled with a polyester adhesive tape.
  • component (I) 60 g of component (I), 8 g of component (III), 13 g of component (IV), and 5 g of component (V) of the fluorene epoxy acrylate compound were 14 g of divinylbenzene and 0.4 alpha-methylstyrene dimer. g and 0.03 g of a photochromic coloring agent manufactured by JAMES ROBINSON were added, and the resultant was stirred for about 30 minutes.
  • Example 4 was prepared for each composition and the optical lens according to the proportion described in Table 1, without the photochromic coloring agent in the same manner as the experiment with the physical properties, the results are shown in Table 1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Eyeglasses (AREA)

Abstract

La présente invention concerne une composition apte à être polymérisée pour matière optique hautement réfractante, une composition photochromique de celle-ci et un procédé de préparation de matière optique hautement réfractante utilisant les compositions. La présente invention porte sur une composition apte à être polymérisée pour une matière optique hautement réfractante, la composition apte à être polymérisée contenant au moins l'un de composés représentés par les formules chimiques 1 et 2, et porte sur une composition photochromique contenant en outre un composé photochromique en plus de la composition apte à être polymérisée. Selon la présente invention, une matière optique à base d'acrylate de fluorène peut être obtenue, laquelle présente une performance photochromique et des caractéristiques optiques excellentes tout en étant hautement réfractante.
PCT/KR2014/005599 2013-06-24 2014-06-24 Composition apte à être polymérisée pour matière optique hautement réfractante, composition photochromique correspondante et procédé de préparation de matière optique hautement réfractante utilisant les compositions WO2014208994A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201480035945.5A CN105339812A (zh) 2013-06-24 2014-06-24 利用高折射光学材料用聚合性组合物及其光致变色组合物的高折射光学材料的制备方法

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20130072696 2013-06-24
KR10-2013-0072696 2013-06-24
KR20130074067 2013-06-26
KR10-2013-0074067 2013-06-26

Publications (1)

Publication Number Publication Date
WO2014208994A1 true WO2014208994A1 (fr) 2014-12-31

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PCT/KR2014/005599 WO2014208994A1 (fr) 2013-06-24 2014-06-24 Composition apte à être polymérisée pour matière optique hautement réfractante, composition photochromique correspondante et procédé de préparation de matière optique hautement réfractante utilisant les compositions

Country Status (3)

Country Link
KR (1) KR20150000842A (fr)
CN (1) CN105339812A (fr)
WO (1) WO2014208994A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20180039099A (ko) 2015-09-16 2018-04-17 미쯔이가가꾸가부시끼가이샤 광학 재료용 중합성 조성물, 당해 조성물로부터 얻어지는 광학 재료 및 플라스틱 렌즈
WO2018194262A1 (fr) * 2017-04-17 2018-10-25 삼성에스디아이 주식회사 Film optique d'amélioration du rapport de contraste, plaque polarisante le comprenant et appareil d'affichage à cristaux liquides le comprenant
KR20180116739A (ko) * 2017-04-17 2018-10-25 삼성에스디아이 주식회사 명암비 개선 광학 필름, 이를 포함하는 편광판 및 이를 포함하는 액정표시장치
KR20190006820A (ko) * 2017-07-11 2019-01-21 삼성에스디아이 주식회사 명암비 개선 광학필름, 이를 포함하는 편광판 및 이를 포함하는 액정표시장치
WO2019156143A1 (fr) 2018-02-09 2019-08-15 三井化学株式会社 Verre et procédé de fabrication de verre
WO2022045324A1 (fr) 2020-08-31 2022-03-03 三井化学株式会社 Composition polymérisable pour matériaux optiques et verre photochromique

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102054275B1 (ko) * 2017-01-04 2019-12-10 삼성에스디아이 주식회사 감광성 수지 조성물, 이를 이용한 감광성 수지막 및 디스플레이 장치
CN113845619A (zh) * 2021-09-30 2021-12-28 山东鲁源化工科技有限公司 一种高折射率变色单体及其制备方法和应用

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KR20020017065A (ko) * 2000-08-28 2002-03-07 김충섭 광변색 수지조성물
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KR20080075540A (ko) * 2005-12-02 2008-08-18 미쓰이 가가쿠 가부시키가이샤 단층막 및 이것으로 이루어지는 친수성 재료
JP2008290294A (ja) * 2007-05-23 2008-12-04 Osaka Gas Co Ltd 透明樹脂成形体及びその製造方法
US20090264610A1 (en) * 2006-05-05 2009-10-22 Japan Science And Technology Agency Novel Copolymer of Methacrylic Ester, Composition, Optical Element and Electric Member

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BR9609574A (pt) * 1995-07-12 1999-03-02 Corning Inc Novos materiais orgânicos fotocrômicos
US8809413B2 (en) * 2011-06-29 2014-08-19 Chau Ha Ultraviolet radiation-curable high refractive index optically clear resins

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KR100506300B1 (ko) * 1994-09-30 2005-11-16 시그넷 아모라이트, 인코포레이티드 폴리에스테르수지계,광학균일도및/또는착색성이우수한고굴절안경렌즈
KR20020017065A (ko) * 2000-08-28 2002-03-07 김충섭 광변색 수지조성물
KR20080075540A (ko) * 2005-12-02 2008-08-18 미쓰이 가가쿠 가부시키가이샤 단층막 및 이것으로 이루어지는 친수성 재료
US20090264610A1 (en) * 2006-05-05 2009-10-22 Japan Science And Technology Agency Novel Copolymer of Methacrylic Ester, Composition, Optical Element and Electric Member
JP2008290294A (ja) * 2007-05-23 2008-12-04 Osaka Gas Co Ltd 透明樹脂成形体及びその製造方法

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20180039099A (ko) 2015-09-16 2018-04-17 미쯔이가가꾸가부시끼가이샤 광학 재료용 중합성 조성물, 당해 조성물로부터 얻어지는 광학 재료 및 플라스틱 렌즈
US10921489B2 (en) 2015-09-16 2021-02-16 Mitsui Chemicals, Inc. Polymerizable composition for optical material, optical material obtained from the composition, and plastic lens
WO2018194262A1 (fr) * 2017-04-17 2018-10-25 삼성에스디아이 주식회사 Film optique d'amélioration du rapport de contraste, plaque polarisante le comprenant et appareil d'affichage à cristaux liquides le comprenant
KR20180116739A (ko) * 2017-04-17 2018-10-25 삼성에스디아이 주식회사 명암비 개선 광학 필름, 이를 포함하는 편광판 및 이를 포함하는 액정표시장치
KR102184231B1 (ko) * 2017-04-17 2020-11-27 삼성에스디아이 주식회사 명암비 개선 광학 필름, 이를 포함하는 편광판 및 이를 포함하는 액정표시장치
KR20190006820A (ko) * 2017-07-11 2019-01-21 삼성에스디아이 주식회사 명암비 개선 광학필름, 이를 포함하는 편광판 및 이를 포함하는 액정표시장치
KR102063203B1 (ko) 2017-07-11 2020-01-07 삼성에스디아이 주식회사 명암비 개선 광학필름, 이를 포함하는 편광판 및 이를 포함하는 액정표시장치
WO2019156143A1 (fr) 2018-02-09 2019-08-15 三井化学株式会社 Verre et procédé de fabrication de verre
WO2022045324A1 (fr) 2020-08-31 2022-03-03 三井化学株式会社 Composition polymérisable pour matériaux optiques et verre photochromique

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Publication number Publication date
KR20150000842A (ko) 2015-01-05
CN105339812A (zh) 2016-02-17

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