WO2004011964A1 - Lentilles de contact photochromiques et procede de fabrication associe - Google Patents

Lentilles de contact photochromiques et procede de fabrication associe Download PDF

Info

Publication number
WO2004011964A1
WO2004011964A1 PCT/KR2002/002249 KR0202249W WO2004011964A1 WO 2004011964 A1 WO2004011964 A1 WO 2004011964A1 KR 0202249 W KR0202249 W KR 0202249W WO 2004011964 A1 WO2004011964 A1 WO 2004011964A1
Authority
WO
WIPO (PCT)
Prior art keywords
contact lens
coating composition
color
photochromic
compound
Prior art date
Application number
PCT/KR2002/002249
Other languages
English (en)
Inventor
Jin-Wook Ha
Jin-Heon Ha
Jee-Nyu Hong
Seung-Hyun Cho
Original Assignee
Yujintech21 Co., Ltd.
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
Priority claimed from KR1020020044787A external-priority patent/KR20040011702A/ko
Priority claimed from KR1020020044788A external-priority patent/KR20040011703A/ko
Application filed by Yujintech21 Co., Ltd. filed Critical Yujintech21 Co., Ltd.
Priority to AU2002356463A priority Critical patent/AU2002356463A1/en
Publication of WO2004011964A1 publication Critical patent/WO2004011964A1/fr

Links

Classifications

    • 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

Definitions

  • the present invention relates, in general, to a photochromic contact lens and a method of producing the same and, in particular, to a photochromic contact lens having a short variable time, and a method of producing the same.
  • the variable time is defined as a time required for a lens to return to its original color when removed from the influence of sunlight or ultraviolet light after being discolored by exposure to the sunlight or ultraviolet light.
  • aTphotochromic lens has a light color approaching to colorlessness indoors, but attains a dark depth of color outdoors when exposed to ultraviolet light or visible light having short wavelength.
  • the photochromic lens is also called a 'Coming lens', originating from Coming Co. of United States of America, which initially produced it. Because the photochromic lens includes fine crystals such as silver chloride (AgCl), silver bromide (AgBr), and silver iodide (Agl) dispersed in a glass or plastic lens, the depth of color is changed according to the irradiation amount of ultraviolet light.
  • the photochromic lens is defined as a lens making a repetition of coloring when being irradiated by ultraviolet light, and which becomes transparent when being not exposed to ultraviolet light.
  • the photochromic lens blocks ultraviolet light of sunlight to reduce eye strain and protect eyes from injurious ultraviolet light (UV-B) known for inducing cataracts, and since it filters 70 to 80 % of sunlight, it can be applied to various applications.
  • the photochromic lens may act as sunglasses in summer when a great quantity of sunlight is irradiated, or outdoors.
  • various photovariable color compounds are used to produce photochromic lenses.
  • the term photovariable color compound denotes a compound, being reversibly changed in terms of its color, discolored when being irradiated by ultraviolet light such as sunlight or mercury lamp light, and returns to its original color when not affected by ultraviolet light or stored in a dark room.
  • a representative compound is a spirooxazine compound disclosed in U.S. Pat. Nos. 4,215,010 and 4,342,668.
  • pyran derivatives such as spiropyran or naphtopyran, fulgide, acridone, and naphthacene quinone are known in the art.
  • the present inventors developed a photochromic contact lens with short variable time and good surface strength and ultraviolet ray filtering effect without an undesirable haze phenomenon by dissolving spiropyran based compounds, spirooxazin based compounds, or a mixture thereof in toluene in a predetermined mixing ratio, then incorporating an acryl based binder to produce the resulting solution, coating the resulting solution on a contact lens, and heat-curing the coated lens.
  • a coating composition for a photochromic contact lens comprising 1.5 to 5 wt% spiropyran compound defined by the following Formula I, or spirooxazine compound defined by the following Formula II, or a mixture thereof, 60 to 65 wt% toluene, and an acryl based binder to make 100 wt% of the coating composition is provided:
  • R is alkyl with 1 to 30 carbon atoms
  • Rl is alkyl, alkenyl, or alkoxy with 1 to 10 carbon atoms, or substituted or non-substituted phenyl,
  • R2 to R5 are independently hydrogen atom, halogen, cyano, nitro, or alkyl or alkoxy with 1 to 6 carbon atoms, and
  • X is hydroxy, glycidoxy, amine, or dichlorotrioxazinoxy.
  • a photochromic contact lens coated with a coating composition comprising 1.5 to 5 wt% spiropyran compound defined by the Formula I, or spirooxazine compound defined by the Formula II, or a mixture thereof, 60 to 65 wt% toluene, and an acryl based binder to make 100 wt% of the coating composition.
  • a method of producing a photochromic contact lens comprising coating a surface of the photochromic contact lens with a coating composition including 1.5 to 5 wt% spiropyran compound defined by the Formula I, or spirooxazine compound defined by the Formula II, or a mixture thereof, 60 to 65 wt% toluene, and an acryl based binder to make 100 wt% of the coating composition; and heat-curing the resulting structure.
  • Fig. 1 is a graph showing an UV/Vis spectrum for a photochromic contact lens of the present invention, in which transmittance variation is plotted according to wavelength of light irradiated into the photochromic contact lens. Best Mode for Carrying Out the Invention
  • Contact lenses are classified into hard contact lenses and soft contact lenses according to materials constituting the contact lens.
  • hard contact lenses include a RGP (rigid gas permeable) lens, through which oxygen can be readily penetrated, and a PMMA (polymethylmethacrylate) lens.
  • PMMA polymethylmethacrylate
  • the soft contact lenses a daily-wearable lens, an extended-wearable lens, and a disposable lens may be exemplified.
  • a coating composition of the present invention is applied to all the above-described contact lenses.
  • a spiropyran compound of Formula I a spirooxazin compound of Formula II, or a mixture thereof is used as a photovariable color compound.
  • the photovariable color compound is well known in the art, and for example, the spiropyran compound of Formula I is disclosed in US Pat. No.
  • the spiropyran compound of Formula I and the spirooxazin compound of Formula II may be used as the photovariable color compound alone or in a mixed form. It may be properly selected according to the desired color whether to use the above compounds alone or in a mixed form, depending on the type of the photovariable color compound.
  • the spiropyran based compound and spirooxazin based compound absorb ultraviolet light from the sunlight and emit as violet, yellow, green, brown, red, or blue in color, but becomes transparent when it is not exposed to UV.
  • Photovariable color compounds of the present invention can be mixed together while being dissolved in toluene to produce a solution having a different color from the original colors of the components. For example, if a yellow liquid is mixed with a blue liquid to produce a coating liquid composition, a surface of the contact lens coated with the coating liquid composition will be green.
  • an acryl based binder is useful as a binder of the present invention, and the binder may be selected from the group consisting of an organic binder, an inorganic binder, or a mixture thereof.
  • the binder can be obtained as a commercial binder, or produced according to a conventional binder producing method.
  • a solvent for dissolving the photovariable color compound is an organic solvent such as hexane, xylene, toluene, methylene chloride, ethyl acetate, and butyl acetate.
  • the spiropyran compound of Formula I, or the spirooxazin compound of Formula II, or a mixture thereof is most soluble in toluene and methylene chloride.
  • toluene is most preferably used as the solvent in the present invention.
  • the coating composition for the photochromic contact lens comprises 1.5 to 5 wt% spiropyran compound defined by Formula I, or spirooxazine compound defined by Formula II, or a mixture thereof, 60 to 65 wt% toluene, and an acryl based binder to make 100 wt% of the coating composition.
  • an acryl based binder content is undesirably low, a coated layer is not completely attached to a surface of the contact lens, thereby reducing adhesion and hardness.
  • the binder content is excessively high, viscosity is increased and the coated layer becomes thick, thereby making the surface of the coated layer uneven.
  • the photovariable color compound is additionally added.
  • toluene is added to the photovariable color compound in such an amount that the concentration of the photovariable color compound in toluene is less than the maximum soluble amount
  • depth of the color of the coated layer is lowered.
  • toluene is mixed with the photovariable color compound in such an amount that the concentration of the photovariable color compound in toluene is more than the maximum soluble amount, the photovariable color compound is not completely dissolved in toluene and will be precipitated on the bottom.
  • the composition including the photovariable color compound of Formula I and/or Formula II, toluene, and the acryl based binder may be coated on the contact lens by various coating processes such as a manually coating process, a spin coating process, a dip coating process, or a spray coating process.
  • the contact lens is coated with the coating composition of the present invention, and heat-cured to produce a photochromic contact lens.
  • the photovariable color compound of the present invention has poor heat resistance. Therefore, if the curing temperature is too high, the contact lens is not able to fulfill its function of changing color.
  • the curing temperature is 30 to 80 ° C .
  • the coating composition obtained from Example 1 was spin-coated on a surface of a RGP contact lens, and heat-cured at 80 ° C to produce the photochromic contact lens.
  • the coating composition obtained from Example 2 was dip-coated on a surface of a RGP contact lens, and heat-cured at 80 ° C to produce the photochromic contact lens.
  • the photochromic contact lens obtained from Example 3 was exposed to sunlight. Then, the exposed photochromic contact lens turned brown. The brown photochromic contact lens lost its color and became transparent within 1 min after the lens was moved to indoors where exposure to sunlight was blocked.
  • the photochromic contact lens obtained from example 3 was measured in terms of transmissivity of ultraviolet light using a UV/Vis spectrum. The results are described in FIG. 1. From the results of FIG. 1, it can be seen that the photochromic contact lens of the present invention has a 99 % or higher ultraviolet ray blocking ratio.
  • the photochromic contact lens obtained from example 3 was measured in terms of adhesive strength according to the KS D 6711-92 test procedure. The results were 100/100. This proves that the photochromic contact lens according to the present invention has excellent adhesive strength.
  • a photochromic contact lens according to the present invention is advantageous in that its variable time is short, an undesirable haze phenomenon does not occur, and it has good adhesion of a coating composition to a contact lens and ultraviolet ray filtering effect.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Eyeglasses (AREA)
  • Optical Filters (AREA)

Abstract

L'invention concerne une composition de revêtement pour des lentilles de contact photochromiques ainsi que les lentilles de contact photochromiques revêtues de cette composition. Cette composition de revêtement contient un composé couleur photovariable de spiropyrane et/ou un composé couleur photovariable de spirooxazine dissous dans du toluène, ainsi qu'un liant acrylique. Les lentilles de contact photochromiques revêtues de cette composition de revêtement possèdent les avantages suivants : temps variable court, bonne adhérence de la composition de revêtement sur les lentilles de contact et effet anti-UV sans phénomène de voile indésirable.
PCT/KR2002/002249 2002-07-30 2002-11-29 Lentilles de contact photochromiques et procede de fabrication associe WO2004011964A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002356463A AU2002356463A1 (en) 2002-07-30 2002-11-29 Photochromic contact lens and method for preparation thereof

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR1020020044787A KR20040011702A (ko) 2002-07-30 2002-07-30 조광콘택트렌즈용 코팅액 조성물
KR2002/44787 2002-07-30
KR1020020044788A KR20040011703A (ko) 2002-07-30 2002-07-30 조광렌즈의 제조방법
KR2002/44788 2002-07-30

Publications (1)

Publication Number Publication Date
WO2004011964A1 true WO2004011964A1 (fr) 2004-02-05

Family

ID=31190422

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2002/002249 WO2004011964A1 (fr) 2002-07-30 2002-11-29 Lentilles de contact photochromiques et procede de fabrication associe

Country Status (2)

Country Link
AU (1) AU2002356463A1 (fr)
WO (1) WO2004011964A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8211338B2 (en) 2003-07-01 2012-07-03 Transitions Optical, Inc Photochromic compounds
US8518546B2 (en) 2003-07-01 2013-08-27 Transitions Optical, Inc. Photochromic compounds and compositions
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
CN112731685A (zh) * 2021-01-29 2021-04-30 甘肃天后光学科技有限公司 一种光致变色软性角膜接触镜及其制备方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4756973A (en) * 1985-07-09 1988-07-12 Kureha Kagaku Kogyo Kabushiki Kaisha Photochromic lens
US4929693A (en) * 1987-02-02 1990-05-29 Toray Industries, Inc. Photochromic compound
US4994208A (en) * 1989-04-18 1991-02-19 Ppg Industries, Inc. Photochromic polymeric article
US5581090A (en) * 1995-10-25 1996-12-03 Solartech Enterprises, Llc Photochromic ultraviolet detector
US5833885A (en) * 1993-08-13 1998-11-10 Pilkington Plc Photochromic compounds
US6194511B1 (en) * 1998-03-02 2001-02-27 Tokuyama Corporation Photochromic curable composition

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4756973A (en) * 1985-07-09 1988-07-12 Kureha Kagaku Kogyo Kabushiki Kaisha Photochromic lens
US4929693A (en) * 1987-02-02 1990-05-29 Toray Industries, Inc. Photochromic compound
US5166345A (en) * 1987-02-02 1992-11-24 Toray Industries, Inc. Photochromic compound
US4994208A (en) * 1989-04-18 1991-02-19 Ppg Industries, Inc. Photochromic polymeric article
US5833885A (en) * 1993-08-13 1998-11-10 Pilkington Plc Photochromic compounds
US5581090A (en) * 1995-10-25 1996-12-03 Solartech Enterprises, Llc Photochromic ultraviolet detector
US6194511B1 (en) * 1998-03-02 2001-02-27 Tokuyama Corporation Photochromic curable composition

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8211338B2 (en) 2003-07-01 2012-07-03 Transitions Optical, Inc Photochromic compounds
US8518546B2 (en) 2003-07-01 2013-08-27 Transitions Optical, Inc. Photochromic compounds and compositions
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
US8705160B2 (en) 2003-07-01 2014-04-22 Transitions Optical, Inc. Photochromic compounds
US9309455B2 (en) 2003-07-01 2016-04-12 Transitions Optical, Inc. Indeno-fused ring compounds
US10000472B2 (en) 2003-07-01 2018-06-19 Transitions Optical, Inc. Photochromic compounds
US10005763B2 (en) 2003-07-01 2018-06-26 Transitions Optical, Inc. Photochromic compounds
US10501446B2 (en) 2003-07-01 2019-12-10 Transitions Optical, Inc. Photochromic compounds
US10532998B2 (en) 2003-07-01 2020-01-14 Transitions Optical, Inc. Photochromic compounds
US10532997B2 (en) 2003-07-01 2020-01-14 Transitions Optical, Inc. Photochromic compounds
CN112731685A (zh) * 2021-01-29 2021-04-30 甘肃天后光学科技有限公司 一种光致变色软性角膜接触镜及其制备方法

Also Published As

Publication number Publication date
AU2002356463A1 (en) 2004-02-16

Similar Documents

Publication Publication Date Title
US7320826B2 (en) Photochromic articles with reduced temperature dependency and methods for preparation
US4968454A (en) Variable-light transmittance article and method for preparing same
AU744068B2 (en) Alkoxyacrylamide photochromic coating composition and photochromic articles
US9017820B2 (en) Laminated glass lens for spectacles
EP3345052B1 (fr) Articles photochromiques multicouche
US5021196A (en) Method for preparing variable-light transmittance article
JP2005500925A (ja) 光可逆性変色度数偏光サングラスレンズ及び製造方法
CN109648956B (zh) 光致变色材料及其制备方法、应用
JP2014032273A (ja) フォトクロミックレンズ
US20110189462A1 (en) Encapsulated photochromic dyes
WO2019238648A1 (fr) Lentilles à couleur équilibrée présentant une transmittance de lumière bleue réduite
JPH11513055A (ja) ホトクロミックな用途のための高分子材料
EP1540382A1 (fr) Lentille photochrome en plastique et procede de preparation associe
WO2004011964A1 (fr) Lentilles de contact photochromiques et procede de fabrication associe
JPS6321605A (ja) 調光作用を有する偏光性樹脂製光学部材
JPH0396901A (ja) 調光作用を有する偏光性樹脂製光学部材
KR20040011703A (ko) 조광렌즈의 제조방법
KR20040011702A (ko) 조광콘택트렌즈용 코팅액 조성물
KR20040011701A (ko) 플라스틱 조광렌즈용 코팅액 조성물
CN105353436B (zh) 一种镜片防蓝光膜
WO2019238650A1 (fr) Lentille à accentuation des couleurs
JP2023150015A (ja) 光学物品の製造方法
JPH0756521B2 (ja) 耐溶剤性および耐摩耗性に優れた調光レンズおよびその製造方法
CH579783A5 (en) photochromic sunglasses - stable and efficient, contg a photochromic cpd in an epoxy resin
DE2306019A1 (de) Photochrome sonnenschutzglaeser

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SD SE SG SI SK SL TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR IE IT LU MC NL PT SE SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: JP

WWW Wipo information: withdrawn in national office

Country of ref document: JP