EP0944471A4 - Preforme pour lentilles optiques - Google Patents

Preforme pour lentilles optiques

Info

Publication number
EP0944471A4
EP0944471A4 EP97908998A EP97908998A EP0944471A4 EP 0944471 A4 EP0944471 A4 EP 0944471A4 EP 97908998 A EP97908998 A EP 97908998A EP 97908998 A EP97908998 A EP 97908998A EP 0944471 A4 EP0944471 A4 EP 0944471A4
Authority
EP
European Patent Office
Prior art keywords
optical
paπially
layer
polymeric layer
hardened
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.)
Withdrawn
Application number
EP97908998A
Other languages
German (de)
English (en)
Other versions
EP0944471A1 (fr
Inventor
Amitava Gupta
Ronald D Blum
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.)
INNOTECH Inc
INNOTECH Inc
Original Assignee
INNOTECH Inc
INNOTECH 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 INNOTECH Inc, INNOTECH Inc filed Critical INNOTECH Inc
Publication of EP0944471A1 publication Critical patent/EP0944471A1/fr
Publication of EP0944471A4 publication Critical patent/EP0944471A4/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
    • B29D11/00—Producing optical elements, e.g. lenses or prisms
    • B29D11/0073—Optical laminates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29L—INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
    • B29L2011/00—Optical elements, e.g. lenses, prisms
    • B29L2011/0016—Lenses
    • B29L2011/0033—Multifocal lenses

Definitions

  • the present invention relates generally to optical preforms and, more particularly, to optical preforms that have an adjacent layer of partially hardened resin that can be used to produce an optical product.
  • Optical elements such as ophthalmic lenses are commonly either cast directly from a polymerizable resin or ground to specification from a semi ⁇ finished blank which has been previously cast from a polymerizable resin.
  • Optical elements may also be built up as a multilayer assembly using techniques such as plasma polymerization, spin casting, sequential casting or photolithography. In all cases, the optical element is created to meet certain optical specifications.
  • multifocal ophthalmic lenses are generally manufactured in two steps: 1) molding a semi-finished blank, and 2) grinding the unfinished surface to form the final prescription.
  • This method of generating ophthalmic lenses is time consuming, and expensive.
  • Blum US Patent 5,219,497 has developed a method of casting a thin layer of polymerizable resin on the outer surface of a single vision lens or a semi-finished blank which provides an add power zone on the lens.
  • the distance prescription is incorporated in the single vision lens, while the resin layer cast over the single vision lens preserves the distance correction provided by the lens blank over much of the lens area.
  • Greshes (US Patent 4.190.621) describes a casting process which involves supporting the lens preform on a fixture and placing a mold of matching curvature underneath the lens, with an intervening liquid resin layer between the mold and the lens preform.
  • Verhoeven (US Patent 4,623,496) discloses a method of casting a thin layer of resin over an optical preform of spherical geometry. Ito (US Patent 4 536,267) discloses photopolymerizable resins incorporating a photoinitiator and a thermal polymerization initiator.
  • Toh discloses a photopolymerizable resin for fabrication of whole lenses.
  • a liquid resin in lens casting can result in inconveniences, such as those associated with transportation and delivery of a reactive fluid.
  • shrinkage associated with curing may cause optical distortions to develop in the lens.
  • the present invention solves these and other inconveniences of the prior art by providing an optical preform composed of an optical article, such as a single vision lens, with an adjacent layer of a partially hardened resin.
  • the adjacent layer can be conformed to a mold and further hardened (e.g. cross-linked) to modify the optical properties of the preform as desired.
  • the adjacent layer may be placed on any (e.g. , anterior or posterior) surface of the optical article.
  • the partially hardened resin layer can be initially placed on the optical article prior to positioning the optical article against a mold.
  • the partially hardened resin layer can be initially placed on the surface of the mold prior to positioning the optical article against the mold.
  • the mold surface supporting the partially hardened resin layer may be either generally convex or concave.
  • Such a preform can be manufactured in bulk and stocked at the dispensing site. It is readily convened to a number of optical products such as a finished spherical or aspheric, toric, single vision, bifocal, multifocal or progressive semi-finished blank, ophthalmic lens or lens preform.
  • Other optical products may include molds, intraocular lenses, contact lenses or other optical elements such as those needed for optical signal processing or optical computing.
  • a mold may be used to define the final surface configuration of the partially hardened resin layer, the surface may also be configured by a number of known means that do not require a mold, such as spinning, spraying, dipping and photolithography.
  • any thermal process may be used to heat the partially hardened polymeric layer so that the layer will soften and flow during spinning to a desired surface configuration.
  • the photocuring process may begin. This photocuring process will continue while the partially hardened polymeric layer continues to be spun. This photocuring further hardens the polymeric layer into the final shape.
  • this process can be performed in oxygen or in oxygen-free environments, such as in the presence of nitrogen.
  • the photocuring step can use visible or ultraviolet light or both.
  • FIG. 1 is a cross-section of a mold and an optical preform in accordance with the present invention.
  • FIG. 2 is a cross-section of an optical article and an adjacent mold according to the present invention.
  • FIG. 3 is a cross-section of a partially hardened layer on an optical article according to the present invention.
  • FIG. 4 is a cross-section of a partially hardened layer disposed on the concave surface of a mold according to the present invention.
  • FIG. 5 is a cross-section of a partially hardened layer disposed on the convex surface of a mold according to the present invention.
  • an embodiment of the present invention for making an optical preform without the use of liquid polymerizable resin uses a preform comprising an optical article 10. such as a single vision lens, adhesively bonded to an adjacent, partially hardened polymeric layer 20 on a surface of the lens.
  • the polymeric layer 20 may be over-coated with additional adjacent layers that are designed to provide specific optical functions and/or scratch resistance.
  • the polymeric layer may be initially placed on the surface of the optical article, it is also possible to place the polymeric layer initially on the surface of the mold.
  • the optical preform having the attached polymeric layer is placed in contact with a mold 30 incorporating the optical geometry desired in the finished lens, whereupon it is subjected to light, heat or a combination of both, so as to complete the curing of the adjacent layer 20 or layers and form the finished lens.
  • the layer 20 is conformed to the mold 30, for example, by heat, pressure or both.
  • the mold/polymeric layer assemblage When the partially hardened polymeric layer is initially placed on the mold surface, the mold/polymeric layer assemblage is then placed in contact with the optical article surface and the polymeric layer is fully cured and bonded to the surface of the optical article prior to removal of the mold. It is thus possible to mass produce, at a low cost, finished lenses of complex geometry through the use of optical preforms composed of an optical article 10, incorporating certain elements of the final optical geometry, and a polymeric layer 20, wherein a mold 30 or other forming method provides the remaining elements of the final geometry from the polymeric layer 20.
  • an aspheric lens corrected for spherical aberration can be made by using an optical preform comprising a spherical optical article 10 with an adjacent layer 20, and an aspheric mold of matching base curve.
  • the optical article 10 can be, for example, a single vision lens of spherical, aspheric, or toric geometry, a bifocal, multifocal or progressive lens, and so forth.
  • the mold 30 can be used to provide spherical, aspheric or toric corrections, bifocal, multifocal or progressive zones, and so forth.
  • the only limitation of this approach to complex optical geometries is that the desired geometry can be decomposed into one or more simpler geometrical elements, using the method of linear superposition.
  • Single vision or other lenses made of glass, plastics such as CR-39TM, polycarbonate of bisphenol A, or other polymers may be used as optical articles in the fabrication of optical preforms.
  • the optical article may be hard, or soft and pliable.
  • the refractive index of the lens may be selected from a wide range, e.g. , 1.42 to 1.70 for typical ophthalmic lenses.
  • Semi ⁇ finished blanks may also be used as optical articles in the optical preform.
  • Other articles, such as Fresnel lenses, optical reflectors, prisms, and so forth, may also be treated and modified in this fashion to form an optical product.
  • the optical article can be made of plastic, metal or glass or a combination thereof.
  • the adjacent polymeric layer or layers may be formed, for example, by polymerizing a mixture of acrylates, methacrylates, styrenics or allylics. This curing process may be accomplished thermally, photochemically or both.
  • the selection of the constituent monomers preferably depends upon the chemical composition of the convex surface of the single vision lens and its refractive index.
  • the adjacent layer is preferably formulated so that, upon completion of cure, the adjacent layer forms a strong and durable bond to the optical a ⁇ icle.
  • the adjacent layer is also preferably formulated to develop a refractive index of the adjacent layer in the fully cured state that is matched to within 0.05 units, and more preferably within 0.03 units, of the refractive index of the single optical article.
  • the polymerization may be carried out by using thermal polymerization initiators, photopolymerization initiators, or a mixture of both.
  • the polymerization is carried out until the glass transition temperature reaches a range of 20-40 °C, more preferably 25-35 °C.
  • the cross-link density at this stage is preferably less than 10 "4 moles/liter.
  • This polymeric layer is then preferably imbibed with a multifunctional monomer and an additional amount of polymerization initiator.
  • the initiator allows further curing to take place once the optical preform is placed in contact with the mold surface, and the multifunctional monomer enhances the cross-link density of the layer.
  • Other variations are contemplated, such as the use of photo initiators that cure at different wavelengths.
  • the optical preform is fabricated by forming the adjacent layer on one or more surfaces of the optical article.
  • a layer of the liquid formulation may be applied to the optical article, by dipping it into a bath of the monomer formulation, by spin coating a uniform layer of the liquid formulation on the surface of the optical article, and so forth.
  • the optical article 10 may be placed in an adjacent layer mold 40 and the cavity 50 formed between the optical article 10 and the adjacent layer mold 40 filled with the monomer formulation.
  • the layer of the liquid formulation may then be partially cured as described above.
  • the curing process may be accomplished thermally, photochemically or both.
  • the process of applying and curing the liquid layer may be repeated, either using the same formulation in order to build up thickness or with a different formulation to vary properties.
  • FIG. 1 illustrates an embodiment in which a partially hardened resin layer is disposed on the convex surface of an optical article prior to positioning of the layer/article assembly against a mold surface
  • the resin layer 20 may also be disposed on a concave surface of the optical a ⁇ icle 10, as illustrated in FIG. 3.
  • the partially hardened resin layer 10 may be initially disposed on either the concave or convex surfaces, respectively, of the mold 30 prior to positioning the optical a ⁇ icle 10 against the mold/layer assembly.
  • the mold used for completion of curing the optical preform may be made of plastic, glass, glass coated with metal, metal alone and so fo ⁇ h. and may be either reusable or disposable. While it is not always required, the base curve of the mold preferably matches the front curve of the optical preform, allowing for the shrinkage of the adjacent layer that accompanies the completion of the cure process.
  • most of the shrinkage accompanying the polymerization reaction is incurred during the formation of the adjacent layer.
  • a typical mixture of mono- and bi-functional acrylates may undergo a polymerization shrinkage of 12-18% upon completion of cure. However, up to 70% of this overall shrinkage occurs during the initial polymerization reaction that leads to the formation of the adjacent layer 20. The rest of the shrinkage, associated with the cross-linking reaction, occurs in the mold 30.
  • the radiation may be delivered through the mold 30. If the mold is made of metal or some other material opaque to the actinic radiation, then the radiation is delivered through the optical a ⁇ icle 10. In some cases, the actinic radiation may be delivered through both the mold 30 and the optical a ⁇ icle 10.
  • An optical preform includes an optical a ⁇ icle consisting of a single vision lens cast from CR-39TM monomer and an adjacent layer of a pa ⁇ ially cured polymeric layer adhesively bonded to the convex surface of the CR-39TM lens body
  • This polymeric layer incorporates unreacted cross-linkers and additional unreacted photo initiator required for completion of the cure
  • the polymeric layer is cured to a level such that the material is elastome ⁇ c and has a glass transition temperature in the range 25- 35 °C
  • This optical preform is then placed in a bifocal mold (FT-28) of matching base curve and desired add curve, and rotated to achieve the angular orientation between the axis of the add power segment and the tone axis of the CR-39 single vision lens called for by the prescription
  • the mold assembly is then placed in a curing chamber equipped with ultraviolet lamps and a programable heater The mold assembly is heated a predetermined temperature at which the adjacent layer sta ⁇ s to flow and assumes the shape
  • An optical preform includes an optical a ⁇ icle consisting of a single vision lens of aspheric geometry made of polycarbonate of bisphenol A to which a first adjacent layer is added
  • the first adjacent layer is overcoated with a second adjacent layer of different composition
  • the first adjacent layer consists of a pa ⁇ ially polymerized copolymer of mono- and di-functional acrylates and methacrylates to which unreacted multifunctional acrylates and excess unreacted photoimtiators are provided
  • the second layer is also a pa ⁇ ially polymerized, non-cross-linked copolymer of acrylates and methacrylates, but incorporates a highly functionalized acrylate or styrenic cross-linker to impa ⁇ scratch resistance, as well as unreacted excess photoinitiator.
  • This optical preform is packaged.
  • a release paper is provided to protect the integrity of the adjacent layers and to protect the surface from dust.
  • the optical preform is placed in a glass mold that matches the base curvature of the preform and has a desired add curvature incorporating a progressive additional multifocal lens design.
  • the preform may be used as a circular lens blank, or may be edged for a frame prior to the final molding operation.
  • the toric axis of the preform is aligned to the invisible marks of the mold in order to set the toric axis according to the prescription being fitted.
  • the mold assembly is then placed in a curing chamber, and the cure of the adjacent layers completed as in the first embodiment.
  • the curing process develops an outer hard scratch resistant layer on the convex surface of the finished progressive addition lens, utilizing the second adjacent coating.
  • the inner adjacent coating flows to fill the cavity between the single vision lens and the glass mold, and hence is instrumental in developing the progressive addition geometry.
  • Example 3 This example illustrates the application of the adjacent layer on the concave surface of a single vision lens to form the optical preform.
  • the single vision lens is cast from a formulation of bisphenol A diacrylate, styrene and divinyl benzene. It has a refractive index of 1.60.
  • a liquid resin formulation is made up of a mixture of an end-capped bisphenol A, monoacrylate, monoallyl terminated bisphenol A diesters, a monofunctional aliphatic acrylate ester, and a photo-polymerization initiator, such as Irgacure 184.
  • a specified volume of this liquid resin formulation is added to the concave surface of the single vision lens, pliable spacers are placed on the edge of the single vision lens, and a glass mold transparent to ultraviolet radiation in the wavelength range 320-390nm is placed over the liquid resin formulation in order to spread it out and form a layer of predetermined thickness.
  • the mold assembly is subjected to a cure cycle consisting of exposure to ultraviolet radiation and a heat ramp. After cure, the optical preform is removed from the mold, cleaned and packaged prior to shipment.
  • This example involves the application of a pa ⁇ ially cured polymerizable resin layer on the concave surface of a disposable mold.
  • a plastic disposable mold made of a styrenic copolyme r is coated with a viscous, liquid, polymerizable resin layer and then exposed to ultraviolet radiation from a lamp.
  • the layer is cured to form a polymerized layer with a cross-link density less than lxlO 4 moles/liter.
  • the layer is then impregnated with additional multifunctional monomers and photoinitiators.
  • the layer is 50-150 microns in thickness.
  • the disposable mold may be spherical or aspheric in geometry and may be of single focus or multifocal optical geometry.
  • the volume of resin added to the mold in order to form the conformal layer depends on the magnitude of the add power of the bifocal style of the add.
  • the pre-coated mold is coated with a release paper, then shipped to a retail or manufacturing site.
  • an optical preform whose power corresponds to the distance power of the finished lens is selected, then placed on the pre-coated mold with its toric axis oriented at an angle relative to the axis of the add power of the mold called for in the prescription.
  • the mold assembly is placed in a curing chamber and subject to an initial thermal cycle in order to soften or liquify the conformal layer and allow it to form a close contact with the surface of the optical preform and form close contact with it.
  • a finished bifocal or multifocal lens is obtained after the curing process is completed.

Landscapes

  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Ophthalmology & Optometry (AREA)
  • Mechanical Engineering (AREA)
  • Casting Or Compression Moulding Of Plastics Or The Like (AREA)
  • Eyeglasses (AREA)
  • Optical Couplings Of Light Guides (AREA)

Abstract

Cette préforme optique (10), constituée d'un article optique tel qu'une lentille de vision simple, est pourvue d'une couche adjacente d'une résine partiellement durcie (20), laquelle peut se conformer à un moule (30) et être ensuite durcie afin de modifier les propriétés optiques de la préforme (10). En outre, on peut d'abord placer cette couche de résine partiellement durcie (20) sur l'article optique (10) avant de placer ce dernier contre le moule (30). Dans un autre mode de réalisation, on peut d'abord placer la couche de résine partiellement durcie (20) sur la surface du moule (30) avant de placer l'article optique (10) contre celui-ci (30).
EP97908998A 1996-03-11 1997-03-11 Preforme pour lentilles optiques Withdrawn EP0944471A4 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US61533696A 1996-03-11 1996-03-11
US615336P 1996-03-11
PCT/US1997/003766 WO1997033742A1 (fr) 1996-03-11 1997-03-11 Preforme pour lentilles optiques

Publications (2)

Publication Number Publication Date
EP0944471A1 EP0944471A1 (fr) 1999-09-29
EP0944471A4 true EP0944471A4 (fr) 2001-04-04

Family

ID=24464926

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97908998A Withdrawn EP0944471A4 (fr) 1996-03-11 1997-03-11 Preforme pour lentilles optiques

Country Status (9)

Country Link
EP (1) EP0944471A4 (fr)
JP (1) JP2000506794A (fr)
CN (2) CN1214007A (fr)
AU (1) AU734592B2 (fr)
BR (1) BR9709442A (fr)
CA (1) CA2248832A1 (fr)
EA (1) EA199800815A1 (fr)
IL (1) IL126125A0 (fr)
WO (1) WO1997033742A1 (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2793038B1 (fr) 1999-04-29 2002-01-25 Essilor Int Lentille ophtalmique composite et procede d'obtention d'une telle lentille
US7368072B2 (en) * 2001-12-10 2008-05-06 Ppg Industries Ohio, Inc. Photochromic contact lenses and methods of manufacturing
ES2368349T5 (es) * 2007-07-05 2021-09-17 Satisloh Ag Procedimiento de bloqueo de un primordio de lente, composición adhesiva y uso de este último para el bloqueo de las lentes
US8318055B2 (en) 2007-08-21 2012-11-27 Johnson & Johnson Vision Care, Inc. Methods for formation of an ophthalmic lens precursor and lens
US8317505B2 (en) * 2007-08-21 2012-11-27 Johnson & Johnson Vision Care, Inc. Apparatus for formation of an ophthalmic lens precursor and lens
US8313828B2 (en) * 2008-08-20 2012-11-20 Johnson & Johnson Vision Care, Inc. Ophthalmic lens precursor and lens
US8252369B2 (en) 2008-05-21 2012-08-28 Essilor International (Compagnie Generale D'optique) Process for applying a coating onto a fresnel lens forming surface
US9417464B2 (en) 2008-08-20 2016-08-16 Johnson & Johnson Vision Care, Inc. Method and apparatus of forming a translating multifocal contact lens having a lower-lid contact surface
US9084977B2 (en) 2010-12-29 2015-07-21 Ivanhoe Htl Petroleum Ltd. Method, system, and apparatus for lift gas distribution
MY179469A (en) * 2013-09-30 2020-11-06 Alcon Inc Method for making uv-absorbing ophthalmic lenses
US9645412B2 (en) 2014-11-05 2017-05-09 Johnson & Johnson Vision Care Inc. Customized lens device and method
CN104440415B (zh) * 2014-12-29 2017-04-12 成都精密光学工程研究中心 一种抛光工艺
JP5873584B1 (ja) * 2015-03-12 2016-03-01 株式会社ホプニック研究所 プラスチックレンズの製造方法、フィルムの位置決め方法
CN105058656A (zh) * 2015-09-09 2015-11-18 李峰 玻璃覆膜制作方法
US10359643B2 (en) 2015-12-18 2019-07-23 Johnson & Johnson Vision Care, Inc. Methods for incorporating lens features and lenses having such features
EP3561576A1 (fr) * 2018-04-24 2019-10-30 Carl Zeiss Vision International GmbH Verre de lunettes comprenant au moins un verre mince et son procédé de fabrication

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4544572A (en) * 1982-09-07 1985-10-01 Minnesota Mining And Manufacturing Company Coated ophthalmic lenses and method for coating the same
US4774035A (en) * 1986-01-14 1988-09-27 Camelot Industries Corporation Process of coating an ophthalmic lens

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0764033B2 (ja) * 1983-09-07 1995-07-12 ミノルタ株式会社 接合形光学部材及びその製造方法
US5219497A (en) * 1987-10-30 1993-06-15 Innotech, Inc. Method for manufacturing lenses using thin coatings

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4544572A (en) * 1982-09-07 1985-10-01 Minnesota Mining And Manufacturing Company Coated ophthalmic lenses and method for coating the same
US4544572B1 (fr) * 1982-09-07 1994-01-04 Signet Armorlite, Inc.
US4774035A (en) * 1986-01-14 1988-09-27 Camelot Industries Corporation Process of coating an ophthalmic lens

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO9733742A1 *

Also Published As

Publication number Publication date
EA199800815A1 (ru) 1999-04-29
CN1322620A (zh) 2001-11-21
IL126125A0 (en) 1999-05-09
AU2075597A (en) 1997-10-01
BR9709442A (pt) 1999-08-10
EP0944471A1 (fr) 1999-09-29
CA2248832A1 (fr) 1997-09-18
JP2000506794A (ja) 2000-06-06
AU734592B2 (en) 2001-06-21
CN1214007A (zh) 1999-04-14
WO1997033742A1 (fr) 1997-09-18

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