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WO1994027169A1 - Lentille - Google Patents

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Publication number
WO1994027169A1
WO1994027169A1 PCT/AT1994/000065 AT9400065W WO9427169A1 WO 1994027169 A1 WO1994027169 A1 WO 1994027169A1 AT 9400065 W AT9400065 W AT 9400065W WO 9427169 A1 WO9427169 A1 WO 9427169A1
Authority
WO
WIPO (PCT)
Prior art keywords
lens
liquid
crystal
liquid single
elastomer
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.)
Ceased
Application number
PCT/AT1994/000065
Other languages
German (de)
English (en)
Inventor
Werner Fiala
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.)
BIFOCON OPTICS FORSCHUNGS- und ENTWICKLUNGS GmbH
Original Assignee
BIFOCON OPTICS FORSCHUNGS- und ENTWICKLUNGS GmbH
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 BIFOCON OPTICS FORSCHUNGS- und ENTWICKLUNGS GmbH filed Critical BIFOCON OPTICS FORSCHUNGS- und ENTWICKLUNGS GmbH
Publication of WO1994027169A1 publication Critical patent/WO1994027169A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61FFILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/02Prostheses implantable into the body
    • A61F2/14Eye parts, e.g. lenses or corneal implants; Artificial eyes
    • A61F2/145Corneal inlays, onlays, or lenses for refractive correction
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61FFILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/02Prostheses implantable into the body
    • A61F2/14Eye parts, e.g. lenses or corneal implants; Artificial eyes
    • A61F2/16Intraocular lenses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61FFILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/02Prostheses implantable into the body
    • A61F2/14Eye parts, e.g. lenses or corneal implants; Artificial eyes
    • A61F2/16Intraocular lenses
    • A61F2/1613Intraocular lenses having special lens configurations, e.g. multipart lenses; having particular optical properties, e.g. pseudo-accommodative lenses, lenses having aberration corrections, diffractive lenses, lenses for variably absorbing electromagnetic radiation, lenses having variable focus
    • A61F2/1616Pseudo-accommodative, e.g. multifocal or enabling monovision
    • A61F2/1618Multifocal lenses
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041Lenses
    • G02B1/043Contact lenses

Definitions

  • the invention relates to an ophthalmic lens made of at least one birefringent material, as well as processes for its production and the use of special birefringent materials for ophthalmic lenses.
  • Multifocal birefringent lenses in general and multifocal birefringent ophthalmic lenses in particular are already known per se.
  • the corresponding concepts are e.g. published in US Pat. Nos. 4,981,342, 5,073,021 and 5,142,411, in European Application EP-0 308 705 A2, and in PCT / AT91 / 00042 (Publication No. WO 91/14189) .
  • United States Patent 4,981,342 stated that polymers according to United States Patent 4,384,107; 4,393,194; 4,933,196; 4,433,132; 4,446,305; 4,461,888; 4,461,887; 4,503,248; 4,520,189; 4,521,588; 4,575,413; 4,575,547; 4,608,429 and 4,626,125 can be made birefringent by stretching, and thus in lenses or lens systems according to USA 4,981,342 could be used.
  • birefringent plastics basically represent thermoplastics of high polarizability, which are deformed (stretched) linearly by applying an external mechanical field and which become optically birefringent due to the anisotropy that occurs during this stretching process.
  • a disadvantage of stretched birefringent thermoplastics is that the often high degrees of stretching required to achieve the desired birefringence necessitate a high mechanical anisotropy of these birefringent materials, which, for example, makes machining very difficult or impossible.
  • the object of the invention is to create a precisely producible lens for ophthalmic purposes from birefringent material, and to specify methods for the production thereof.
  • liquid single crystal elastomer or a liquid single crystal duromer is used as the birefringent material.
  • Liquid single-crystal elastomers or duromers are special liquid-crystalline elastomers or duromers with a fixed anisotropic network structure.
  • Liquid-crystalline elastomers and -duromers are polymer networks which, for. B. can be produced in that the polymer chains of liquid crystalline side chain polymers are linked together by bifunctional molecules. In these materials, the chain segments and the mesogenic groups are movable above the glass transition temperature, but the material as such retains its dimensional stability as a result of the crosslinking. In the mechanically unloaded state, the orientation of the nematic director of the mesogenic groups is macroscopically inconsistent and the elastomer appears opaque. However, if a sample of an elastomeric material such. B. an elastomer film above stretched uniaxially, the directors of the mesogenic groups orient themselves parallel to the direction of the tensile stress. The sample becomes transparent and corresponds in its optical properties to a single crystal of the same dimension. If the elastomer sample is relieved, it returns to the disordered, opaque state due to its elasticity.
  • elastomers containing reactive residues with at least one unreacted functional group are uni- or biaxially oriented in a first step by the action of a mechanical tension, and this orientation in one subsequent second step fixed by linking at least some of the reactive radicals with polymer chains.
  • liquid single crystals In contrast to conventional liquid crystal polymers, liquid single crystals, and in particular liquid single crystal elastomers and liquid single crystal duromers with a fixed anisotropic network structure, have only been known for a few years. Such systems were first described in 1991 in Macromol.Chem.Rapid Commun. 12, 717-726 (1991), the new expression "liquid single crystal elastomer” (original: “liquid single crystal elastomer, LSCE”) also being coined. These novel liquid single-crystal polymers and duromers and their preparation are described in detail in German patent application DE 41 24 859 A1 and in international application PCT / EP92 / 01591 (WO 93/03114).
  • these liquid single crystals can be given both the properties of elastomers and of duromers; the total crosslinking density for elastomers is typically between 2 and 20%, for duromers i.a. over 50%.
  • liquid single-crystal elastomers or duromers can be produced in practically any geometry and size.
  • newer machining processes such as eroding or cutting with Lasers can be used to produce curved surfaces.
  • a variety of such methods are mentioned, for example, in patent class B23K 26/00.
  • neodymium and C0 2 ⁇ lasers are used for processing plastics.
  • the evaporation or decomposition products obtained are predominantly gaseous; any decomposition products adhering to the processed body can be removed by a subsequent polishing step.
  • liquid single-crystal elastomers in contact lenses is advantageous because elastomers have a high gas permeability, which ensures the necessary supply of oxygen to the cornea. Furthermore, elastomers have the material characteristics of soft contact lenses, with the wearing comfort of soft contact lenses being considered to be particularly high.
  • Liquid single-crystal thermosets have a comparatively lower gas permeability, but give a contact lens greater dimensional stability and also better optical properties.
  • liquid single-crystal elastomers in bi- and multifocal intraocular lenses is appropriate when the lens is to be folded or rolled up during the implantation process.
  • Monofocal intraocular lenses are made, for example, of optical quality silicone rubber; the lens is implanted in folded form and unfolds again in the eye due to the elasticity of the lens material.
  • the advantage of such lenses is that the surgical incision of the cornea required for implantation can be very small ("single stitch implantation").
  • the optical egg Properties of such lenses generally lag behind those of fixed lenses.
  • the gas permeability of elastomers is irrelevant for intraocular lenses.
  • thermosets in bi- and multifocal intraocular lenses are appropriate if special importance is attached to the good optical quality of the lens.
  • the invention further relates to a method for producing a lens from a birefringent liquid single crystal elastomer or liquid single crystal duro, and the use of these materials in ophthalmic lenses.
  • FIGS. 1 a and 1 b show a highly schematic first exemplary embodiment for producing a lens according to the invention.
  • 2a, 2b and 2c show a second manufacturing process in a schematic representation.
  • 3a to 3e show a third manufacturing method.
  • 4a and 4b show an alternative shape for shaping a lens.
  • 5a, 5b and 5c schematically show a further embodiment of a manufacturing method according to the invention.
  • a lens that is to say a transparent optical component with at least one curved surface, from a liquid single-crystal elastomer or duromer
  • the methods described below can advantageously be used.
  • a lens will have two opposite, differently curved lens surfaces, especially if it is intended for ophthalmic purposes.
  • Typical are biconvex, biconcave, plano-convex, plano-concave, concave-convex and convex-concave lens shapes.
  • Other lens shapes are also conceivable for special cases.
  • liquid-crystalline elastomer made stable in shape by pre-cross-linking is initially assumed.
  • liquid-crystalline elastomers from which the liquid single-crystal elastomers / duromers with fixed anisotropic network structure are then formed, can preferably be selected from the group of elastomers of the formula I,
  • Sp is a bivalent spacer group
  • V is a polymer chain crosslinking group
  • R is a reactive radical containing at least one unreacted functional group.
  • Formula I describes the preferred elastomers only in a highly schematic manner. So it is z. B. does not require that each main chain unit carries an esogenic unit. Formula I is also intended to include copolymers with different polymer chain units. In addition, the number of groups V, R and Sp - B generally does not match. Despite these shortcomings, Formula I appears to be suitable for the diagrammatic representation of the preferred elastomers and is therefore used.
  • liquid-crystalline elastomers in particular of the formula I, is carried out analogously to known polymerization processes, as described in the literature (for example in the standard works such as Ocian, Principles of Polymerization, McGraw Hill, New
  • a liquid-crystalline elastomer for example of the above formula I, is stretched inaxially by the action of a mechanical stress. By applying a mechanical tension, an orientation in the Elastomer is generated and this orientation is "chemically frozen" in a second crosslinking process. A liquid single-crystal elastomer is thus obtained.
  • An example of a cuboid body 1 made of a liquid single-crystal elastomer is shown in FIG.
  • material for example milling or grinding
  • one or more bifocal lenses 2 can now be formed from this body 1, as shown in FIG. 1b.
  • the optical axis is provided with the reference number 3. It runs straight in the finished lens 2.
  • the elastomer can preferably be cooled below the glass transition temperature.
  • this glass transition temperature can be selected below body temperature and preferably below room temperature, so that the lens exhibits an elastomeric behavior in these temperature ranges.
  • the sample can of course also be processed at a temperature above the glass transition temperature.
  • the optical axis 3 is "bent", that is to say in all cuts with cutting planes which are parallel to the plane formed by the axis of rotational symmetry and the optical axes, the optical axis is curved in a circle.
  • the imaging quality of such a lens for the extraordinary rays is only insignificantly affected as long as the angles between the incident light rays and the optical axes are close to 90 °.
  • the orientation of the optical axes is irrelevant for the ordinary rays anyway.
  • the first is used for the synthesis of a liquid-crystalline elastomer network, in which there is no orientation yet, but there is already a certain dimensional stability.
  • the second crosslinking process is used to freeze an orientation generated by mechanical stress.
  • the third crosslinking process then serves to maintain the outer shape of the raw lens. The degree of crosslinking or the crosslinking density is increased with each crosslinking process.
  • Fig. 3a come back.
  • a second crosslinking takes place before the mold is opened and the tension is released.
  • This second networking has a dual function. On the one hand, it freezes the orientation or double refraction caused by the tension, on the other hand, this crosslinking also maintains the external shape predetermined by the mold halves 4a and 4b, so that a molded liquid single-crystal elastomer 1 "is obtained
  • Liquid single-crystal elastomers can, as is schematically indicated in FIG. 3e by vertical lines, separate the areas outside the mold in order to obtain a birefringent body with a curved surface, that is to say a pre-lens.
  • one of the two lens surfaces can then be machined, as in FIG. 2c, for example.
  • the method shown in FIGS. 3a to 3e still permits a particularly advantageous variant, which is particularly promising if the two lens radii are not significantly different from one another.
  • a one-part mold 4c can also be used, which has openings 9 in the region of curvature, via these openings 9 a negative pressure under the film 6 or the liquid single crystal which arises after crosslinking -Elastomer 1 "are generated, so that an adaptation to the concave shape 4c is possible despite the application of a tension via the tensioning device 6.
  • a lens 2 is also produced, in which the lens surfaces no longer have to be machined.
  • the starting point is a circular plate of an already anisotropically oriented liquid single crystal elastomer.
  • This plate 1 of FIG. 5a is now placed in a lens mold 4a, 4b, in which the two radii of the mold have the complementary values of the radii of the lens to be produced.
  • the mold is closed, which results in the plate 1 being deformed (FIG. 5b).
  • these reshapings must remain small in order not to cause the plate 1 to reorient. This is the case if the two radii of the lens have only slightly different or concentric values.
  • liquid single crystal elastomer was particularly treated.
  • other polymers are also conceivable and possible, in particular duromers.
  • the deformability of the resulting lens can be adjusted via the crosslinking density or degree of crosslinking.
  • Liquid single-crystal partial lenses can also be combined with a partial lens made of another material to form a structural unit.
  • the invention is not limited to the lens shape shown in the exemplary embodiments. Rather, other lens shapes are also conceivable and possible, in particular those which are known for ophthalmic purposes.

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  • Health & Medical Sciences (AREA)
  • Ophthalmology & Optometry (AREA)
  • Cardiology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Transplantation (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Vascular Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)

Abstract

L'invention concerne une lentille ophtalmique composée d'au moins un matériau biréfringent, ledit matériau utilisé étant un élatomère à monocristal liquide (1) ou un duromère à monocristal liquide. L'invention concerne en outre un procédé permettant de produire ce type de lentilles.
PCT/AT1994/000065 1993-05-14 1994-05-13 Lentille Ceased WO1994027169A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AT0095693A ATA95693A (de) 1993-05-14 1993-05-14 Linse
ATA956/93 1993-05-14

Publications (1)

Publication Number Publication Date
WO1994027169A1 true WO1994027169A1 (fr) 1994-11-24

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Family Applications (1)

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PCT/AT1994/000065 Ceased WO1994027169A1 (fr) 1993-05-14 1994-05-13 Lentille

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AT (1) ATA95693A (fr)
WO (1) WO1994027169A1 (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2305256A (en) * 1995-07-19 1997-04-02 Peter John Mckay Photochromic or polarising contact lens
WO1997038344A1 (fr) * 1996-04-05 1997-10-16 Polaroid Corporation Ebauches de verres a polariseur aligne
GB2365993A (en) * 2000-08-18 2002-02-27 Colin William Martin Light reducing contact lens
EP2276394A4 (fr) * 2008-04-28 2011-08-17 Crt Technology Inc Système et procédé de traitement et de prévention d'une perte de l'acuité visuelle
US8246167B2 (en) 2009-12-17 2012-08-21 Crt Technology, Inc. Systems and methods for the regulation of emerging myopia
EP2106566A4 (fr) * 2007-01-22 2012-09-12 E Vision Llc Lentille electro-active flexible
DE112006003257B4 (de) * 2005-12-28 2016-02-11 Gkn Driveline International Gmbh Verfahren zur Herstellung von Bälgen mit vorvernetztem thermoplastisch elastomerem Material
WO2018219671A1 (fr) * 2017-06-01 2018-12-06 Carl Zeiss Meditec Ag Cristallin artificiel à structure biréfringente produite par laser et procédé de fabrication d'un cristallin artificiel
US10359645B2 (en) 2014-02-04 2019-07-23 Paragon Crt Company Llc Multifunction contact lens
US11298222B2 (en) 2017-06-01 2022-04-12 Carl Zeiss Meditec Ag Artificial eye lens with diffractive grating structure and method for producing an artificial eye lens
US11344405B2 (en) 2017-06-01 2022-05-31 Carl Zeiss Meditec Ag Artificial eye lens having medicine repository formed therein, and method for producing an artificial eye lens

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4384107A (en) * 1981-03-02 1983-05-17 Polaroid Corporation Polyamide comprising substituted biphenylene or substituted stilbene radicals
US4981342A (en) * 1987-09-24 1991-01-01 Allergan Inc. Multifocal birefringent lens system
DE4124859A1 (de) * 1991-07-26 1993-01-28 Merck Patent Gmbh Fluessigkristalline elastomere oder duomere mit fixierter anisotroper netzwerkstruktur

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4384107A (en) * 1981-03-02 1983-05-17 Polaroid Corporation Polyamide comprising substituted biphenylene or substituted stilbene radicals
US4981342A (en) * 1987-09-24 1991-01-01 Allergan Inc. Multifocal birefringent lens system
DE4124859A1 (de) * 1991-07-26 1993-01-28 Merck Patent Gmbh Fluessigkristalline elastomere oder duomere mit fixierter anisotroper netzwerkstruktur

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
BRANDT,KAWASAKI: "on the microscopic consequences of frozen order in liquid single crystal elastomers", MACROMOL.RAPID COMMUNICATION, vol. 15, no. 3, 1994, GERMANY, pages 251 - 257 *
F.W.DEEG ET ALIA: "ultrasonic properties of a nematic sidechain polysiloxane in the 100 mhz-1ghz range", BER.BUNSENGES.PHYS.CHEM., vol. 97, no. 10, 1993, WEINHEIM,GERMANY, pages 1312 - 1315 *
KÜPFER,FINKELMANN: "nematic liquid single crystal elastomers", MAKROMOL.CHEM.RAPID.COMMUN., vol. 12, no. 12, 1991, GERMANY, pages 717 - 726 *

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2305256A (en) * 1995-07-19 1997-04-02 Peter John Mckay Photochromic or polarising contact lens
WO1997038344A1 (fr) * 1996-04-05 1997-10-16 Polaroid Corporation Ebauches de verres a polariseur aligne
GB2365993A (en) * 2000-08-18 2002-02-27 Colin William Martin Light reducing contact lens
US10126569B2 (en) 2004-11-02 2018-11-13 E-Vision Smart Optics Inc. Flexible electro-active lens
DE112006003257B4 (de) * 2005-12-28 2016-02-11 Gkn Driveline International Gmbh Verfahren zur Herstellung von Bälgen mit vorvernetztem thermoplastisch elastomerem Material
US11474380B2 (en) 2007-01-22 2022-10-18 E-Vision Smart Optics, Inc. Flexible electro-active lens
EP2106566A4 (fr) * 2007-01-22 2012-09-12 E Vision Llc Lentille electro-active flexible
US9155614B2 (en) 2007-01-22 2015-10-13 E-Vision Smart Optics, Inc. Flexible dynamic electro-active lens
US12326617B2 (en) 2007-01-22 2025-06-10 E-Vision Smart Optics, Inc. Flexible electro-active lens
US12235524B2 (en) 2007-01-22 2025-02-25 E-Vision Smart Optics, Inc. Flexible electro-active lens
EP2276394A4 (fr) * 2008-04-28 2011-08-17 Crt Technology Inc Système et procédé de traitement et de prévention d'une perte de l'acuité visuelle
US8246167B2 (en) 2009-12-17 2012-08-21 Crt Technology, Inc. Systems and methods for the regulation of emerging myopia
US10359645B2 (en) 2014-02-04 2019-07-23 Paragon Crt Company Llc Multifunction contact lens
US11298222B2 (en) 2017-06-01 2022-04-12 Carl Zeiss Meditec Ag Artificial eye lens with diffractive grating structure and method for producing an artificial eye lens
US11344405B2 (en) 2017-06-01 2022-05-31 Carl Zeiss Meditec Ag Artificial eye lens having medicine repository formed therein, and method for producing an artificial eye lens
CN110831747A (zh) * 2017-06-01 2020-02-21 卡尔蔡司医疗技术股份公司 具有激光产生的双折射结构的人造眼睛晶状体以及生产人造眼睛晶状体的方法
US11583391B2 (en) 2017-06-01 2023-02-21 Carl Zeiss Meditec Ag Artificial eye lens with laser-generated birefringent structure and method for producing an artificial eye lens
CN110831747B (zh) * 2017-06-01 2023-12-22 卡尔蔡司医疗技术股份公司 具有激光产生的双折射结构的人造眼睛晶状体以及生产人造眼睛晶状体的方法
WO2018219671A1 (fr) * 2017-06-01 2018-12-06 Carl Zeiss Meditec Ag Cristallin artificiel à structure biréfringente produite par laser et procédé de fabrication d'un cristallin artificiel

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Publication number Publication date
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