EP0165270A1 - Element optique avec revetement phototropique - Google Patents
Element optique avec revetement phototropiqueInfo
- Publication number
- EP0165270A1 EP0165270A1 EP85900064A EP85900064A EP0165270A1 EP 0165270 A1 EP0165270 A1 EP 0165270A1 EP 85900064 A EP85900064 A EP 85900064A EP 85900064 A EP85900064 A EP 85900064A EP 0165270 A1 EP0165270 A1 EP 0165270A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- phototropic
- optical element
- element according
- lacquer
- coating
- 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.)
- Pending
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 34
- 238000000576 coating method Methods 0.000 title claims abstract description 24
- 239000011248 coating agent Substances 0.000 title claims abstract description 21
- 239000000126 substance Substances 0.000 claims abstract description 25
- 239000004922 lacquer Substances 0.000 claims abstract description 22
- 238000004040 coloring Methods 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 11
- 230000001681 protective effect Effects 0.000 claims description 5
- 239000003381 stabilizer Substances 0.000 claims description 4
- -1 polysiloxane Polymers 0.000 claims description 3
- 229920001296 polysiloxane Polymers 0.000 claims description 3
- 239000006096 absorbing agent Substances 0.000 claims description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
- 230000006378 damage Effects 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 3
- 239000003973 paint Substances 0.000 claims 3
- 239000004593 Epoxy Substances 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- SYFOAKAXGNMQAX-UHFFFAOYSA-N bis(prop-2-enyl) carbonate;2-(2-hydroxyethoxy)ethanol Chemical compound OCCOCCO.C=CCOC(=O)OCC=C SYFOAKAXGNMQAX-UHFFFAOYSA-N 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 239000005340 laminated glass Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229920000515 polycarbonate Polymers 0.000 claims 1
- 239000004417 polycarbonate Substances 0.000 claims 1
- 229920000193 polymethacrylate Polymers 0.000 claims 1
- 229920002635 polyurethane Polymers 0.000 claims 1
- 239000004814 polyurethane Substances 0.000 claims 1
- 239000005368 silicate glass Substances 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 238000004043 dyeing Methods 0.000 description 7
- 230000005540 biological transmission Effects 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 238000005282 brightening Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000037072 sun protection Effects 0.000 description 3
- 239000003086 colorant Substances 0.000 description 2
- 239000005357 flat glass Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/685—Compositions containing spiro-condensed pyran compounds or derivatives thereof, as photosensitive substances
-
- 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 invention relates to an optical element with a phototropic coating, for example a sun protection spectacle lens.
- Optical elements with phototropic coatings i.e. Coatings, the coloring of which changes in intensity and color impression in accordance with the ambient lighting, are known, for example, from DE-OS 29 26 255.
- This document describes two ways in which a phototropic coating can be applied to an optical element.
- a mixture of the phototropic substance and an optically clear plastic material is produced and this mixture is applied to the optical element.
- the phototropic substance is first dissolved in a solvent; the optical element is then immersed in the solution for several hours.
- Coating is that the coatings are either lengthy to produce, adhere poorly and / or the optical quality of the optical element is reduced.
- the object of the invention is to develop an optical element with a phototropic coating in such a way that the easily applied coating adheres well and does not impair the optical quality of the element.
- This object is achieved in that the coating consists of a lacquer in which one or more phototropic substances are introduced.
- the lacquer can be applied to the front and back of the optical element or only on one side.
- a protective lacquer is used as the lacquer, as is usually used to protect plastic glasses against mechanical and / or other effects.
- This has the additional advantage that no additional operation is required to apply the phototropic coating in plastic glasses; rather, the optical element, for example a spectacle lens, is given the phototropic coating by the application of the protective lacquer, which is in any case necessary to protect against external influences.
- the lacquer can have several layers, the phototropic coloring of which can be different. Mixed colors and / or colored patterns can be generated in this way.
- one or more phototropic substances can also be introduced into the optical element.
- phototropic compounds such as saturation transmission, kinetics of darkening and brightening, temperature dependence and lifespan of the phototropic effect, transmission in the brightened state and also the color impression depend to a large extent on the chemical environment of the phototropic compounds, i.e. the matrix into which phototropic substances are introduced.
- the many phototropic substances if they are introduced into a lacquer according to the invention, have a longer service life with regard to the phototropic effect than when they are introduced, for example, into the plastic material of the optical element.
- the optical element and / or the coating can further be colored according to claim 4 additionally in a manner known per se non-phototropically.
- the optical element is a spectacle lens
- the lens may not be optically clear, but rather be provided with a certain "initial absorption".
- both the phototropic and the non-phototropic coloring can be homogeneous or partial.
- the coloring can be gradual, for example in such a way that the coloring decreases from the top edge of the glass downwards.
- the phototropic or photochromic substances can be introduced either gradually in the coating or in the optical element itself.
- the matrix of the phototropic compound and thus the properties of the phototropic compound for example with regard to the kinetics of the coloring, life To influence saturation transmission, color etc.
- stabilizers to the phototropic lacquer which prevent photooxidative and / or photolytic aging or destruction of the phototropic compounds introduced into the lacquer and / or the optical element, for example by atmospheric oxygen and / or UV rays or at least delay it.
- the stabilizers can UV absorbers of the usual type, such as benzophenone, benzotriazole Be acrylic acid derivatives.
- the stabilizers described in DE-OS 33 10 388 can be used, for example.
- phototropic or photochromic compounds or substances can be used as phototropic or photochromic compounds or substances, as described, for example, in US Pat. Nos. 3,562,172 and 3,578,602 or in DE-OS 29 36 255.
- the phototropic compounds according to claim 12 are particularly advantageous with regard to temperature stability and service life.
- Elements needs the phototropic substance in the case of the usual diffusion coloring of the CR 39 material over eight times as long to lighten up to half the darkening than when the inventive introduction.
- Polysiloxane base with a layer thickness of approx. 3 ⁇ m was colored phototropically.
- the specified transmission values are V-weighted.
- Brightening is significantly faster, a brightening to 70% of the maximum transmission is achieved in 2.5 minutes instead of only in 20 minutes.
- Substances lie in the fact that already known phototropic compounds can be used as sun protection filters at all or even at low temperatures.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Paints Or Removers (AREA)
- Eyeglasses (AREA)
- Surface Treatment Of Optical Elements (AREA)
- Optical Fibers, Optical Fiber Cores, And Optical Fiber Bundles (AREA)
- Optical Filters (AREA)
- Optical Measuring Cells (AREA)
Abstract
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19833345639 DE3345639A1 (de) | 1983-12-16 | 1983-12-16 | Optisches element mit phototropem ueberzug |
DE3345639 | 1983-12-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0165270A1 true EP0165270A1 (fr) | 1985-12-27 |
Family
ID=6217197
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP84115603A Expired - Lifetime EP0146136B1 (fr) | 1983-12-16 | 1984-12-17 | Elément optique revêtu d'une couche phototropique |
EP85900064A Pending EP0165270A1 (fr) | 1983-12-16 | 1984-12-17 | Element optique avec revetement phototropique |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP84115603A Expired - Lifetime EP0146136B1 (fr) | 1983-12-16 | 1984-12-17 | Elément optique revêtu d'une couche phototropique |
Country Status (6)
Country | Link |
---|---|
EP (2) | EP0146136B1 (fr) |
JP (1) | JPH0736064B2 (fr) |
AT (1) | ATE52859T1 (fr) |
AU (1) | AU585492B2 (fr) |
DE (2) | DE3345639A1 (fr) |
WO (1) | WO1985002687A1 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9341184B2 (en) | 2009-12-22 | 2016-05-17 | Smith & Nephew, Inc. | Disposable pumping system and coupler |
Families Citing this family (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1246565A (fr) * | 1984-07-06 | 1988-12-13 | Shinichi Yamamoto | Composes a base de spiro-oxazine; leur preparation; articles mis en forme, photochromiques |
AU564689B2 (en) * | 1985-07-09 | 1987-08-20 | Kureha Kagaku Kogyo K.K. | Photochromic lens |
GB8610709D0 (en) * | 1986-05-01 | 1986-06-04 | Plinkington Bros Plc | Photochromic lenses |
US5017225A (en) * | 1987-12-02 | 1991-05-21 | Japan Capsular Products Inc. | Microencapsulated photochromic material, process for its preparation and a water-base ink composition prepared therefrom |
DE4024330A1 (de) * | 1990-07-31 | 1992-02-06 | Huels Troisdorf | Verfahren zur herstellung einer photochromen folie |
DE4220251C2 (de) * | 1991-06-20 | 1996-10-17 | Rodenstock Optik G | Photochromes optisches Kunststoffelement |
DE4316362A1 (de) * | 1993-05-15 | 1994-11-17 | Curt Petermann | Verfahren und Vorrichtung zur Einstellung des Lichtdurchlasses durch Glasscheiben und Vorrichtung zur Durchführung des Verfahrens |
DE4422663A1 (de) * | 1993-06-28 | 1995-01-19 | Rodenstock Optik G | Photochrom eingefärbter transparenter Gegenstand |
AUPN007194A0 (en) * | 1994-12-16 | 1995-01-19 | Sola International Holdings Ltd | Method of preparing photochromic article |
AU704802B2 (en) * | 1994-12-16 | 1999-05-06 | Carl Zeiss Vision Australia Holdings Ltd | Method of preparing photochromic article |
DE19547327C2 (de) * | 1995-12-19 | 1999-08-26 | Daimler Chrysler Ag | Schichtaufbau mit einem photochromen Material, Verfahren zu dessen Herstellung sowie dessen Verwendung |
EP0963390B1 (fr) | 1997-02-21 | 2003-05-02 | PPG Industries Ohio, Inc. | Couche photochromique de polyurethanne et articles ayant une telle couche |
AU2001231128A1 (en) | 2000-02-04 | 2001-08-14 | Ppg Industries Ohio, Inc. | Photochromic coated articles |
US6531076B2 (en) | 2000-02-04 | 2003-03-11 | Ppg Industries Ohio, Inc. | Photochromic organic resin composition |
US8017720B2 (en) | 2005-12-16 | 2011-09-13 | Ppg Industries Ohio, Inc. | Sulfur-containing oligomers and high index polyurethanes prepared therefrom |
US7465414B2 (en) | 2002-11-14 | 2008-12-16 | Transitions Optical, Inc. | Photochromic article |
US11149107B2 (en) | 2004-09-01 | 2021-10-19 | Ppg Industries Ohio, Inc. | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
US11008418B2 (en) | 2004-09-01 | 2021-05-18 | Ppg Industries Ohio, Inc. | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
US11248083B2 (en) | 2004-09-01 | 2022-02-15 | Ppg Industries Ohio, Inc. | Aircraft windows |
US9464169B2 (en) | 2004-09-01 | 2016-10-11 | Ppg Industries Ohio, Inc. | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
US20090280709A1 (en) | 2004-09-01 | 2009-11-12 | Ppg Industries Ohio, Inc. | Polyurethanes, Articles and Coatings Prepared Therefrom and Methods of Making the Same |
US20090280329A1 (en) | 2004-09-01 | 2009-11-12 | Ppg Industries Ohio, Inc. | Polyurethanes, Articles and Coatings Prepared Therefrom and Methods of Making the Same |
US11591436B2 (en) | 2004-09-01 | 2023-02-28 | Ppg Industries Ohio, Inc. | Polyurethane article and methods of making the same |
US9598527B2 (en) | 2004-09-01 | 2017-03-21 | Ppg Industries Ohio, Inc. | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
DE102006012552A1 (de) * | 2006-03-18 | 2007-09-20 | Terporten Gmbh | Farbiges Glaselement |
US8206463B2 (en) | 2006-05-04 | 2012-06-26 | Bayer Materialscience Llc | Colored article of manufacture and a process for its preparation |
CN101437874B (zh) | 2006-05-05 | 2011-09-21 | Ppg工业俄亥俄公司 | 硫醚官能的低聚多硫醇以及由其制备的制品 |
DE102011106827B4 (de) | 2011-07-07 | 2014-01-23 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verfahren zum Überziehen eines lichtdurchlässigen Trägers mit einer phototropen Schicht sowie eine demgemäß beschichtete Kunststofffolie |
WO2023208941A1 (fr) | 2022-04-26 | 2023-11-02 | Essilor International | Article optique photochromique ayant un revêtement miroir |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1391063A (fr) * | 1964-01-20 | 1965-03-05 | Saint Gobain | Dispositif antiéblouissant |
FR1394163A (fr) * | 1964-02-18 | 1965-04-02 | Saint Gobain | Compositions photochromes notamment pour la fabrication de vitrages à transmission variable |
FR1406487A (fr) * | 1964-02-18 | 1965-07-23 | Saint Gobain | Nouvelles compositions photochromes notamment pour la fabrication des vitrages à transmission variable |
US3409554A (en) * | 1964-03-16 | 1968-11-05 | Nasa Usa | Gd or sm doped silicon semiconductor composition |
GB1105825A (en) * | 1964-10-30 | 1968-03-13 | American Cyanamid Co | Photochromic materials |
US3397023A (en) * | 1964-12-16 | 1968-08-13 | Polaroid Corp | Light apertures |
GB1146309A (en) * | 1965-06-25 | 1969-03-26 | Nuclear Res Associates Inc | Improvements in or relating to phototropic composition |
US3409556A (en) * | 1966-01-04 | 1968-11-05 | American Cyanamid Co | Photochromic composition and substrate coated therewith |
GB1186987A (en) * | 1967-08-30 | 1970-04-08 | Fuji Photo Film Co Ltd | Photochromic Compounds |
DE1927849A1 (de) * | 1969-05-31 | 1970-12-10 | Licentia Gmbh | Spiroverbindung |
US3707397A (en) * | 1971-02-26 | 1972-12-26 | Owens Illinois Inc | Process for providing uniform organopolysiloxane coatings on polycarbonate and acrylic surfaces |
US4043637A (en) * | 1973-06-15 | 1977-08-23 | American Optical Corporation | Photochromic light valve |
JPS5315743B2 (fr) * | 1973-08-14 | 1978-05-26 | ||
DD127943B1 (de) * | 1976-10-22 | 1980-01-30 | Reinhard Bartel | Fotochromes material mit verbesserten sensitometrischen eigenschaften |
CA1105784A (fr) * | 1977-01-24 | 1981-07-28 | Bernard L. Laurin | Traduction non-disponible |
SU755388A1 (ru) * | 1977-09-27 | 1980-08-15 | Gi Proekt Montazhu Oboru Na Pr | Способ изготовления сферических оболочек1 |
US4215010A (en) * | 1978-09-08 | 1980-07-29 | American Optical Corporation | Photochromic compounds |
EP0082115A3 (fr) * | 1981-12-10 | 1984-02-22 | Ciba-Geigy Ag | Article photochromique |
-
1983
- 1983-12-16 DE DE19833345639 patent/DE3345639A1/de active Granted
-
1984
- 1984-12-17 EP EP84115603A patent/EP0146136B1/fr not_active Expired - Lifetime
- 1984-12-17 EP EP85900064A patent/EP0165270A1/fr active Pending
- 1984-12-17 DE DE8484115603T patent/DE3482286D1/de not_active Expired - Lifetime
- 1984-12-17 AU AU37861/85A patent/AU585492B2/en not_active Ceased
- 1984-12-17 AT AT84115603T patent/ATE52859T1/de not_active IP Right Cessation
- 1984-12-17 WO PCT/DE1984/000276 patent/WO1985002687A1/fr not_active Application Discontinuation
- 1984-12-17 JP JP60500239A patent/JPH0736064B2/ja not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
---|
See references of WO8502687A1 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9341184B2 (en) | 2009-12-22 | 2016-05-17 | Smith & Nephew, Inc. | Disposable pumping system and coupler |
Also Published As
Publication number | Publication date |
---|---|
WO1985002687A1 (fr) | 1985-06-20 |
JPS61501171A (ja) | 1986-06-12 |
AU585492B2 (en) | 1989-06-22 |
DE3482286D1 (de) | 1990-06-21 |
EP0146136A2 (fr) | 1985-06-26 |
AU3786185A (en) | 1985-06-26 |
EP0146136B1 (fr) | 1990-05-16 |
DE3345639C2 (fr) | 1988-09-15 |
EP0146136A3 (en) | 1985-07-24 |
ATE52859T1 (de) | 1990-06-15 |
JPH0736064B2 (ja) | 1995-04-19 |
DE3345639A1 (de) | 1985-07-04 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Designated state(s): AT BE CH DE FR GB LI LU NL SE |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE |
|
17P | Request for examination filed |
Effective date: 19851220 |
|
XX | Miscellaneous (additional remarks) |
Free format text: VERFAHREN ABGESCHLOSSEN INFOLGE VERBINDUNG MIT 84115603.7/0146136 (EUROPAEISCHE ANMELDENUMMER/VEROEFFENTLICHUNGSNUMMER) VOM 05.03.87. |
|
RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: MARTINUZZI, GIUSEPPE Inventor name: EFFER, ERHARD Inventor name: MELZIG, MANFRED |