Optical element with a phototropic coating.
Abstract
The coating consists of a lacquer comprising one or a plurality of phototropic substances. The lacquer may have a plurality of layers of which the phototropic coloration may differ. The optical element may further comprise one or a plurality of phototropic substances. Furthermore, the optical element and the coating may have a non phototropic coloration in a manner known per se.

Term
Term ended
Projected expiry passed 17 December 2004, 21.8 years ago.
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12 claims: 12 independent, 0 dependent
- 1Optical element with a phototropic coating, characterized in that the coating consists of a lacquer into which one or more phototropic substances have been introduced. 1. Optisches Element mit einem phototropen Überzug, dadurch gekennzeichnet, daß der Überzug aus einem Lack besteht, in den eine oder mehrere phototrope Substanzen eingebracht sind.
- 2Element nach Anspruch 1, dadurch gekennzeichnet, daß der Lack mehrere Schichten aufweist, deren phototrope Einfärbung unterschiedlich sein kann. 2nd Element according to claim 1, characterized in that the lacquer has several layers, the phototropic coloring of which can be different.
- 3Element nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß zusätzlich in das optische Elenent eine oder mehrer phototrope Substanzen eingebracht sind. 3rd Element according to claim 1 or 2, characterized in that one or more phototropic substances are additionally introduced into the optical element.
- 4Element nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß das optische Element und der Überzug zusätzlich in an sich bekannter Weise nicht-phototrop eingefärbt sind. 4th Element according to one of claims 1 to 3, characterized in that the optical element and the coating are additionally colored non-phototropically in a manner known per se.
- 5Element according to claim 3 or 4, characterized in that the optical element is a laminated glass composed of several layers which can be colored differently phototropically or non-phototropically. 5. Element nach Anspruch 3 oder 4, dadurch gekennzeichnet, daß das optische Element ein aus mehreren Schichten aufgebautes Verbundglas ist, die unterschiedlich phototrop oder nicht-phototrop eingefärbt sein können.
- 6Element according to one of claims 1 to 5, characterized in that the phototropic coloring of the coating and / or the optical element and / or the non-phototropic coloring of the optical element and coating is partially different and in particular is gradual. 6. Element nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, daß die phototrope Einfärbung des Überzugs und/oder des optischen Elements und/oder die nichtphototrope Einfärbung des optischen Elements und Überzugs partiell unterschiedlich und insbesonder graduell verlaufend ist.
- 7Element according to one of claims 1 to 6, characterized in that the lacquer is a protective lacquer based on polysiloxane, in particular of epoxy, acryloyl, alkoxy or alkyialkoxysilanes, a copolymer of polyfunctional acrylates and N-vinyl lactams or an epoxy lacquer or a polyurethane lacquer. 7. Element nach einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, daß der Lack ein Schutzlack auf Polysiloxanbasis, insbesondere aus Epoxy-, Acryloyl-, Alkoxy- oder Alkyialkoxysilanen, ein Copolymerisat aus polyfunktionalen Acrylaten und N-Vinyl-lactamen oder ein Epoxidlack oder ein Polyurethanlack ist.
- 8Element nach Anspruch 7, dadurch gekennzeichnet, daß die phototrope Substanz oder Substanzen in den Lack in Lösung und/oder nach dessen vollständigem oder teilweisen Aushärten eingebracht sind. 8th. Element according to claim 7, characterized in that the phototropic substance or substances are introduced into the lacquer in solution and / or after its complete or partial hardening.
- 9Element according to one of claims 1 to 8, characterized in that stabilizers, such as UV absorbers such as singlet oxygen extinguishers etc., are introduced into the lacquer and in particular the protective lacquer, which prevent or at least inhibit photolytic and / or photooxidative destruction of the phototropic substance. 9. Element nach einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, daß in den Lack und insbesondere den Schutzlack Stabilisatoren, wie UV-Absorber wie Singulett-Sauerstoff-Löscher etc. eingebracht sind, die eine photolytische und/oder eine photooxidative Zerstörung der phototropen Substanz verhindern oder zumindest hemmen.
- 10Element nach einem der Ansprüche 1 bis 9, dadurch gekennzeichnet, daß das optische Element aus Diäthylenglykol-bis-allylcarbonat, Polycarbonat oder Polymethacrylat besteht. 10th Element according to one of claims 1 to 9, characterized in that the optical element consists of diethylene glycol bis-allyl carbonate, polycarbonate or polymethacrylate.
- 12Element nach einem der Ansprüche 1 bis 11, dadurch gekennzeichnet, daß die phototrope Substanz eine Verbindung der allgemeinen Formel ist, wobei die Reste R bedeuten:R1, R2, R3 einen oder mehrer Substituenten aus der Reihe -H, -CN, -SCN, -N02, -X, -CH2X, -CX3 (X=Halogen), -OR, -SR, -COR, -COOR (R=H, Alkyl mit bis zu 8 C-Atomen, Aryl, Heteroaryl), >Ar (annelierte aromatische oder heroaromatische Ringsysteme)R4, R5, R6, R7, ein Substituent aus der Reihe -H, -R, -CH2R, -NH2, -NHR, -NR2, -OR, -SR (R=Alkylrest mit bis zu 8 C-Atomen, Aryl oder Heteroarylrest) wobei mindestens einer der Reste R5 oder R6 nicht Methyl ist, falls R7=H ist. 12th Element according to one of claims 1 to 11, characterized in that the phototropic substance is a compound of the general formula, where the radicals R are:R1, R2, R3 one or more substituents from the series -H, -CN, -SCN, -N02, -X, -CH2X, -CX3 (X = halogen), -OR, -SR, -COR, -COOR (R =H, Alkyl with up to 8 carbon atoms, aryl, heteroaryl),> Ar (fused aromatic or hero-aromatic ring systems)R4, R5, R6, R7, a substituent from the series -H, -R, -CH2R, -NH2, -NHR, -NR2, -OR, -SR (R = alkyl radical with up to 8 carbon atoms, aryl or heteroaryl radical) where at least one of the radicals R5 or R6 is not methyl if R7= H is.
Independent claims12
35 paragraphs, as filed
Technical field
The invention relates to an optical element with a phototropic coating, for example a sun protection spectacle lens.
State of the art
Optical elements with phototropic coatings, ie coatings whose coloring 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. According to one method, a mixture of the phototropic substance and an optically clear plastic material, as is also used for plastic lenses, is produced and this mixture is applied to the optical element. In the other method described, the phototropic substance is first dissolved in a solvent; the optical element is then immersed in the solution for several hours.
A disadvantage of the coatings applied according to DE-OS 29 36 255 is that the coatings are either lengthy to produce, adhere poorly and / or the optical quality of the optical element is reduced.
Presentation of the invention
The invention has for its object to further develop an optical element with a phototropic coating such that the easily applied coating adheres well and does not deteriorate 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.
In particular, it is advantageous if 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, receives the phototropic coating by applying the protective lacquer which is in any case necessary to protect against external influences.
Developments of the invention are specified in the subclaims.
According to claim 2, 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. In addition, one or more phototropic substances can also be introduced into the optical element.
According to the invention, it has been recognized that in order to achieve, for example, a cosmetically appealing neutral gray or brown coloration of phototropic glasses, at least two different substances are required, the physical properties of which must be coordinated with one another in such a way that no color differences become visible during the lightening or darkening phase. This adaptation of the overall system to the desired properties can - as has also been recognized according to the invention - be carried out by suitable selection and / or variation of the respective matrix in which the various phototropic substances are embedded.
The properties of 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 the phototropic substances are introduced.
In this way, it is possible according to the invention to achieve different colors and / or different kinetics of lightening and darkening by varying the phototropic substances and / or the lacquer in which the phototropic compounds are incorporated.
Surprisingly, 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. For example, if the optical element is a spectacle lens, the lens may not be optically clear, but rather be provided with a certain "initial absorption".
Of course, both the phototropic and the nonphototropic coloring can be homogeneous or partial. In the case of sun protection glasses in particular, the coloring can be gradual, for example in such a way that the coloring decreases from the top edge of the glass towards the bottom. In the case of photroper gradual coloring, the phototropic or photochromic substances can be introduced either gradually in the coating or in the optical element itself.
Various advantageous protective lacquers are specified in claim 7. The choice of different types of lacquer and the different application methods specified in claim 8 make it possible - as already mentioned - to achieve a different response and even a different color impression with the same phototropic connection.
In addition, it is possible, for example by curing the lacquer with ionizing radiation, in the presence of initiator systems or by photoinitiators and by exposure to heat or UV radiation, 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.
In particular, it is possible, according to claim 9, to add 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 be UV absorbers of the usual type, such as benzophenone, benzotriazole acrylic acid derivatives. Furthermore, the stabilizers described in DE-OS 33 10 388 can be used, for example.
Various possible materials for the optical element are characterized in claims 10 and 11.
Of course, a wide variety of compounds 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. However, the phototropic compounds according to claim 12 are particularly advantageous with regard to temperature stability and service life.
Way of carrying out the invention
The invention is explained in more detail below on the basis of comparisons with optical elements, the phototropic effect of which has been generated in a conventional manner.
Comparison 1
Flat glass panes made of CR 39 with a thickness of 2 mm are once in with the phototropic substance 1,3,3, -trimethyl-8'-methoxy-6'nitro-2'H-1'bezopyran known from US Pat. No. 2,953,454 conventional dip dyeing (analogous to DE-OS 2 347 018) and once with a coating according to the invention based on polysiloxane with a layer thickness of approx.
The table below shows the change in the optical density OD (V-weighted) and the half-life HWZ of the brightening at various temperatures after a 15-minute exposure with a 150 W XBO lamp with an illuminance of 50 klux:<tables id="tabl0001" num="0001"><img file="EP0146136A2_D0001.tif" /></tables>
In spite of minor changes in the optical density of the optical element produced with conventional dip coloring, the phototropic substance in the case of the usual diffusion coloring of the CR 39 material takes over eight times as long to brighten to half the darkening than in the case of the introduction according to the invention.
Comparison 2
Flat glass panes made of CR 39 with a thickness of 2 mm are made with the phototropic substance 1,3,3, -trimethyl-spiro (indoline-2,3'naphth (2,1-6) (1 - 6)) known from US Pat. No. 3,578,602 , 4) -oxazine) once in conventional dip dyeing (analogous to US Pat. No. 3,578,602) and once with a coating according to the invention based on polysiloxane with a layer thickness of approx.
The table below shows the darkening and brightening at 5 ° C. An illuminance of 50 klux was maintained during a 15-minute exposure. The specified transmission values are V-weighted.<tables id="tabl0002" num="0002"><img file="EP0146136A2_D0002.tif" /></tables><tables id="tabl0003" num="0003"><img file="EP0146136A2_D0003.tif" /></tables>
In the case of the dyeing according to the invention, in which the phototropic substance is introduced into a lacquer, over 94% of the maximum darkening is achieved in one minute, with more conventional. In contrast, dyeing technology only 56%. The brightening is also significantly faster, a brightening to 70% of the maximum transmission is achieved in 2.5 minutes instead of only in 20 minutes.
The advantage of introducing phototropic substances according to the invention is that already known phototropic compounds can be used as sun protection filters at all or even at low temperatures.
4 sheets
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| Document | Relation | Office | Cited during |
|---|---|---|---|
| GB2179174B | Cited by | United Kingdom | Search report |
| GB2179174A | Cited by | United Kingdom | Search report |
| DE102006012552A1 | Cited by | Germany | Search report |
| EP0245020A3 | Cited by | European Patent Office (EPO) | Search report |
| US4756973A | Cited by | United States of America | Search report |
| EP0346484A4 | Cited by | European Patent Office (EPO) | Search report |
| US9822211B2 | Cited by | United States of America | Applicant |
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| EP0171909A1 | Cited by | European Patent Office (EPO) | Search report |
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| EP0346484A1 | Cited by | European Patent Office (EPO) | Search report |
| FR2584833A1 | Cited by | France | Search report |
| US6187444B1 | Cited by | United States of America | Applicant |
| EP0082115A2 | Cites | European Patent Office (EPO) | Search report |
| GB1092123A | Cites | United Kingdom | Search report |
| GB1092124A | Cites | United Kingdom | Search report |
| GB1105825A | Cites | United Kingdom | Search report |
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| FR1391063A | Cites | France | Search report |
| DE1927849A1 | Cites | Germany | Search report |
| GB2029410A | Cites | United Kingdom | Search report |
| DE2746131A1 | Cites | Germany | Search report |
| DE2826255A1 | Cites | Germany | Examiner |
| US3397023A | Cites | United States of America | Search report |
| US3409556A | Cites | United States of America | Search report |
14 members in 6 offices
Priority claims5
| Document | Office | Kind | Date |
|---|---|---|---|
| 3345639 | Germany | A | |
| 3345639 | Germany | A | |
| 3345639 | Germany | – | |
| 3345639 | – | – | – |
| DE19833345639 | – | – | – |
Members14
| Document | Office | Kind | |
|---|---|---|---|
| WO8502687A1 | World Intellectual Property Organization (WIPO) | A1 | |
| AU3786185A | Australia | A | |
| EP0146136A2This record | European Patent Office (EPO) | A2 | |
| DE3345639A1 | Germany | A1 | |
| EP0146136A3 | European Patent Office (EPO) | A3 | |
| EP0165270A1 | European Patent Office (EPO) | A1 | |
| JPS61501171A | Japan | A | |
| DE3345639C2 | Germany | C2 | |
| AU585492B2 | Australia | B2 | |
| EP0146136B1 | European Patent Office (EPO) | B1 | |
| AT52859T | Austria | T | |
| ATE52859T1 | Austria | T1 | |
| DE3482286D1 | Germany | D1 | |
| JPH0736064B2 | Japan | B2 |
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| Miscellaneous (additional remarks)VERBUNDEN MIT 85900064.8/0165270 (EUROPAEISCHE ANMELDENUMMER/VEROEFFENTLICHUNGSNUMMER) DURCH ENTSCHEIDUNG VOM 05.03.87.XX | XX | EP | |
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| Miscellaneous (additional remarks)VERBUNDEN MIT 85900064.8/0165270 (EUROPAEISCHE ANMELDENUMMER/VEROEFFENTLICHUNGSNUMMER) DURCH ENTSCHEIDUNG VOM 05.03.87.XX | XX | EP | |
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Numbers
- Publication
- 0146136
- Publication, DOCDB
- 0146136
- Publication, EPODOC
- EP0146136
- Application
- 84115603
- Application, DOCDB
- 84115603
- Application, EPODOC
- EP19840115603
Titles3
- German
- Optisches Element mit phototropem Überzug
- English
- Optical element with a phototropic coating
- French
- Elément optique revêtu d'une couche phototropique
Classification
- CPC, 2
- G03C1/685
- G02B5/23
- IPC, 9
- G02C7 10
- C03C27 12
- C07D498 10
- G02B1 10
- G02B5 23
- G02F1 17
- G03C1 685
- G03C1 72
- G03C1 73
Designated states11
- Contracting states, 11
- Austria
- Belgium
- Switzerland
- Germany
- France
- United Kingdom
- Italy
- Liechtenstein
- Luxembourg
- Netherlands (Kingdom of the)
- Sweden