GB969754A - Transparent optical viewing device - Google Patents

Transparent optical viewing device

Info

Publication number
GB969754A
GB969754A GB2308060A GB2308060A GB969754A GB 969754 A GB969754 A GB 969754A GB 2308060 A GB2308060 A GB 2308060A GB 2308060 A GB2308060 A GB 2308060A GB 969754 A GB969754 A GB 969754A
Authority
GB
United Kingdom
Prior art keywords
spiro
benzopyran
indoline
trimethyl
nitro
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.)
Expired
Application number
GB2308060A
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.)
NCR Voyix Corp
National Cash Register Co
Original Assignee
NCR Corp
National Cash Register Co
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 NCR Corp, National Cash Register Co filed Critical NCR Corp
Publication of GB969754A publication Critical patent/GB969754A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
    • C07D311/86—Oxygen atoms, e.g. xanthones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/10—Spiro-condensed systems
    • 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
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts
    • G02C7/10—Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses
    • G02C7/102—Photochromic filters
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts
    • G02C7/10—Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses
    • G02C7/108—Colouring materials
    • 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

Abstract

The following photochromic compounds can be prepared by the methods indicated below: IV. 1,3,3-trimethyl-61-nitro-81-allyl-spiro (21H-11-benzopyran-2,21-indoline), V. 1,3,3-trimethyl-61-chloro-81-nitro-spiro (21H-11-benzopyran-2,21-indoline), VI. 1,3,3-trimethyl-61,81-dibromo-spiro(21H -11-benzopyran-2,21-indoline), VII. 1,3,3-trimethyl-61-bromo-spiro (21H-11-benzopyran-2,21-indoline), VIII. 1,3,3-trimethyl-71-chloro-spiro (21H-11-benzopyran-2,21-indoline), IX. 1,3,3-trimethyl-61-chloro-spiro (21H -11-benzopyran-2,21-indoline), X. 1,3,3-trimethyl-5,61-dinitro-spiro (21H -11-benzopyran-2,21-indoline), XI. 1,3,3-trimethyl-61,81-dinitro-spiro (21H -11-benzopyran-2,21-indoline), XII. 1,3,3-trimethyl-51-nitro-spiro (21H -11-benzopyran-2,21-indoline), XIII. 1,3,3-trimethyl-71-nitro-spiro (21H -11-benzopyran-2,21-indoline), XIV. 1,3,3-trimethyl-71-nitro-spiro (21H -11-beta-naphthopyran, 2,21-indoline), XVI. 3-methyl-6-nitro-8-methoxy-spiro[2H-1-benzopyran-2,21 -(21H-11-beta-naphtho-pyran)], XVII. 1,3,3-trimethyl-81-nitro-spiro-(21H -11-benzopyran-2,21-indoline), XVIII. 1,3,3-trimethyl-51-nitro-81-methoxy-spiro -(21H-11-benzopyran-2,21-indoline), XIX. 1,3,3-trimethyl-spiro-(21H-11-benzopyran -2,21-indoline), XX. 1,3,3-trimethyl-51-chloro-spiro-(21H-11 -benzopyran-2,21-indoline), XXI. 1,3,3-trimethyl-81-fluoro-spiro-(21H-11 -benzopyran-2,21-indoline), XXII. 1,3,3-trimethyl-5-nitro-61-bromo-spiro-(21H -11-benzopyran-2,21-indoline), XXIII. 1,3,3-trimethyl-61-hydroxy-spiro-(21H -11-benzopyran-2,21-indoline), XXIV. 1,3,3-trimethyl-61-nitro-71-chloro-spiro -(21H-11-benzopyran-2,21-indoline), XXV. 1,3,3-trimethyl-51,71-dihydroxy-spiro-(21H -11-benzopyran-2,21-indoline), XXVI. 1,3,3-trimethyl-51,71-dimethoxy-spiro-(21H -11-benzopyran-2,21-indoline), XXVII. 1,3,3-trimethyl-81-allyl-spiro-(21H-11 -benzopyran-2,21-indoline), XXVIII. 1,3,3-trimethyl-81-methoxy-spiro-(21H-11 -benzopyran-2,21-indoline), XXX. 3-phenyl-71-nitro-spiro-[2H-1-benzopyran-2,21 -(21H-11-beta-naphthopyran)], XXXI. 3-methyl-6-nitro-spiro-[2H-1-benzopyran-2,21-(21 -11-benzopyran)], XXXII. 1,3,3-trimethyl-61-methoxy-81-nitro-spiro -(21H-11-benzopyran-2,21-indoline), XXXIII. 1,3,3-trimethyl-5-methoxy-61,81-dibromo-spiro -(21H-11-benzopyran-2,21-indoline), XXXIV. 1,3,3-trimethyl-5-methoxy-61-nitro-spiro-(21H -11-benzopyran-2,21-indoline), XXXV. 1,3,3-trimethyl-7-methoxy-71-chloro-spiro-(21H -11-benzopyran-2,21-indoline), XXXVI. 1,3,3-trimethyl-7,81-dimethoxy-61-nitro-spiro -(21H-11-benzopyran-2,21-indoline), XXXVII. 1,3,3-trimethyl-5-chloro-51,61-dinitro,81\h -methoxy-spiro-(21H-11-benzopyran-2, 21-indoline), XXXVIII. 1,3,3-trimethyl-5-chloro-51-nitro-81-methoxy -spiro-(21H-11-benzopyran-2,21-indoline), XXXIX. 1,3-dimethyl-3-isopropyl-61-nitro-spiro-(21H -11-benzopyran-2,21-indoline), XLI. 71-nitro-spiro-[xantho-10,21-(21H-11 -benzo-beta-naphthopyran)], XLIV. 1,3,3,81-tetramethyl-51-hydroxymethyl-spiro -[21H-11-pyridino-([3,4-b])pyran]-2,21-indoline, XLV. 1,3,3-trimethyl-61-nitro-81-methoxy-spiro -(21H-11-benzopyran-2,21-indoline), and XLVI. 1,3,3-trimethyl-61-nitro-spiro-(21H-11 -benzopyran-2,21-indoline). Compounds IV-XIII, XVII-XXVIII, XXXII-XXXIX, XLV and XLVI can be prepared by condensing a substituted or unsubstituted 2-methylene-1,3,3 -trimethyl indoline with a correspondingly substituted salicylaldehyde in ethanol; compound XIV by condensing 6-nitro-2-hydroxy-1-naphthaldehyde with 2-methylene-1,3,3-trimethylindoline; compound XVI by condensing 3-methoxy-5-nitro-salicylaldehyde with methyl ethyl ketone and condensing the product with 2-hydroxy-1-naphthaldehyde; compound XXX by condensing 4-nitro-salicylaldehyde with phenyl ethyl ketone and condensing the product with 2-hydroxy-1-naphthaldehyde; compound XXXI by condensing 5-nitro-salicylaldehyde with 2-hydroxystyryl ethyl ketone and treating with sodium carbonate; compound XLI by condensing 6-nitro-2-hydroxy-1-naphthaldehyde with 9-methyl-xanthenol; and compound XLIV as for compound XIV but using pyridoxal in place of 6-nitro-2-hydroxy-1-naphthaldehyde. 9-methyl-xanthenol is obtained by reacting xanthone with methyl magnesium iodide and hydrolyzing the product. Various solvents for the compounds are referred to. Specifications 883,803, 887,902, 887,958, 889,186 and 889,586 are referred to.ALSO:A device for interposing between the eyes and incident light, e.g. a pair of spectacles, for preventing the transmission of an excess of harmful radiations to the eyes comprises in conjunction a solid transparent medium and one or a combination of photochromic spiropyran compounds in liquid, semi-solid or solid solution, which when subjected to incident light abnormally rich in U.V. radiation changes its light-absorbing properties to effect at least a reduction in the transmission of the U.V. radiation through the medium. A coloured dyestuff can be used with the photochromic compounds. The darkening of the device may be initiated by an activating light source preceding a burst of U.V. light, and, after darkening, an auxiliary light source or heating appliance may be used to cause reversion of the photochromic compounds to a transparent condition, if ambient normal light and temperature are <PICT:0969754/C4-C5/1> <PICT:0969754/C4-C5/2> <PICT:0969754/C4-C5/3> insufficient. The heating may be supplied by an external application of heat or by electric heating wires embedded in the device. In the construction shown in Fig. 2 a liquid solution 21 of photochromic material is contained in a closed transparent cell 19 of glass, quartz, cellulose nitrate, gelatin, cellulose acetate, polyvinylidene chloride or polyvinyl alcohol &c. The outer walls of the cell may be optically flat or optically corrected. In the construction shown in Fig. 3 two transparent sheets 23 and 24 hold between them a semi-solid solution of photochromic material. Fig. 4 shows a transparent support sheet 27 having thereon a coating of minute transparent capsules 28 each containing a droplet of a solution of a photochromic material. The capsules 28 can be coated with a lacquer of acrylic resin to reduce the scattering of reflected light, the resin being selected to have a transparency and refractive index close to that of the capsule walls. Other constructions are a self-supporting continuous film containing cells filled with a solution of photochromic compounds and a transparency in which a photochromic compound or compounds are included in solid solution with a self-supporting film material. Several transparencies containing different photochromic compounds can be laminated together. Many photochromic compounds, their methods of preparation, and solvents therefor are referred to. Specifications 883,803, 887,902, 887,958, 889,186 and 889,586 are referred to.
GB2308060A 1959-07-14 1960-07-01 Transparent optical viewing device Expired GB969754A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US82742059A 1959-07-14 1959-07-14

Publications (1)

Publication Number Publication Date
GB969754A true GB969754A (en) 1964-09-16

Family

ID=25249178

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2308060A Expired GB969754A (en) 1959-07-14 1960-07-01 Transparent optical viewing device

Country Status (2)

Country Link
DE (2) DE1148351B (en)
GB (1) GB969754A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2312376A1 (en) * 2004-07-02 2011-04-20 ESSILOR INTERNATIONAL (Compagnie Générale d'Optique) Photochromic optical component
CN101367989B (en) * 2008-08-07 2011-06-08 上海金发科技发展有限公司 Preparation method for transparent plastic for ultraviolet protection
US9885808B2 (en) 2012-03-08 2018-02-06 Consejo Superior De Investigaciones Cientificas(Csic) Coating with photochromic properties, method for producing said coating and use thereof applicable to optical articles and glazed surfaces

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3212898A (en) * 1962-11-21 1965-10-19 American Cyanamid Co Photosensitive compositions of matter comprising photochromic materials suspended in polyester binders

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE960767C (en) * 1951-08-05 1957-03-28 Dr Georg Walter Kuehl Process for the production of a multilayer glass with light transmission that can be changed by changing the color
DE952030C (en) * 1951-09-18 1956-11-08 Dr Georg Walter Kuehl Multi-layer glass, especially for anti-glare and heat protection ticks with a plastic intermediate layer colored by metal salts and a process for its production
BE566862A (en) * 1957-04-23

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2312376A1 (en) * 2004-07-02 2011-04-20 ESSILOR INTERNATIONAL (Compagnie Générale d'Optique) Photochromic optical component
CN101367989B (en) * 2008-08-07 2011-06-08 上海金发科技发展有限公司 Preparation method for transparent plastic for ultraviolet protection
US9885808B2 (en) 2012-03-08 2018-02-06 Consejo Superior De Investigaciones Cientificas(Csic) Coating with photochromic properties, method for producing said coating and use thereof applicable to optical articles and glazed surfaces

Also Published As

Publication number Publication date
DE1894003U (en) 1964-06-04
DE1148351B (en) 1963-05-09

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