US4685783A
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Polychromic tetracyclo-spiro-adamatylidene derivatives, and polychromic lens incorporating said compounds
Assignee: GEC-MARONI Ltd
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Filing: 1984-09-05
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Granted: 1987-08-11
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Expires: 2004-09-05
Abstract
Abstract A series of photochromic compounds are disclosed which have the property of undergoing a reversible color change when exposed to unfiltered sunlight and reverting to their original color in the absence of U.V. light at room temperature. These compounds have the general formula: ##STR1## represents an adamantylidene or a substituted adamantylidene group; R 1 represents hydrogen, alkyl, aryl, aralkyl or a heterocyclic group, X represents oxygen or > NR 2 , in which R 2 is hydrogen, aryl, alkyl or aralkyl and ##STR2## represents an aromatic group, an unsaturated heterocyclic group or a benzannelated heterocyclic group. The photochromic compounds of the invention are useful in the manufacture of photoreactive lenses, particularly plastic lenses.
Inventors
- 👤 Harold H. Heller
- 👤 Stephen N. Oliver
- 👤 John Whittal
- 👤 William Johncock
- 👤 Paul J. Darcy
- 👤 Clive Trundle
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 17:14
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/54; C07D307/77; C07D307/78; C07D307/79; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/22; C07D333/24; C07D333/26; C07D333/38; C07D333/50; C07D333/52; C07D333/54; C07D333/56; C07D333/60; C07D409/00; C07D409/02; C07D409/06; C07D493/00; C07D493/02; C07D493/10; C07D495/00; C07D495/02; C07D495/10; G; G03; G03C; G03C1/00; G03C1/72; G03C1/73
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
86 words
A compound having the following general formula: ##STR10## ##STR11## represents an adamantylidene; R 1 represents hydrogen, lower alkyl, phenyl or phenyl alkyl; X represents oxygen or >NR 2 , in which R 2 is hydrogen, lower alkyl, phenyl or phenyl alkyl and ##STR12## is a 2,5-, 2,4- or 3,5-dimethoxybenzo, a 2- or 3-furano, or a 2- or 3-thiopheno group, which Y groups are unsubstituted or may be substituted by one to four members selected from the group consisting of deuterium, lower alkyl, nitro, halogen, or phenyl.
Claim 2
Dependent Claim
86 words
A compound having the following general formula: ##STR10## ##STR11## represents an adamantylidene; R 1 represents hydrogen, lower alkyl, phenyl or phenyl alkyl; X represents oxygen or >NR 2 , in which R 2 is hydrogen, lower alkyl, phenyl or phenyl alkyl and ##STR12## is a 2,5-, 2,4- or 3,5-dimethoxybenzo, a 2- or 3-furano, or a 2- or 3-thiopheno group, which Y groups are unsubstituted or may be substituted by one to four members selected from the group consisting of deuterium, lower alkyl, nitro, halogen, or phenyl.
Claim 3
Dependent Claim
32 words
A compound according to claim 1 in which the furano or thiopheno is substituted with one or two members selected from the group consisting of deuterium, lower alkyl, nitro, halogen or phenyl.
Claim 4
Dependent Claim
17 words
A compound according to claim 1 in which R 1 is a lower alkyl or phenyl group.
Claim 5
Dependent Claim
19 words
A compound according to claim 1 in which the ring represented by ##STR13## is a thiophenol or furano group.
Claim 6
Dependent Claim
169 words
A photoreactive ophthalmic or plano lens having a heliochromic compound coated on a surface thereof or laminated or incorporated in the material of the lens, the heliochromic compound having the property of reversibly forming a coloured structural form on irradiation with U.V. light and returning to a colourless or paler structural form at normal ambient temperature in the absence of U.V. stimulation, the coloured form having the following structure (a) ##STR14## and being capable of conversion to its colourless or paler form (b) by formation of a central 6-membered ring, wherein ##STR15## represents an adamentylidene; R 1 represents hydrogen, lower alkyl, phenyl, or phenyl alkyl; X represents oxygen or >NR 2 , in which R 2 is hydrogen, lower alkyl, phenyl or phenyl alkyl and ##STR16## is a 2,5-, 2,4- or 3,5-dimethoxybenzo, a 2- or 3-furano, or a 2- or 3-thiopheno group, which Y groups are unsubstituted or may be substituted by one to four members selected from the group consisting of deuterium, lower alkyl, nitro, halogen, or phenyl.
Claim 7
Dependent Claim
169 words
A photoreactive ophthalmic or plano lens having a heliochromic compound coated on a surface thereof or laminated or incorporated in the material of the lens, the heliochromic compound having the property of reversibly forming a coloured structural form on irradiation with U.V. light and returning to a colourless or paler structural form at normal ambient temperature in the absence of U.V. stimulation, the coloured form having the following structure (a) ##STR14## and being capable of conversion to its colourless or paler form (b) by formation of a central 6-membered ring, wherein ##STR15## represents an adamentylidene; R 1 represents hydrogen, lower alkyl, phenyl, or phenyl alkyl; X represents oxygen or >NR 2 , in which R 2 is hydrogen, lower alkyl, phenyl or phenyl alkyl and ##STR16## is a 2,5-, 2,4- or 3,5-dimethoxybenzo, a 2- or 3-furano, or a 2- or 3-thiopheno group, which Y groups are unsubstituted or may be substituted by one to four members selected from the group consisting of deuterium, lower alkyl, nitro, halogen, or phenyl.
Claim 8
Dependent Claim
21 words
A photoreactive lens according to claim 5 wherein the lens is formed from a polycarbonate or a polyalkyl methacrylate or acrylate.
Claim 9
Dependent Claim
36 words
A photoreactive ophthalmic or plano lens which comprises a blend of heliochromic compounds, as claimed in claim 1 or claim 2, coated on a surface thereof or laminated or incorporated in the material of the lens.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-08-10 | 1991-02-09 | 1991-08-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-08-10 | 1995-02-09 | 1995-08-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-08-10 | 1999-02-09 | 1999-08-11 | $7700.00 | Window Closed / Lapsed |