Patent US4826977A successfully refreshed from Google Patents.
US4826977A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Photochromic spiropyran compounds
Assignee: Plessey Overseas Ltd
•
Filing: 1987-05-15
•
Granted: 1989-05-02
•
Expires: 2007-05-15
Abstract
Abstract A series of novel photochromic spiropyrans are disclosed in which a spiro-adamantane group is introduced into the 2-position of the benzopyran or naphthopyran ring. The spiropyran compounds of the invention exhibit heliochromic properties, i.e. they color in sunlight and fade rapidly at ambient temperatures in the absence of U.V. light, making them good candidates for use in the manufacture of sunglasses. The invention includes lenses which darken in sunlight and incorporate the novel spiropyrans and a process for the preparation of the spiropyran compounds.
Inventors
- 👤 Harry G. Heller
- 👤 Stephen N. Oliver
- 👤 John Whittall
- 👤 Ian Tomlinson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 05:23
CPC Classifications
C; C07; C07D; C07D311/00; C07D311/02; C07D311/04; C07D311/96; C08; C08K; C08K5/00; C08K5/04; C08K5/15; C08K5/151; C08K5/1545
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
20 words
Photochromic spiro-benzopyrans and spiro-napthopyrans in which a spiro-adamantane group is present in the 2-position of the benzopyran or naphthopyran ring.
Claim 2
Dependent Claim
20 words
Photochromic spiro-benzopyrans and spiro-napthopyrans in which a spiro-adamantane group is present in the 2-position of the benzopyran or naphthopyran ring.
Claim 3
Dependent Claim
82 words
Photochromatic spiropyrans having the general formula I, II, or III set forth below in which R 3 to R 10 independently represent hydrogen, lower alkyl, (1 to 5 carbon atoms), aryl, alkoxy, hydroxy, alkyl- or dialkylamino, halogen or a heterocyclic group, with the proviso that R 3 or R 4 is not hydroxy, alkoxy, or alkyl- or dkalkylamino or in the case of formula I, II, or III the benzene or napthalene ring is benzannelated or annelated with a heterocyclic ring. ##STR25##
Claim 4
Dependent Claim
82 words
Photochromatic spiropyrans having the general formula I, II, or III set forth below in which R 3 to R 10 independently represent hydrogen, lower alkyl, (1 to 5 carbon atoms), aryl, alkoxy, hydroxy, alkyl- or dialkylamino, halogen or a heterocyclic group, with the proviso that R 3 or R 4 is not hydroxy, alkoxy, or alkyl- or dkalkylamino or in the case of formula I, II, or III the benzene or napthalene ring is benzannelated or annelated with a heterocyclic ring. ##STR25##
Claim 5
Dependent Claim
22 words
A photochromic spiropyran according to claim 2 wherein the heterocyclic annelated ring is a five or six-membered oxygen or sulphur containing ring.
Claim 6
Dependent Claim
23 words
A photochromic spiropyran according to claim 2 having the general formula (II) and which is benzannelated in the R 5 -R 6 positions.
Claim 7
Dependent Claim
39 words
A photochromic spiropyran according to claim 3, having the general formula (I) wherein a fused thiophene, furan or pyrone ring is present in the R 6 -R 7 or R 5 -R 6 or R 7 -R 8 positions.
Claim 8
Dependent Claim
20 words
A photochromic spiropyran according to any one of claims 2 to 5, wherein R 3 -R 4 are both hydrogen.
Claim 9
Dependent Claim
21 words
A photochromic spiropyran according to claim 6, wherein R 3 is hydrogen and R 4 is methyl, phenyl, paramethoxy-phenyl or halogen.
Claim 10
Dependent Claim
77 words
A heliochromic spiro-naphthopyran having the following general formula: ##STR26## wherein R 5 to R 10 represent hydrogen, lower alkyl, chlorine, bromine, aryl, hydroxy, alkoxy, alkoxyaryl, alkyl- or dialkylamino, aminoaryl or alkylamino-aryl, or a 5 or 6-membered heterocyclic group or wherein a fused thiophene, furan or pyrone ring is present in the R 6 -R 7 , R 5 -R 6 or R 7 -R 8 positions and R 4 represents hydrogen, alkyl, halogen or an aryl group.
Claim 11
Dependent Claim
77 words
A heliochromic spiro-naphthopyran having the following general formula: ##STR26## wherein R 5 to R 10 represent hydrogen, lower alkyl, chlorine, bromine, aryl, hydroxy, alkoxy, alkoxyaryl, alkyl- or dialkylamino, aminoaryl or alkylamino-aryl, or a 5 or 6-membered heterocyclic group or wherein a fused thiophene, furan or pyrone ring is present in the R 6 -R 7 , R 5 -R 6 or R 7 -R 8 positions and R 4 represents hydrogen, alkyl, halogen or an aryl group.
Claim 12
Dependent Claim
18 words
A heliochromic spiro-naphthopyran according to claim 8, wherein R 6 is phenyl, chlorine, para-methoxyphenyl methoxy, thienyl or furyl.
Claim 13
Dependent Claim
46 words
A heliochromic spiropyran having the following general formula: ##STR27## wherein R 1 and R 2 each represent one or more substituents selected from hydrogen, lower alkyl, halogen, aryl (including substituted aryl), hydroxy, alkyl- or dialkylamino, alkoxy or a heterocyclic group and <Ad represents an adamantane group.
Claim 14
Dependent Claim
46 words
A heliochromic spiropyran having the following general formula: ##STR27## wherein R 1 and R 2 each represent one or more substituents selected from hydrogen, lower alkyl, halogen, aryl (including substituted aryl), hydroxy, alkyl- or dialkylamino, alkoxy or a heterocyclic group and <Ad represents an adamantane group.
Claim 15
Dependent Claim
41 words
A heliochromic spiropyran having the following general formula: ##STR28## wherein R 5 to R 8 represent hydrogen, lower alkyl, halogen, alkoxy, alkoxyaryl or a 5 or 6-membered heterocyclic group or R 6 and R 7 together represent a fused pyrone ring.
Claim 16
Dependent Claim
41 words
A heliochromic spiropyran having the following general formula: ##STR28## wherein R 5 to R 8 represent hydrogen, lower alkyl, halogen, alkoxy, alkoxyaryl or a 5 or 6-membered heterocyclic group or R 6 and R 7 together represent a fused pyrone ring.
References Cited (Backward Citations)
US2542386A
Cited
US3231584A
Cited
US3404861A
Cited
US3567605A
Cited
US3627690A
Cited
US3944637A
Cited
GB2146327A
Cited
EP0246114A2
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-05-01 | 1992-10-31 | 1993-05-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-05-01 | 1996-10-31 | 1997-05-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-05-01 | 2000-10-31 | 2001-05-02 | $7700.00 | Window Closed / Lapsed |