EP0246114A2
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Photochromic spiropyran compounds
Assignee: BAE Systems Electronics Ltd
•
Filing: 1987-05-15
•
Granted: —
•
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 colour 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 George Heller
- 👤 Stephen Nigel Oliver
- 👤 John Whittall
- 👤 Ian Tomlinson
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-09 05:15
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: 23
Claim 1
Independent Claim
20 words
Photochromic spiro-benzopyrans and spiro-naphthopyrans 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-naphthopyrans in which a spiro-adamantane group is present in the 2-position of the benzopyran or naphthopyran ring.
Claim 3
Dependent Claim
77 words
Photochromic spiropyrans having the general formula I, II, or III set forth below in which R₃ to R₁₀ independently represent hydrogen, lower alkyl, (l to 5 carbon atoms), aryl, alkoxy, hydroxy, alkyl- or dialkylamino, halogen or a heterocyclic group, with the proviso that R³ or R⁴ is not hydroxy, alkoxy, or alkyl- or dialkylamino or in the case of formula I, II, or III the benzene or naphthalene ring is benzannelated or annelated with a heterocyclic ring.
Claim 4
Dependent Claim
77 words
Photochromic spiropyrans having the general formula I, II, or III set forth below in which R₃ to R₁₀ independently represent hydrogen, lower alkyl, (l to 5 carbon atoms), aryl, alkoxy, hydroxy, alkyl- or dialkylamino, halogen or a heterocyclic group, with the proviso that R³ or R⁴ is not hydroxy, alkoxy, or alkyl- or dialkylamino or in the case of formula I, II, or III the benzene or naphthalene ring is benzannelated or annelated with a heterocyclic ring.
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
20 words
A photochromic spiropyran according to claim 2 having the general formula (II) and which is benzannelated in the R⁵-R⁶ positions.
Claim 7
Dependent Claim
30 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 R⁶-R⁷ or R⁵-R⁶ or R⁷-R⁸ positions.
Claim 8
Dependent Claim
17 words
A photochromic spiropyran according to any one of claims 2 to 5, wherein R³-R⁴ are both hydrogen.
Claim 9
Dependent Claim
19 words
A photochromic spiropyran according to claim 6, wherein R³ is hydrogen and R⁴ is methyl, phenyl, paramethoxy-phenyl or halogen.
Claim 10
Dependent Claim
63 words
A heliochromic spiro-naphthopyran having the following general formula:- wherein R⁵ to R¹⁰ 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 R⁶-R⁷, R⁵-R⁶ or R⁷-R⁸ positions and R⁴ represents hydrogen, alkyl, halogen or an aryl group.
Claim 11
Dependent Claim
63 words
A heliochromic spiro-naphthopyran having the following general formula:- wherein R⁵ to R¹⁰ 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 R⁶-R⁷, R⁵-R⁶ or R⁷-R⁸ positions and R⁴ represents hydrogen, alkyl, halogen or an aryl group.
Claim 12
Dependent Claim
17 words
A heliochromic spiro-naphthopyran according to claim 8, wherein R⁶ is phenyl, chlorine, para-methoxyphenyl methoxy, thienyl or furyl.
Claim 13
Dependent Claim
44 words
l0. A heliochromic spiropyran having the following general formula:- wherein R¹ and R² 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
44 words
l0. A heliochromic spiropyran having the following general formula:- wherein R¹ and R² 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
36 words
A heliochromic spiropyran having the following general formula:- wherein R⁵ to R⁸ represent hydrogen, lower alkyl, halogen, alkoxy, alkoxyaryl or a 5 or 6-membered heterocyclic group or R⁶ and R⁷ together represent a fused pyrone ring.
Claim 16
Dependent Claim
36 words
A heliochromic spiropyran having the following general formula:- wherein R⁵ to R⁸ represent hydrogen, lower alkyl, halogen, alkoxy, alkoxyaryl or a 5 or 6-membered heterocyclic group or R⁶ and R⁷ together represent a fused pyrone ring.
Claim 17
Dependent Claim
49 words
An ophthalmic or plano lens which darkens in sunlight and reverts to a pale or colourless condition in white light at normal ambient temperature wherein the lens has incorporated therein or coated thereon an effective amount of a heliochromic compound as claimed in any one of the preceding claims.
Claim 18
Dependent Claim
22 words
A lens according to claim l2, in which the lens is formed from a polycarbonate, alkyl acrylate or alkyl methacrylate plastics material.
Claim 19
Dependent Claim
21 words
A lens according to claim l2, in which the lens is formed from a polymer of a dialkylene glycol bis(allyl carbonate).
Claim 20
Dependent Claim
33 words
A lens according to claim l2, l3 or l4, wherein two or more heliochromic compounds are employed in conjunction in order to achieve a brown or grey shade in the sunlight- darkened state.
Claim 21
Dependent Claim
39 words
A one-step Claisen rearrangement process for the preparation of chromene derivatives which comprises heating a phenol with a propargyl alcohol derivative in a solvent at a temperature of less than about l80°C and in the presence of a catalyst.
Claim 22
Dependent Claim
39 words
A one-step Claisen rearrangement process for the preparation of chromene derivatives which comprises heating a phenol with a propargyl alcohol derivative in a solvent at a temperature of less than about l80°C and in the presence of a catalyst.
Claim 23
Dependent Claim
20 words
A process according to claim l6 wherein the propargyl alcohol derivative is a propargyl acetate and the catalyst is alumina.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
Maintenance schedule is calculated for granted US utility patents.