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EP0250193A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Photoreactive lenses

Assignee: BAE Systems Electronics Ltd
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Filing: 1987-06-15
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Granted: —
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Expires: 2007-06-15
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Abstract

Abstract Photoreactive plastics lenses are disclosed which are coated or impregnated with an adamantane 2-spiro-benzo or naphthopyran and with a blue colouring pho tochromic benzo- or naphthopyran having a nitrogen containing substituent in the 2-position in the pyran ring. The lenses darken in sunlight and fade rapidly at ambient temperatures in the dark or in white light which does not contain a U.V. component. The combination of the yellow/orange colouring adamantane 2-spiro pyran compound with the purple/blue colouring pyran gives a desired brown/grey colouration in the sunlight-darkened lens. The invention includes novel blue-colouring pyran compounds in which the nitrogen-containing substituent in the 2-position is a phenyl group having an amino or substituted amino or nitrogen-containing heterocyclic substituent in the ortho- or para-position of the phenyl group.

Inventors

  • 👤 Harry George Heller
  • 👤 Stephen Nigel Oliver
  • 👤 John Whittall
  • 👤 Jack Brettle
  • 👤 Martin W. Baskerville
  • 👤 Clive Trundle

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-09 05:28
CPC Classifications
G; G02; G02B; G02B1/00; C; C07; C07D; C07D295/00; C07D295/02; C07D295/027; C07D295/033; C07D311/00; C07D311/02; C07D311/78; C07D311/92; C07D493/00; C07D493/02; C07D493/04; G02B3/00; G02B5/00; G02B5/20; G02B5/22; G02B5/23

Claims Analysis

Total Claims: 23
Claim 1
Independent Claim 83 words
An opthalmic or plano-lens which darkens in sunlight and reverts to a pale or colourless condition in white light at normal ambient temperatures, wherein the lens has incorporated therein or coated thereon at least two heliochromic compounds, one of said compounds comprising an adamantane spiro-benzopyran or spironaphthopyran in which an adamantane group is present in the 2-spiro-position of the benzopyran or naphthopyran ring and a second compound comprising a benzo or naphtho­pyran having a nitrogen-containing substituent in the 2-­position of the pyran ring.
Claim 2
Dependent Claim 83 words
An opthalmic or plano-lens which darkens in sunlight and reverts to a pale or colourless condition in white light at normal ambient temperatures, wherein the lens has incorporated therein or coated thereon at least two heliochromic compounds, one of said compounds comprising an adamantane spiro-benzopyran or spironaphthopyran in which an adamantane group is present in the 2-spiro-position of the benzopyran or naphthopyran ring and a second compound comprising a benzo or naphtho­pyran having a nitrogen-containing substituent in the 2-­position of the pyran ring.
Claim 3
Dependent Claim 87 words
A lens according to claim 1 in which one of said heliochromic compounds is an adamantane-spironaphthopyran and a second heliochromic compound has the general formula:- in which R represents an alkyl group or an aryl group which may contain a nitrogen containing substituent and Rʹ represents one or more substituents selected from hydrogen, alkyl, halogen, aryl, hydroxy, alkoxy, alkyl- or dialkylamino, or a heterocyclic group and wherein the ring containing the substituent group Rʹ may be benzannelated and X represents an aryl group having a nitrogen-­containing substituent.
Claim 4
Dependent Claim 33 words
A lens according to claim 2 in which the group X is a phenyl group having an amino or substituted amino substituent or a nitrogen-containing heterocyclic substituent is in the ortho and/or para-position.
Claim 5
Dependent Claim 34 words
A lens according to claim 2 or 3 in which the group R is a phenyl group having an amino or substituted amino substituent or a nitrogen-containing heterocyclic in the ortho and/or para position.
Claim 6
Dependent Claim 95 words
A lens according to claim 2 in which the second heliochromic compound has the following general formula:- in which R has the same significance as in claim 2, each Y represents hydrogen, amino, alkyl- or dialkyl­amino, or a nitrogen-containing heterocyclic group (with the proviso that at least one Y is a nitrogen containing substituent and Rʹ represent one or more substituents independently selected from hydrogen, alkyl, halogen, alkoxy, aryl, amino or substituted amino, or a heterocyclic group or the ring containing the substituent Rʹ is benzannelated and Rʺ represents hydrogen, alkyl, halogen, alkoxy or aryl.
Claim 7
Dependent Claim 44 words
A lens according to claim 5 in which the second heliochromic compound has the general formula:- in which R₃ and R₄ independently represent one or more substituents selected from hydrogen, lower alkyl, aryl, lower alkoxy, hydroxy, halogen, alkyl- or dialkylamino, or a heterocyclic group.
Claim 8
Dependent Claim 14 words
A lens according to claim 6 in which R₃ represents an alkoxy phenyl group.
Claim 9
Dependent Claim 24 words
A lens according to claim 6 or claim 7 in which Y is an amino or substituted amino, morpholino, piperidino, pyridino or pyrrolidino group.
Claim 10
Dependent Claim 29 words
A lens according to claim 6, 7 or 8, in which the R₃ substituent is a lower alkoxy, lower alkoxyphenyl or halogen group, and is present in the 6-position.
Claim 11
Dependent Claim 37 words
A lens according to claim 1 in which the second heliochromic compound has the general formula (III):- in which R is an alkyl group or an aryl group and Z represents an aryl group, alkyl or hydrogen.
Claim 12
Dependent Claim 38 words
A lens according to claim 10 in which each Z independently represent phenyl or a phenyl group substituted with a primary, secondary or tertiary amino group or with a heterocyclic nitrogen-containing group and R is an alkyl group.
Claim 13
Dependent Claim 90 words
A pyran compound having the general formula (IA):- in which R is lower alkyl, each Y independently represents hydrogen, amino or alkyl- or dialkylamino, or a nitrogen-containing heterocyclic group, with the proviso that not more than two groups represented by Y are hydrogen, Rʹ represent one or more substituents selected from hydrogen, alkyl, halogen, alkoxy, aryl, amino or substituted amino or a heterocyclic group and wherein the ring containing the substituent Rʹ may be benzannelated and Rʺ represents one or more substituents selected from hydrogen, alkyl, halogen, alkoxy or aryl.
Claim 14
Dependent Claim 90 words
A pyran compound having the general formula (IA):- in which R is lower alkyl, each Y independently represents hydrogen, amino or alkyl- or dialkylamino, or a nitrogen-containing heterocyclic group, with the proviso that not more than two groups represented by Y are hydrogen, Rʹ represent one or more substituents selected from hydrogen, alkyl, halogen, alkoxy, aryl, amino or substituted amino or a heterocyclic group and wherein the ring containing the substituent Rʹ may be benzannelated and Rʺ represents one or more substituents selected from hydrogen, alkyl, halogen, alkoxy or aryl.
Claim 15
Dependent Claim 48 words
A pyran compound having the general formula (II):- in which R₃ and R₄ independently represent one or more substituents selected from hydrogen, lower alkyl, aryl, lower alkoxy, hydroxy, halogen, alkyl- or dialkylamino or a heterocyclic group and Y and Rʹ have the same significance as in claim 12.
Claim 16
Dependent Claim 29 words
A pyran compound according to claim 13 in which the R₃ substituent is a lower alkoxy, lower alkoxy phenyl or a halogen group and is present in the 6-position.
Claim 17
Dependent Claim 27 words
A pyran compound according to claim 13 or 14 in which at least one of the groups represented by Y is an alkyl- or dialkyl amino group.
Claim 18
Dependent Claim 48 words
A pyran compound having the general formula:- in which R₃ and R₄ independently represent one or more substituents selected from hydrogen, lower alkyl, aryl, lower alkoxy, hydroxy, halogen, alkyl- or dialkylamino, or a heterocyclic group, R represents alkyl or aryl, and X represents hydrogen, lower alkyl or aryl.
Claim 19
Dependent Claim 48 words
A pyran compound having the general formula:- in which R₃ and R₄ independently represent one or more substituents selected from hydrogen, lower alkyl, aryl, lower alkoxy, hydroxy, halogen, alkyl- or dialkylamino, or a heterocyclic group, R represents alkyl or aryl, and X represents hydrogen, lower alkyl or aryl.
Claim 20
Dependent Claim 30 words
A pyran compound according to claim 16 wherein X represents a phenyl group having an amino or substituted amino or a nitrogen-containing heterocyclic substituent in the ortho or para position.
Claim 21
Dependent Claim 26 words
A pyran compound having the general formula (III):- in which R is an alkyl group or an aryl group and Z represents hydrogen, alkyl or aryl.
Claim 22
Dependent Claim 26 words
A pyran compound having the general formula (III):- in which R is an alkyl group or an aryl group and Z represents hydrogen, alkyl or aryl.
Claim 23
Dependent Claim 41 words
A compound according to claim 18 in which R is an alkyl group and each Z independently represents a phenyl group or a phenyl group which is substituted with a primary, secondary or tertiary amino group or a nitrogen-­containing heterocyclic group.

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