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US4220708A
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Photochromic compounds
Assignee: GEC-MARONI Ltd
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Filing: 1977-10-27
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Granted: 1980-09-02
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Expires: 1997-10-27
Abstract
Abstract Photochromic compounds are disclosed which are 3-furyl or 3-thienyl alkylidene succinic anhydrides or the corresponding succinimides. The compounds undergo reversible photocyclization on exposure to U.V. light in high yield and their cyclic forms are deeply colored making them suitable for a wide range of recording and display devices.
Inventors
- 👤 Harold G. Heller
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 23:19
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/54; G; G03; G03C; G03C1/00; G03C1/72; G03C1/73; Y; Y10; Y10S; Y10S428/00; Y10S428/919
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
94 words
A photochromic compound of the general formula: ##STR16## wherein X represents oxygen or ≧NR 6 , R 6 being hydrogen or an alkyl, aryl or aralkyl group; R represents an alkyl or aryl group; A represents a 3-furyl, 3-thienyl, 3-benzofuryl or 3-benzothienyl group; and B represents an adamantylidene group or the grouping ##STR17## in which R 2 and R 3 independently represent an alkyl, aryl, or a heterocyclic group containing a furyl or thienyl ring or one of R 2 and R 3 represents hydrogen and the other represents an alkyl or aryl group.
Claim 2
Dependent Claim
94 words
A photochromic compound of the general formula: ##STR16## wherein X represents oxygen or ≧NR 6 , R 6 being hydrogen or an alkyl, aryl or aralkyl group; R represents an alkyl or aryl group; A represents a 3-furyl, 3-thienyl, 3-benzofuryl or 3-benzothienyl group; and B represents an adamantylidene group or the grouping ##STR17## in which R 2 and R 3 independently represent an alkyl, aryl, or a heterocyclic group containing a furyl or thienyl ring or one of R 2 and R 3 represents hydrogen and the other represents an alkyl or aryl group.
Claim 3
Dependent Claim
15 words
The compound of claim 1, wherein R represents a lower alkyl, phenyl or naphthyl group.
Claim 4
Dependent Claim
31 words
The compound of claim 2, wherein the phenyl or naphthyl group is substituted with one or more substituent groups selected from the group consisting of alkyl, cycloalkyl, alkoxy and alkaryl groups.
Claim 5
Dependent Claim
19 words
The compound of claim 2, wherein at least one of R 2 and R 3 is alkyl or aryl.
Claim 6
Dependent Claim
96 words
A photochromic compound having the general formula: ##STR18## wherein X represents oxygen or >NR 6 , R 6 being hydrogen or an alkyl, cycloalkyl, aryl or aralkyl group; R represents an alkyl or aryl group; R 2 and R 3 independently represent an alkyl or aryl group or one of R 2 and R 3 represents hydrogen and the other represents an alkyl or aryl group; E represents oxygen or sulphur; R 4 represents hydrogen or an alkyl, aryl or aralkyl group; and each Y is independently selected from hydrogen, halogen, alkyl, aryl, or aralkyl groups.
Claim 7
Dependent Claim
96 words
A photochromic compound having the general formula: ##STR18## wherein X represents oxygen or >NR 6 , R 6 being hydrogen or an alkyl, cycloalkyl, aryl or aralkyl group; R represents an alkyl or aryl group; R 2 and R 3 independently represent an alkyl or aryl group or one of R 2 and R 3 represents hydrogen and the other represents an alkyl or aryl group; E represents oxygen or sulphur; R 4 represents hydrogen or an alkyl, aryl or aralkyl group; and each Y is independently selected from hydrogen, halogen, alkyl, aryl, or aralkyl groups.
Claim 8
Dependent Claim
21 words
A compound as claimed in claim 5, wherein at least one of R 2 and R 3 is alkyl or aryl.
Claim 9
Dependent Claim
37 words
A compound as claimed in claim 5, wherein one or more of the groups R 6 , R, R 2 , R 3 , and R 4 is an alkyl group containing 1 to 18 carbon atoms.
Claim 10
Dependent Claim
22 words
A compound as claimed in claim 7, wherein said alkyl group is a lower alkyl group containing 1 to 6 carbon atoms.
Claim 11
Dependent Claim
75 words
A compound as claimed in claim 5, wherein X represents oxygen or >NR 6 , R 6 being hydrogen, lower alkyl, phenyl or benzyl; R represents lower alkyl or phenyl, Y represents hydrogen, lower alkyl or phenyl and R 4 represents hydrogen, lower alkyl, phenyl or benzyl; R 2 and R 3 are the same or different and one represents hydrogen and the other lower alkyl or phenyl or both represent lower alkyl or phenyl.
Claim 12
Dependent Claim
36 words
A compound as claimed in claim 9, wherein one or more of the phenyl groups represented by R, R 2 , R 3 , R 4 or Y are substituted with one or more ring substituents.
Claim 13
Dependent Claim
17 words
A compound as claimed in claim 10, wherein the substituents are lower alkoxy or the group ##STR19##
Claim 14
Dependent Claim
100 words
A photochromic compound having the general formula: ##STR20## wherein X represents oxygen or >NR 6 , R 6 being hydrogen or an alkyl, aryl or aralkyl group; R represents an alkyl, aryl or aralkyl group; E represents oxygen or sulphur; R 4 represents hydrogen or an alkyl, aryl or aralkyl groups; each Y is independently selected from hydrogen, halogen, alkyl, aryl, aralkyl, alkoxy, and aryloxy groups and R 2 and R 3 independently represent an alkyl aryl or aralkyl group or one of R 2 and R 3 represents hydrogen and the other represents an alkyl, aryl or aralkyl group.
Claim 15
Dependent Claim
100 words
A photochromic compound having the general formula: ##STR20## wherein X represents oxygen or >NR 6 , R 6 being hydrogen or an alkyl, aryl or aralkyl group; R represents an alkyl, aryl or aralkyl group; E represents oxygen or sulphur; R 4 represents hydrogen or an alkyl, aryl or aralkyl groups; each Y is independently selected from hydrogen, halogen, alkyl, aryl, aralkyl, alkoxy, and aryloxy groups and R 2 and R 3 independently represent an alkyl aryl or aralkyl group or one of R 2 and R 3 represents hydrogen and the other represents an alkyl, aryl or aralkyl group.
Claim 16
Independent Claim
156 words
A method of forming a temporary image on a surface using activating radiation which comprises the steps of: (a) forming a photochromic surface comprising a photochromic compound having the general formula (II) below and a support therefor, ##STR21## wherein X represents oxygen or >NR 6 , R 6 being hydrogen or an alkyl, aryl, or aralkyl group; R represents an alkyl or aryl group; A represents a 3-furyl, 3-thienyl, 3-benzofuryl or 3-benzothienyl group; B represents an adamantylidene group or the grouping ##STR22## in which R 2 and R 3 independently represent an alkyl, aryl, or a heterocyclic group containing a furyl or thienyl ring or one of R 2 and R 3 represents hydrogen and the other represents an alkyl or aryl group, and (b) irradiating the photochromic surface through an image forming means whereby areas of the surface exposed to the radiation exhibit a change of colour resulting from reversible photocyclisation of the photochromic compound.
Claim 17
Independent Claim
156 words
A method of forming a temporary image on a surface using activating radiation which comprises the steps of: (a) forming a photochromic surface comprising a photochromic compound having the general formula (II) below and a support therefor, ##STR21## wherein X represents oxygen or >NR 6 , R 6 being hydrogen or an alkyl, aryl, or aralkyl group; R represents an alkyl or aryl group; A represents a 3-furyl, 3-thienyl, 3-benzofuryl or 3-benzothienyl group; B represents an adamantylidene group or the grouping ##STR22## in which R 2 and R 3 independently represent an alkyl, aryl, or a heterocyclic group containing a furyl or thienyl ring or one of R 2 and R 3 represents hydrogen and the other represents an alkyl or aryl group, and (b) irradiating the photochromic surface through an image forming means whereby areas of the surface exposed to the radiation exhibit a change of colour resulting from reversible photocyclisation of the photochromic compound.
Claim 18
Dependent Claim
12 words
The method of claim 13, wherein the activating radiation is U.V. light.
Claim 19
Dependent Claim
24 words
The method of claim 13, wherein the photochromic surface comprises a matrix which is capable of transmitting light having said photochromic compound dispersed therein.
Claim 20
Dependent Claim
14 words
A compound as claimed in claim 1, wherein the compound is 2,5-dimethyl-3-furyl(3',5'-dimethoxyphenyl) methylene-E-benzylidenesuccinic anhydride.
Claim 21
Dependent Claim
72 words
A photochromic compound having the general formula: ##STR23## wherein: R 1 , R 2 , and R 3 , may be the same or different, and represent alkyl or aryl; R 4 represents hydrogen, alkyl, aryl, or aralkyl; and Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , and Y 6 , may be the same or different, and represent hydrogen, halogen, alkyl, aryl, or aralkyl.
Claim 22
Dependent Claim
72 words
A photochromic compound having the general formula: ##STR23## wherein: R 1 , R 2 , and R 3 , may be the same or different, and represent alkyl or aryl; R 4 represents hydrogen, alkyl, aryl, or aralkyl; and Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , and Y 6 , may be the same or different, and represent hydrogen, halogen, alkyl, aryl, or aralkyl.
Claim 23
Dependent Claim
24 words
A photochromic device which comprises a photochromic compound as defined in claim 1 in the form of a coating on a light transparent support.
Claim 24
Dependent Claim
22 words
A photochromic device which comprises a photochromic compound as defined in claim 1 dispersed in a matrix which is transparent to light.
Claim 25
Dependent Claim
29 words
A compound as claimed in claim 1, wherein R, R 2 and R 3 or R and one of R 2 and R 3 represent aryl substituted with alkyl.
Claim 26
Dependent Claim
29 words
A compound as claimed in claim 5, wherein R, R 2 and R 3 or R and one of R 2 and R 3 represent aryl substituted with alkyl.
Claim 27
Dependent Claim
27 words
The method of claim 13, wherein R, R 2 and R 3 or R and one of R 2 and R 3 represent aryl substituted with alkyl.
Claim 28
Dependent Claim
19 words
The compound of claim 17, wherein R 1 , R 2 and R 3 represent aryl substituted with alkyl.
Claim 29
Dependent Claim
22 words
The compound of claim 5, wherein Y is independently selected from alkyl or aryl and alkyl is alkoxy and aryl is aryloxy.
Claim 30
Dependent Claim
42 words
The compound of claim 17, wherein Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 may be the same or different, and represent alkyl or aryl and alkyl is alkoxy and aryl is aryloxy.
References Cited (Backward Citations)
US3660385A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-09-02 | 1984-03-03 | 1984-09-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-09-02 | 1988-03-03 | 1988-09-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-09-02 | 1992-03-03 | 1992-09-02 | $7700.00 | Window Closed / Lapsed |