US4784474A
Expired / Lapsed
US
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Spiro-oxazine compounds and preparation thereof and photochromic shaped article
Assignee: Toray Industries Inc
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Filing: 1987-08-03
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Granted: 1988-11-15
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Expires: 2007-08-03
Abstract
Abstract A novel spiro-oxazine compound of the formula (A): ##STR1## wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 independently represent hydrogen, (C1 or 2) alkyl, halogenated (C1 or 2) alkyl, (C1 or 2) alkoxy, halogen or nitro, R is unsubstituted or substituted phenyl or naphthyl, and n is 1 to 5. The spiro-oxazine compound is prepared by reacting a precursor of the spiro-oxazine compound of the formula (A), which has a substituent of the formula: --(CH 2 ) n R in the nitrogen atom of the indoline nucleus, with an α-nitroso-β-naphthol. The spiro-oxazine compound is valuable as a photochromic material and exhibits enhanced fatigue resistance in photocolorability.
Inventors
- 👤 Shinichi Yamamoto
- 👤 Takashi Taniguchi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 06:26
CPC Classifications
C; C07; C07D; C07D498/00; C07D498/02; C07D498/10; G; G03; G03C; G03C1/00; G03C1/685
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
101 words
A spiro-oxazine compound represented by the following general formula (A): ##STR9## wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 independently represent a hydrogen atom or a substituent selected from the group consisting of an alkyl group having 1 or 2 carbon atoms, a halogenated alkyl group having 1 or 2 carbon atoms, an alkoxy group having 1 or 2 carbon atoms, a halogen atom and a nitro group, R represents an unsubstituted or substituted phenyl or naphthyl group, and n is an integer of from 1 to 5.
Claim 2
Dependent Claim
101 words
A spiro-oxazine compound represented by the following general formula (A): ##STR9## wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 independently represent a hydrogen atom or a substituent selected from the group consisting of an alkyl group having 1 or 2 carbon atoms, a halogenated alkyl group having 1 or 2 carbon atoms, an alkoxy group having 1 or 2 carbon atoms, a halogen atom and a nitro group, R represents an unsubstituted or substituted phenyl or naphthyl group, and n is an integer of from 1 to 5.
Claim 3
Dependent Claim
76 words
A spiro-oxazine compound according to claim 1, wherein R in the formula (A) represents a phenyl or naphthyl group, which is substituted with at least one member selected from a hydroxyl group, a lower alkoxy group, an amino group, an organic substituted amino group, an aralkoxy group, an aryloxy group, a lower alkyl group, a halogen atom, a cyano group, a carboxyl group, an alkoxycarbonyl group, an acyl group, a trihalomethyl group and a nitro group.
Claim 4
Dependent Claim
19 words
A spiro-oxazine compound according to claim 1, wherein R is a phenyl group having a substituent at the meta-position.
Claim 5
Dependent Claim
22 words
A spiro-oxazine compound according to claim 1, wherein R is a naphthyl group or a phenyl group having at least two substituents.
Claim 6
Dependent Claim
15 words
A spiro-oxazine compound according to claim 1, wherein R has at least one electron-withdrawing substituent.
Claim 7
Dependent Claim
15 words
A spiro-oxazine compound according to claim 1, wherein n in the formula (A) is 1.
Claim 8
Dependent Claim
110 words
A shaped article comprising an optically transparent material and a spiro-oxazine compound represented by the following general formula (A): ##STR10## wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 independently represent a hydrogen atom or a substituent selected from the group consisting of an alkyl group having 1 or 2 carbon atoms, a halogenated alkyl group having 1 or 2 carbon atoms, an alkoxy group having 1 or 2 carbon atoms, a halogen atom and a nitro group, R represents an unsubstituted or substituted phenyl or naphthyl group, and n is an integer of from 1 to 5.
Claim 9
Dependent Claim
110 words
A shaped article comprising an optically transparent material and a spiro-oxazine compound represented by the following general formula (A): ##STR10## wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 independently represent a hydrogen atom or a substituent selected from the group consisting of an alkyl group having 1 or 2 carbon atoms, a halogenated alkyl group having 1 or 2 carbon atoms, an alkoxy group having 1 or 2 carbon atoms, a halogen atom and a nitro group, R represents an unsubstituted or substituted phenyl or naphthyl group, and n is an integer of from 1 to 5.
Claim 10
Dependent Claim
14 words
A shaped article according to claim 7, wherein the shaped article is a lens.
Claim 11
Dependent Claim
20 words
A shaped article according to claim 7, wherein the spiro-oxazine compound is substantially uniformly contained in the optically transparent material.
Claim 12
Dependent Claim
25 words
A shaped article according to claim 7, wherein a coating comprising the spiro-oxazine compound and an optically transparent resin is formed on a shaped article.
Claim 13
Dependent Claim
15 words
A shaped article according to claim 10, wherein the optically transparent resin is a polyorganosiloxane.
Claim 14
Dependent Claim
13 words
A spiro-oxazine compound according to claim 1 wherein n is greater than 1.
Claim 15
Dependent Claim
13 words
A shaped article according to claim 7 wherein n is greater than 1.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-11-15 | 1992-05-16 | 1992-11-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-11-15 | 1996-05-16 | 1996-11-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-11-15 | 2000-05-16 | 2000-11-15 | $7700.00 | Window Closed / Lapsed |