EP0134633A2
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EP
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Photochromic composition
Assignee: American Optical Corp
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Filing: 1984-06-20
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Granted: —
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Expires: 2004-06-20
Abstract
Abstract @ The organic photochromic composition of this invention comprises trifluoromethyl substituted spiro (indoline-2,3'-(3M napth-(2,1-b)(1,4)oxazine)(SO) dyes. This new class of (SO) photochromic compounds has a more neutral color when subjected to ultraviolet light irradiation. When used with a photochromic plastic embodiment, these (SO) compounds give the plastic embodiment a high luminous transmittance in an unactivated state, which can be darkened significantly when subjected to ultraviolet light irradiation. When an ultraviolet stabilizer is used with the photochromic compositions of this invention, the light fatigue resistance of the (SO) dye is improved and it will not hinder the photocolorability of the photochromic composition.
Inventors
- 👤 Nori Y. C. Chu
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-29 20:37
CPC Classifications
C; C07; C07D; C07D498/00; C07D498/02; C07D498/10; G; G03; G03C; G03C1/00; G03C1/685
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
51 words
An organic photochromic composition comprising at least on photochromic compound having the structural formula: wherein one of R 1 and R 2 is a lower alkoxy group and the other is hydrogen; R 3 is a trifluoromethyl group; and R 4 is hydrogen, a lower alkyl or a lower alkoxy group.
Claim 2
Dependent Claim
51 words
An organic photochromic composition comprising at least on photochromic compound having the structural formula: wherein one of R 1 and R 2 is a lower alkoxy group and the other is hydrogen; R 3 is a trifluoromethyl group; and R 4 is hydrogen, a lower alkyl or a lower alkoxy group.
Claim 3
Dependent Claim
23 words
The composition of Claim 1 including an ultraviolet stabilizer belonging to the class of peroxide decomposers or the class of excited state quenchers.
Claim 4
Dependent Claim
31 words
The composition of Claim 2 wherein the ultraviolet stabilizer comprises a singlet oxygen quencher such as cobalt (II) di-iso-propyldithiocarbamate or a complex of N i 2+ ion with an organic ligand.
Claim 5
Dependent Claim
27 words
The composition of Claim 3 wherein the N i 2+ complex comprises (2,2'-thiobis(4-1,1,3,3-tetramethylbutyl) phenolato) (butylamine) nickel; nickel (0-ethyl (3,5-di-tert-butyl-4-hydroxybenzyl)) phosphonate; nickel dibutyldithiocarbamate; bis(2,2'-thiobis-4-(1,1,3,3-tetramethylbutyl)phenolato) nickel; or nickel di-isopropyldithiophosphate.
Claim 6
Dependent Claim
29 words
The composition of any of Claims 1 to 4 wherein R 1 is methoxy or ethoxy, R 2 is hydrogen, R 3 is trifluoromethyl and R 4 is hydrogen.
Claim 7
Dependent Claim
29 words
The composition of any of Claims 1 to 4 wherein R 1 is hydrogen, R 2 is methoxy or ethoxy, R 3 is trifluoromethyl and R 4 is hydrogen.
Claim 8
Dependent Claim
29 words
The composition of any of Claims 1 to 4 wherein R 1 is methoxy or ethoxy, R 2 is hydrogen, R 3 is trifluoromethyl and R 4 is methyl.
Claim 9
Dependent Claim
28 words
The composition of any of Claims 1 to 4 wherein R is hydrogen, R 2 is methoxy or ethoxy, R 3 is trifluoromethyl and R 4 is methyl.
Claim 10
Dependent Claim
47 words
The composition of any of Claims 1 to 8 wherein the photochromic compound is selected from 4-trifluoromethyl-1,3,3-trimethyl-5'-methoxy spiro (indoline-2,3'-(3H)-naphth-(2,1-b)(1,4)oxazine), 6-trifluoromethyl-1, 3,3-trimethyl-5'-methoxy spiro (indoline-2,3'-(3H)-naphth-(2,1-b) (1,4)oxazine), 4-trifluoromthyl-1,3,3, -trimethyl-9'-methoxy spiro (indoline-2,3'-(3H)-naphth-(2,1-b)(1,4)oxazine), 6-trifluoromethyl-1,3,3-trimethyl-9'-methoxy spiro (indoline-2,3'-(3H)-naphth-(2,1-b)(1,4)oxazine), 4-trifluoromethyl-1,3,3-trimethyl-9'-ethoxy spiro (indoline-2,3'-(3H)-naphth-(2,1-b)(1,4)oxazine), 6-trifluoromethyl 1,3,3-trimethyl-9'-ethoxy spiro (indoline-2,3'-(3H)-naphth-(2,1-b)(1,4)oxazine), 4-trifluoromethyl-1,3,3-trimethyl-5'-ethoxy spiro (indoline-2,3'-(3H)-naphth-(2,1-b)(1,4)oxazine), 6-trifluoromethyl-1,3,3-trimethyl-5'-ethoxy spiro (indoline-2,3'-(3H)-naphth-(2,1-b)(1,4)oxazine), and mixtures thereof.
Claim 11
Dependent Claim
28 words
A photochromic article comprising: a) a plastic host; and b) at least one photochromic composition as claimed in any of Claims 1 to 9 incorporated into said host.
Claim 12
Dependent Claim
23 words
The photochromic article of Claim 10 wherein the host is cellulose acetate butyrate; polycarbonate resin; polmethyl methacrylate; or diethylene glycol bis (allyl carbonate).
Claim 13
Dependent Claim
127 words
The photochromic article of Claim 10 or 11 in which the photochromic compound comprises a mixture of 4- and 6-trifluoromethyl 1,3,3-trimethyl-5'methoxy spiro (indoline-2,3'-(3H)-naphth-(2,1-b)(1,4)oxazine); a mixture of 4- and 6-trifluoromethyl-1,3,3-trimethyl-9'-methoxy spiro tindoline-2,3'-(3H)-naphth-(2,1-b)(1,4) oxazine); a mixture of 4- and 6-trifluoromethyl-1,3,3-trimethyl-5'-ethoxy spiro (indoline-2,3'-(3H)-naphth-(2,1-b)(1,4) oxazine); a mixture of 4- and 6-trifluoromethyl 1,3,3-trimethyl-9'-ethoxy spiro (indoline-2,3'-(3H)-naphth-(2,1-b)11,4)oxazine); 5-trifluoromethyl-1,3,3-trimethyl-9'-methoxy spiro tindoline-2,3'-(3H)-naphth-(2,1-b)(1,4)oxazine); Y 1 -triofluoromethyl-Y 2 - methyl- 1,3,3-trimethyl-5'-methoxy spiro (indoline-2,3'-(3 H )-naphth (2,1-b)(1,4) oxazine), wherein Y 1 and Y 2 indicates attachment at the 4, 5, 6, or 7 position; or Y 1 -trifluoromethyl-Y 2 -methyl- 1,3,3-trimethyl-9'-methoxy spiro (indoline-2,3'-(3H)-naphth (2,1-b)(1,4) oxazine), wherein Y 1 and Y 2 indicates attachment at the 4, 5, 6 or 7 position. 13. A photochromic article according to any of Claims 10 to 12 in the form of a lens.
References Cited (Backward Citations)
No citation records indexed.
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