Patent US4699473A successfully refreshed from Google Patents.
US4699473A
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US
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Trifluoromethyl substituted spirooxazine photochromic dyes
Assignee: Sola International Inc
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Filing: 1985-12-02
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Granted: 1987-10-13
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Expires: 2005-12-02
Abstract
Abstract The organic photochromic composition of this invention comprises trifluoromethyl substituted spiro (indoline-2,3'-(3H) 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
US
Data Source
google_patents
Last Synchronized
2026-11-01 16:41
CPC Classifications
C; C07; C07D; C07D498/00; C07D498/02; C07D498/10; G; G03; G03C; G03C1/00; G03C1/685
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
52 words
An organic photochromic composition comprising at least one photochromic compound having the structural formula: ##STR8## 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
52 words
An organic photochromic composition comprising at least one photochromic compound having the structural formula: ##STR8## 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
70 words
An organic photochromic composition comprising: at least one photochromic compound having the structural formula: ##STR9## 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; and an ultraviolet stabilizer belonging to the class of peroxide decomposers or the class of excited state quenchers.
Claim 4
Dependent Claim
70 words
An organic photochromic composition comprising: at least one photochromic compound having the structural formula: ##STR9## 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; and an ultraviolet stabilizer belonging to the class of peroxide decomposers or the class of excited state quenchers.
Claim 5
Dependent Claim
14 words
The composition of claim 2 wherein the ultraviolet stabilizer comprises a singlet oxygen quencher.
Claim 6
Dependent Claim
21 words
The composition of claim 3 wherein the singlet oxygen quencher comprises a complex of Ni 2+ ion with an organic ligand.
Claim 7
Dependent Claim
13 words
The composition of claim 4 wherein the Ni 2+ complex comprises (2,2'-thiobis-4-(1,1,3,3-tetramethylbutyl)phenolato)(butylamine) nickel.
Claim 8
Dependent Claim
14 words
The composition of claim 4 wherein the Ni 2+ complex comprises nickel (0-ethyl(3,5-di-tert-butyl-4-hydroxybenzyl) phosphonate.
Claim 9
Dependent Claim
13 words
The composition of claim 4 wherein the Ni 2+ complex comprises nickel dibutyldithiocarbamate.
Claim 10
Dependent Claim
13 words
The composition of claim 4 wherein the Ni 2+ complex comprises bis(2,2'-thiobis-4-(1,1,3,3-tetramethylbutyl)phenolato) nickel.
Claim 11
Dependent Claim
13 words
The composition of claim 4 wherein the Ni 2+ complex comprises nickel di-isopropyldithiophosphate.
Claim 12
Dependent Claim
14 words
The composition of claim 3 wherein the singlet oxygen quencher comprises cobalt (II) di-iso-propyldithiocarbamate.
Claim 13
Dependent Claim
27 words
The composition of claims 1 or 2 wherein R 1 is methoxy or ethoxy, R 2 is hydrogen, R 3 is trifluoromethyl and R 4 is hydrogen.
Claim 14
Dependent Claim
27 words
The composition of claims 1 or 2 wherein R 1 is hydrogen, R 2 is methoxy or ethoxy, R 3 is trifluoromethyl and R 4 is hydrogen.
Claim 15
Dependent Claim
27 words
The composition of claims 1 or 2 wherein R 1 is methoxy or ethoxy, R 2 is hydrogen, R 3 is trifluoromethyl and R 4 is methyl.
Claim 16
Dependent Claim
27 words
The composition of claims 1 or 2 wherein R 1 is hydrogen, R 2 is methoxy or ethoxy, R 3 is trifluoromethyl and R 4 is methyl.
Claim 17
Dependent Claim
48 words
The composition of claims 1 or 2 wherein the photochromic compound is selected from 4-trifluoromethyl-1,3,3-trimethy-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-trifluromethyl-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-trifluoromethyl1,3,3-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), 5-trifluoromethyl-1,3,3-trimethyl-5'-ethoxy spiro (indoline-2,3'-(3H)-naphth-(2,1-b)(1,4)oxazine), and mixtures thereof.
Claim 18
Dependent Claim
61 words
A photochromic article comprising: (a) a plastic host; and (b) at least one photochromic compound incorporated into said host having the structural formula: ##STR10## 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 19
Dependent Claim
61 words
A photochromic article comprising: (a) a plastic host; and (b) at least one photochromic compound incorporated into said host having the structural formula: ##STR10## 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 20
Dependent Claim
84 words
A photochromic article comprising: (a) a plastic host; and (b) at least one photochromic compound incorporated into said host having the structural formula: ##STR11## 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; and (c) an ultraviolet stabilizer incorporated into said host belonging to the class of peroxide decomposers or the class of excited state quenchers.
Claim 21
Dependent Claim
84 words
A photochromic article comprising: (a) a plastic host; and (b) at least one photochromic compound incorporated into said host having the structural formula: ##STR11## 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; and (c) an ultraviolet stabilizer incorporated into said host belonging to the class of peroxide decomposers or the class of excited state quenchers.
Claim 22
Dependent Claim
15 words
The photochromic article of claim 17 wherein the ultraviolet stabilizer comprises a singlet oxygen quencher.
Claim 23
Dependent Claim
22 words
The photochromic article of claim 18 wherein the singlet oxygen quencher comprises a complex of Ni 2+ ion with an organic ligand.
Claim 24
Dependent Claim
15 words
The photochromic article of claim 18 wherein the singlet oxygen quencher comprises cobalt (II) di-iso-propyldithiocarbamate.
Claim 25
Dependent Claim
15 words
The photochromic article of claims 16 or 17 wherein the host is cellulose acetate butyrate.
Claim 26
Dependent Claim
14 words
The photochromic article of claims 16 or 17 wherein the host is polycarbonate resin.
Claim 27
Dependent Claim
13 words
The photochromic article of claims 16 or 17 wherein the host is polymethylmethacrylate.
Claim 28
Dependent Claim
16 words
The photochromic article of claims 16 or 17 wherein the host is diethylene glycol bis(allyl carbonate).
Claim 29
Dependent Claim
22 words
The photochromic article of claim 16 or 17 wherein the photochromic compound comprises a mixture of 4- and 6-trifluromethyl 1,3,3-trimethyl-5'-methoxy spiro (indoline-2,3'-(3H)-naphth-(2,1-b)(1,4)oxazine).
Claim 30
Dependent Claim
20 words
The photochromic article of claims 16 or 17 wherein the photochromic compound comprises a mixture of 4-and 6-trifluoromethyl-1,3,3-trimethyl-9'-methoxy spiro (indoline-2,3'-(3H)-naphth-(2,1-b)(1,4)oxazine).
Claim 31
Dependent Claim
22 words
The photochromic article of claims 16 or 17 wherein the photochromic compound comprises a mixture of 4- and 6-trifluoromethyl-1,3,3-trimethyl-5'-ethoxy spiro (indoline-2,4'-(3H)-naphth-(2,1-b)(1,4) oxazine).
Claim 32
Dependent Claim
23 words
The photochromic article of claims 16 or 17 wherein the photochromic compound comprises a mixture of 4- and 6-trifluoromethyl 1,3,3-trimethyl-9'-ethoxy spiro (indoline-2,3'-(3H)-naphth-(2,1-b)(1,4) oxazine).
Claim 33
Dependent Claim
16 words
The photochromic article of claim 16 or 17 wherein the photochromic compound comprises 5-trifluoromethyl-1,3,3-trimethyl-9'-methoxy spiro (indoline-2,3'-(3H)-naphth-(2,1-b)(1,4)oxazine).
Claim 34
Dependent Claim
36 words
The photochromic article of claims 16 or 17 wherein the photochromic compound comprises Y 1 -trifluoromethyl-Y 2 -methyl-1,3,3-trimethyl-5'-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.
Claim 35
Dependent Claim
36 words
The photochromic article of claims 16 or 17 wherein the photochromic compound comprises 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.
Claim 36
Dependent Claim
12 words
The photochromic article of claim 17 wherein the article is a lens.
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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) | 1990-10-12 | 1991-04-13 | 1991-10-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-10-12 | 1995-04-13 | 1995-10-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-10-12 | 1999-04-13 | 1999-10-13 | $7700.00 | Window Closed / Lapsed |