US4637698A
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Photochromic compound and articles containing the same
Assignee: PPG Industries Ohio Inc
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Filing: 1984-07-30
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Granted: 1987-01-20
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Expires: 2004-07-30
Abstract
Abstract Photochromic compounds represented by the graphic formula: ##STR1## wherein: (a) R 1 is selected from the group consisting of C 1 -C 8 alkyl, phenyl, phen(C 1 -C 4 ) alkyl, allyl and mono- and di-substituted phenyl, said substituents being selected from C 1 -C 4 alkyl and C 1 -C 5 alkoxy; (b) R 2 and R 3 are each selected from the group consisting of C 1 -C 5 alkyl, phenyl, C 1 -C 4 alkyl and C 1 -C 5 alkoxy mono- and disubstituted phenyl, benzyl or combined to form a cyclic ring selected from the group consisting of an alicyclic ring containing from 6 to 8 carbon atoms (including the spiro carbon atom), norbornyl and adamantyl, and (c) R 4 and R 5 are each selected from the group consisting of hydrogen, C 1 -C 5 alkyl, halogen, C 1 -C 5 alkoxy, nitro, cyano and C 1 -C 8 alkoxycarbonyl are described. Solvent systems which form photochromic compositions with the above compounds and articles containing the photochromic compound are described. The compound or compositions typically change from a colorless (nonexcited) or pale color, e.g., yellow, to blue after exposure to ultraviolet light.
Inventors
- 👤 Won S. Kwak
- 👤 Rodney J. Hurditch
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 22:45
CPC Classifications
C; C07; C07D; C07D498/00; C07D498/12; C07D498/20; C08; C08L; C08L101/00; G; G03; G03C; G03C1/00; G03C1/685
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
157 words
A photochromic compound represented by the following graphic formula: ##STR11## wherein: (a) R 1 is selected from the group consisting of C 1 -C 8 alkyl, phenyl, phen(C 1 -C 4 )alkyl, allyl and mono- and disubstituted phenyl, said phenyl substituents being selected from C 1 -C 4 alkyl and C 1 -C 5 alkoxy; (b) R 2 and R 3 are each selected from the group consisting of C 1 -C 5 alkyl, phenyl, C 1 -C 4 alkyl and C 1 -C 5 alkoxy mono- and disubstituted phenyl, benzyl or combine to form a cyclic ring selected from the group consisting of an alicyclic ring containing from 6 to 8 carbon atoms (including the spiro carbon atoms), norbornyl and adamantyl, and (c) R 4 and R 5 are each selected from the group consisting of hydrogen, C 1 -C 5 alkyl, halogen, C 1 -C 5 alkoxy, nitro, cyano and C 1 -C 8 alkoxycarbonyl.
Claim 2
Dependent Claim
157 words
A photochromic compound represented by the following graphic formula: ##STR11## wherein: (a) R 1 is selected from the group consisting of C 1 -C 8 alkyl, phenyl, phen(C 1 -C 4 )alkyl, allyl and mono- and disubstituted phenyl, said phenyl substituents being selected from C 1 -C 4 alkyl and C 1 -C 5 alkoxy; (b) R 2 and R 3 are each selected from the group consisting of C 1 -C 5 alkyl, phenyl, C 1 -C 4 alkyl and C 1 -C 5 alkoxy mono- and disubstituted phenyl, benzyl or combine to form a cyclic ring selected from the group consisting of an alicyclic ring containing from 6 to 8 carbon atoms (including the spiro carbon atoms), norbornyl and adamantyl, and (c) R 4 and R 5 are each selected from the group consisting of hydrogen, C 1 -C 5 alkyl, halogen, C 1 -C 5 alkoxy, nitro, cyano and C 1 -C 8 alkoxycarbonyl.
Claim 3
Dependent Claim
69 words
A photochromic compound of claim 1 wherein: (a) R 1 is selected from the group consisting of C 1 -C 4 alkyl, phenyl and benzyl, (b) R 2 and R 3 are each selected from C 1 -C 5 alkyl, (c) and R 4 and R 5 are each selected from the group consisting of hydrogen, C 1 -C 2 alkyl, chlorine, bromine, and C 1 -C 5 alkoxy.
Claim 4
Dependent Claim
25 words
A photochromic compound of claim 1 wherein R 1 , R 2 and R 3 are methyl and R 4 and R 5 are hydrogen.
Claim 5
Dependent Claim
27 words
A photochromic compound of claim 1 wherein R 1 , R 2 , and R 3 are methyl, R 4 is methoxy, and R 5 is hydrogen.
Claim 6
Dependent Claim
25 words
A photochromic compound of claim 1 wherein R 1 , R 2 , R 3 and R 4 are methyl and R 5 is chloro.
Claim 7
Dependent Claim
7 words
The compound 1,3,5,6-tetramethyl-3-ethylspiro [indoline-2,3'[3H] pyrido[3,2-f] [1,4] benzoxazine].
Claim 8
Dependent Claim
7 words
The compound 1,3,5,6-tetramethyl-3-ethylspiro [indoline-2,3'[3H] pyrido[3,2-f] [1,4] benzoxazine].
Claim 9
Dependent Claim
6 words
The compound 1,3,3,5,6-pentamethylspiro [indoline-2,3'[3H] pyrido[3,2-f][1,4] benzoxazine].
Claim 10
Dependent Claim
6 words
The compound 1,3,3,5,6-pentamethylspiro [indoline-2,3'[3H] pyrido[3,2-f][1,4] benzoxazine].
Claim 11
Dependent Claim
6 words
The compound 1,3,4,5-tetramethyl-3-ethylspiro [indoline-2,3'[3H] pyrido [3,2-f][1,4]benzoxazine].
Claim 12
Dependent Claim
6 words
The compound 1,3,4,5-tetramethyl-3-ethylspiro [indoline-2,3'[3H] pyrido [3,2-f][1,4]benzoxazine].
Claim 13
Dependent Claim
4 words
The compound 1,3,3,4,5-pentamethylspiro[indoline-2,3'[3H] pyrido[3,2-f][1,4]benzoxazine].
Claim 14
Dependent Claim
4 words
The compound 1,3,3,4,5-pentamethylspiro[indoline-2,3'[3H] pyrido[3,2-f][1,4]benzoxazine].
Claim 15
Dependent Claim
23 words
A photochromic compound of claim 1 wherein R 1 , R 2 , R 3 , R 4 and R 5 are methyl.
Claim 16
Dependent Claim
25 words
A photochromic compound of claim 1 whereub R 1 , R 2 , R 4 and R 5 are methyl and R 3 is ethyl.
Claim 17
Dependent Claim
172 words
A photochromic article comprising a solid transparent polymerized organic host material containing a photochromic amount of a photochromic compound represented by the graphic formula: ##STR12## wherein: (a) R 1 is selected from the group consisting of C 1 -C 8 alkyl, phenyl, phen(C 1 -C 4 )alkyl, allyl and mono- and disubstituted phenyl, said phenyl substituents being selected from C 1 -C 4 alkyl and C 1 -C 5 alkoxy; (b) R 2 and R 3 are each selected from the group consisting of C 1 -C 5 alkyl, phenyl, C 1 -C 4 alkyl and C 1 -C 5 alkoxy mono- and disubstituted phenyl, benzyl or combine to form a cyclic ring selected from the group consisting of an alicyclic ring containing from 6 to 8 carbon atoms (including the spiro carbon atom), norbornyl and adamantyl, and (c) R 4 and R 5 are each selected from the group consisting of hydrogen, C 1 -C 5 alkyl, halogen, C 1 -C 5 alkoxy, nitro, cyano and C 1 -C 8 alkoxycarbonyl.
Claim 18
Dependent Claim
172 words
A photochromic article comprising a solid transparent polymerized organic host material containing a photochromic amount of a photochromic compound represented by the graphic formula: ##STR12## wherein: (a) R 1 is selected from the group consisting of C 1 -C 8 alkyl, phenyl, phen(C 1 -C 4 )alkyl, allyl and mono- and disubstituted phenyl, said phenyl substituents being selected from C 1 -C 4 alkyl and C 1 -C 5 alkoxy; (b) R 2 and R 3 are each selected from the group consisting of C 1 -C 5 alkyl, phenyl, C 1 -C 4 alkyl and C 1 -C 5 alkoxy mono- and disubstituted phenyl, benzyl or combine to form a cyclic ring selected from the group consisting of an alicyclic ring containing from 6 to 8 carbon atoms (including the spiro carbon atom), norbornyl and adamantyl, and (c) R 4 and R 5 are each selected from the group consisting of hydrogen, C 1 -C 5 alkyl, halogen, C 1 -C 5 alkoxy, nitro, cyano and C 1 -C 8 alkoxycarbonyl.
Claim 19
Dependent Claim
53 words
The photochromic article of claim 12 wherein the transparent host material is selected from the group consisting essentially of polymers of polyol(allyl carbonate), copolymers of polyol(allyl carbonate) and vinyl acetate, polyacrylates, poly(alkylacrylates), cellulose acetate, cellulose triacetate, cellulose acetate propionate, cellulose acetate butyrate, poly(vinyl acetate), poly(vinyl alcohol), polycarbonate, polystyrene, poly(styrene-methylmethacrylate)copolymers, poly(styrene-acrylonitrile)copolymers, and polyvinyl butyral.
Claim 20
Dependent Claim
24 words
The photochromic article of claim 13 wherein the transparent host material is selected from poly[diethylene glycol bis(allyl carbonate)] and its copolymers with vinyl acetate.
Claim 21
Dependent Claim
81 words
The photochromic article of claim 13 wherein the photochromic compound is represented by the graphic formula: ##STR13## wherein: (a) R 1 is selected from the group consisting of C 1 -C 4 alkyl, allyl, phenyl and benzyl, (b) R 2 and R 3 are each selected from C 1 -C 5 alkyl, (c) and R 4 and R 5 are each selected from the group consisting of hydrogen, C 1 -C 2 alkyl, chlorine, bromine, and C 1 -C 5 alkoxy.
Claim 22
Dependent Claim
121 words
A photochromic article comprising a solid transparent polymerized organic host material selected from the group consisting of polycarbonate, polymers of polyol (allyl carbonate), copolymers of polyol(allyl carbonate) and vinyl acetate, polymethylmethacrylate, cellulose acetate, cellulose propionate, cellulose butyrate, cellulose acetate butyrate, polystryrene, poly(styrene-methylmethacrylate)copolymer, and poly(styrene-acrylonitrile)copolymer, containing a photochromic amount of a photochromic compound represented by the graphic formula: ##STR14## wherein: (a) R 1 is selected from the group consisting of C 1 -C 4 alkyl, phenyl and benzyl, (b) R 2 and R 3 are each selected from C 1 -C 5 alkyl, (c) and R 4 and R 5 are each selected from the group consisting of hydrogen, C 1 -C 2 alkyl, chlorine, bromine, and C 1 -C 5 alkoxy.
Claim 23
Dependent Claim
121 words
A photochromic article comprising a solid transparent polymerized organic host material selected from the group consisting of polycarbonate, polymers of polyol (allyl carbonate), copolymers of polyol(allyl carbonate) and vinyl acetate, polymethylmethacrylate, cellulose acetate, cellulose propionate, cellulose butyrate, cellulose acetate butyrate, polystryrene, poly(styrene-methylmethacrylate)copolymer, and poly(styrene-acrylonitrile)copolymer, containing a photochromic amount of a photochromic compound represented by the graphic formula: ##STR14## wherein: (a) R 1 is selected from the group consisting of C 1 -C 4 alkyl, phenyl and benzyl, (b) R 2 and R 3 are each selected from C 1 -C 5 alkyl, (c) and R 4 and R 5 are each selected from the group consisting of hydrogen, C 1 -C 2 alkyl, chlorine, bromine, and C 1 -C 5 alkoxy.
Claim 24
Dependent Claim
21 words
The photochromic article of claim 16 wherein the photochromic compound is present in amounts of from 0.05 to 10 weight percent.
Claim 25
Dependent Claim
23 words
The photochromic article of claim 17 wherein the host material is selected from poly[diethylene glycol bis(allyl carbonate)] and its copolymers with vinyl acetate.
Claim 26
Dependent Claim
35 words
The photochromic article of claim 18 wherein the photochromic compound is one wherein R 1 , R 2 , R 4 and R 5 are methyl and R 3 is selected from methyl and ethyl.
Claim 27
Dependent Claim
22 words
The photochromic article of claim 18 wherein the copolymer is from 80-90 percent diethylene glycol bis(allyl carbonate) and 10-20 percent vinyl acetate.
Claim 28
Dependent Claim
100 words
An optical photochromic element comprising a host material selected from homopolymers of a polyol(allyl carbonate) and copolymers of polyol(allyl carbonate) and vinyl acetate and a photochromic amount of a photochromic compound represented by the graphic formula: ##STR15## wherein: (a) R 1 is selected from the group consisting of C 1 -C 4 alkyl, phenyl and benzyl, (b) R 2 and R 3 are each seIected from C 1 -C 5 alkyl, (c) and R 4 and R 5 are each selected from the group consisting of hydrogen, C 1 -C 2 alkyl, chlorine, bromine, and C 1 -C 5 alkoxy.
Claim 29
Dependent Claim
100 words
An optical photochromic element comprising a host material selected from homopolymers of a polyol(allyl carbonate) and copolymers of polyol(allyl carbonate) and vinyl acetate and a photochromic amount of a photochromic compound represented by the graphic formula: ##STR15## wherein: (a) R 1 is selected from the group consisting of C 1 -C 4 alkyl, phenyl and benzyl, (b) R 2 and R 3 are each seIected from C 1 -C 5 alkyl, (c) and R 4 and R 5 are each selected from the group consisting of hydrogen, C 1 -C 2 alkyl, chlorine, bromine, and C 1 -C 5 alkoxy.
Claim 30
Dependent Claim
42 words
The optical element of claim 21 wherein the polyol(allyl carbonate) is diethylene glycol bis(allyl carbonate), the copolymer is 80-90 percent diethylene glycol bis(allyl carbonate) and 10-20 percent vinyl acetate and the amount of photochromic compound is from 0.05 to 10 weight percent.
Claim 31
Dependent Claim
35 words
The optical element of claim 21 wherein the photochromic compound is one wherein R 1 , R 2 , R 4 and R 5 are methyl and R 3 is selected from methyl and ethyl.
Claim 32
Dependent Claim
12 words
The optical element of claim 23 wherein the element is a lens.
Claim 33
Dependent Claim
20 words
The optical lens of claim 24 wherein the photochromic compound is dispersed across at least one surface of the lens.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1990-01-19 | 1990-07-21 | 1991-01-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-01-19 | 1994-07-21 | 1995-01-20 | $3760.00 | Window Closed / Lapsed |
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