US4909963A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Photochromic article
Assignee: PPG Industries Ohio Inc
•
Filing: 1988-12-06
•
Granted: 1990-03-20
•
Expires: 2008-12-06
Abstract
Abstract Described are photochromic spiro(indoline)benzoxazine compounds having substituents on the benzoxazine portion of the compound, and their use in plastic hosts to impart a photochromic response thereto.
Inventors
- 👤 Won S. Kwak
- 👤 Chin-Wen Chen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 17:11
CPC Classifications
C; C07; C07D; C07D498/00; C07D498/02; C07D498/10; G; G02; G02B; G02B5/00; G02B5/20; G02B5/22; G02B5/23
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
340 words
A photochromic article comprising a polymerized organic host material and a photochromic amount of a photochromic compound represented by the graphic formula: ##STR9## wherein: (a) R 1 is selected from the group consisting of C 1 -C 8 alkyl, phenyl, phen(C 1 -C 4 )alkyl, naphth (C 1 -C 4 ) alkyl, allyl, acrylyl, methacrylyl, C 1 -C 4 acyloxy (C 2 -C 6 )alkyl, carboxy(C 2 -C 6 )alkyl, cyano(C 2 -C 6 )alkyl, hydroxy(C 2 -C 6 )alkyl, (C 2 H 4 O) m ·CH 3 , and mono- and di-substituted phenyl, said phenyl substituents being selected from C 1 -C 4 alkyl and C 1 -C 5 alkoxy, and m is a number from 1 to 6; (b) R 2 and R 3 are each selected from the group consisting of C 1 -C 5 alkyl, phenyl, and mono- and di-substituted 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, said phenyl substituents being selected from C 1 -C 4 alkyl and C 1 -C 5 alkoxy; (c) each R 4 is selected from the group consisting of C 1 -C 5 alkyl, halogen, C 1 -C 5 alkoxy, nitro, cyano, C 1 -C 4 monohaloalkyl, C 1 -C 4 polyhaloalkyl, C 1 -C 8 alkoxycarbonyl, and C 1 -C 4 acyloxy; (d) each R 5 is selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 5 alkoxy, nitro, cyano, thiocyano, C 1 -C 4 monohaloalkyl, and C 1 -C 2 polyhaloalkyl; and (e) the letters "c" and "e" are numbers of from 0 to 4 and 1 to 4 respectively, said organic host material being selected from the group consisting of polymers of polyol(allyl carbonate), polyacrylates, poly(alkylacrylates), cellulose acetate, cellulose triacetate, cellulose acetate propionate, cellulose acetate butyrate, poly(vinyl acetate), poly(vinyl alcohol), poly(vinyl chloride), poly(vinylidene chloride), polyurethane, polycarbonate, poly(ethylene terephthalate), polystyrene, poly(styrene-methylmethacrylate)copolymers, poly(styrene-acrylonitrile) copolymers, and poly(vinyl butyral).
Claim 2
Dependent Claim
340 words
A photochromic article comprising a polymerized organic host material and a photochromic amount of a photochromic compound represented by the graphic formula: ##STR9## wherein: (a) R 1 is selected from the group consisting of C 1 -C 8 alkyl, phenyl, phen(C 1 -C 4 )alkyl, naphth (C 1 -C 4 ) alkyl, allyl, acrylyl, methacrylyl, C 1 -C 4 acyloxy (C 2 -C 6 )alkyl, carboxy(C 2 -C 6 )alkyl, cyano(C 2 -C 6 )alkyl, hydroxy(C 2 -C 6 )alkyl, (C 2 H 4 O) m ·CH 3 , and mono- and di-substituted phenyl, said phenyl substituents being selected from C 1 -C 4 alkyl and C 1 -C 5 alkoxy, and m is a number from 1 to 6; (b) R 2 and R 3 are each selected from the group consisting of C 1 -C 5 alkyl, phenyl, and mono- and di-substituted 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, said phenyl substituents being selected from C 1 -C 4 alkyl and C 1 -C 5 alkoxy; (c) each R 4 is selected from the group consisting of C 1 -C 5 alkyl, halogen, C 1 -C 5 alkoxy, nitro, cyano, C 1 -C 4 monohaloalkyl, C 1 -C 4 polyhaloalkyl, C 1 -C 8 alkoxycarbonyl, and C 1 -C 4 acyloxy; (d) each R 5 is selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 5 alkoxy, nitro, cyano, thiocyano, C 1 -C 4 monohaloalkyl, and C 1 -C 2 polyhaloalkyl; and (e) the letters "c" and "e" are numbers of from 0 to 4 and 1 to 4 respectively, said organic host material being selected from the group consisting of polymers of polyol(allyl carbonate), polyacrylates, poly(alkylacrylates), cellulose acetate, cellulose triacetate, cellulose acetate propionate, cellulose acetate butyrate, poly(vinyl acetate), poly(vinyl alcohol), poly(vinyl chloride), poly(vinylidene chloride), polyurethane, polycarbonate, poly(ethylene terephthalate), polystyrene, poly(styrene-methylmethacrylate)copolymers, poly(styrene-acrylonitrile) copolymers, and poly(vinyl butyral).
Claim 3
Dependent Claim
21 words
The photochromic article of claim 1 wherein the polyol(allyl)carbonate is selected polymer from transparent poly and its copolymers with vinyl acetate.
Claim 4
Dependent Claim
190 words
The photochromic article of claim 1 wherein the photochromic compound is represented by the graphic formula: ##STR10## wherein: (a) R 1 is selected from the group consisting of C 1 -C 4 alkyl, phenyl, benzyl, naphth (C 1 -C 2 ) alkyl, carboxy (C 2 -C 4 ) alkyl, cyano (C 2 -C 4 ) alkyl, C 1 -C 4 acyloxy (C 2 -C 4 ) alkyl, hydroxy (C 2 -C 4 ) alkyl and (C 2 H 4 O) m ·CH 3 , wherein m is a number of from 1 to 3, (b) R 2 and R 3 are each selected from C 1 -C 5 alkyl, (c) each R 4 is selected from the group consisting of C 1 -C 2 alkyl, chloro, fluoro, C 1 -C 5 alkoxy and C 1 -C 2 trihaloalkyl, (d) each R 5 is selected from the group consisting of chloro, fluoro, bromo, nitro, C 1 -C 4 alkyl, C 1 -C 2 alkoxy and trifluoromethyl, and (e) the letter "c" is a number of from 0 to 2, and the letter "e" is a number of from 1 to 3.
Claim 5
Dependent Claim
193 words
A photochromic article comprising a solid transparent polymerized organic host material selected from the group consisting of polycarbonate, polymers of polyol (allyl carbonate), polymethylmethacrylate, cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, poly(vinyl acetate), poly(vinyl chloride), poly(vinylidene chloride), poly(ethylene terephthalate), poly(vinyl butyral), polystyrene, poly(styrenemethylmethacrylate)copolymer, and poly(styrene acrylonitrile)copolymer, said host material containing a photochromic amount of a photochromic compound represented by the graphic formula: ##STR11## wherein: (a) R 1 is selected from the group consisting of C 1 -C 4 alkyl, phenyl, benzyl, 1-naphthylmethyl, B-carboxyethyl, B-cyanoethyl, acetoxyethyl, hydroxyethyl and (C 2 H 4 O) 2 ·CH 3 , (b) R 2 and R 3 are each selected from C 1 -C 5 alkyl, (c) each R 4 is selected from the group consisting of C 1 -C 2 alkyl, chloro, fluoro, C 1 -C 5 alkoxy and C 1 -C 2 trihaloalkyl, (d) each R 5 is selected from the group consisting of chloro, fluoro, bromo, nitro, C 1 -C 2 alkyl, C 1 -C 2 alkoxy and trifluoromethyl, and (e) the letter "c" is a number of from 0 to 2, and the letter "e" is a number of from 1 to 3.
Claim 6
Dependent Claim
193 words
A photochromic article comprising a solid transparent polymerized organic host material selected from the group consisting of polycarbonate, polymers of polyol (allyl carbonate), polymethylmethacrylate, cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, poly(vinyl acetate), poly(vinyl chloride), poly(vinylidene chloride), poly(ethylene terephthalate), poly(vinyl butyral), polystyrene, poly(styrenemethylmethacrylate)copolymer, and poly(styrene acrylonitrile)copolymer, said host material containing a photochromic amount of a photochromic compound represented by the graphic formula: ##STR11## wherein: (a) R 1 is selected from the group consisting of C 1 -C 4 alkyl, phenyl, benzyl, 1-naphthylmethyl, B-carboxyethyl, B-cyanoethyl, acetoxyethyl, hydroxyethyl and (C 2 H 4 O) 2 ·CH 3 , (b) R 2 and R 3 are each selected from C 1 -C 5 alkyl, (c) each R 4 is selected from the group consisting of C 1 -C 2 alkyl, chloro, fluoro, C 1 -C 5 alkoxy and C 1 -C 2 trihaloalkyl, (d) each R 5 is selected from the group consisting of chloro, fluoro, bromo, nitro, C 1 -C 2 alkyl, C 1 -C 2 alkoxy and trifluoromethyl, and (e) the letter "c" is a number of from 0 to 2, and the letter "e" is a number of from 1 to 3.
Claim 7
Dependent Claim
49 words
The photochromic article of claim 4 wherein R 1 is C 1 -C 4 alkyl, R 2 and R 3 are each methyl or ethyl, each R 4 is trifluoromethyl, fluorine, chlorine, methyl, ethyl or methoxy, and each R 5 is trifluoromethyl, chloro, fluoro, methyl, ethyl, methoxy and ethoxy.
Claim 8
Dependent Claim
21 words
The photochromic article of claim 4 wherein the photochromic compound is present in amounts of from 0.05 to 10 weight percent.
Claim 9
Dependent Claim
21 words
The photochromic article of claim 6 wherein the polyol(allyl carbonate) polymer is selected from poly and its copolymers with vinyl acetate.
Claim 10
Dependent Claim
24 words
The photochromic article of claim 7 wherein the copolymer is from 80-90 weight percent diethylene glycol bis(allyl carbonate) and 10-20 weight percent vinyl acetate.
Claim 11
Dependent Claim
88 words
An article according to claim 1 wherein R 1 is a C 1 -C 4 alkyl, R 2 and R 3 are each selected from the group consisting of methyl and ethyl, each R 4 is selected from the group consisting of methyl, ethyl, fluorine and trifluoromethyl, each R 5 is selected from the group consisting of C 1 -C 4 alkyl, methoxy and ethoxy, the letter "c" is a number of from 0 to 2, and the letter "e" is a number of from 1 to 3.
Claim 12
Dependent Claim
18 words
An article according to claim 9 wherein each R 5 is methoxy and the letter "e" is 2.
Claim 13
Dependent Claim
19 words
An article according to claim 10 wherein the R 5 substituents are located at the 5 and 7 positions.
Claim 14
Dependent Claim
31 words
An article according to claim 9 wherein each R 5 substituent is selected from the group consisting of C 1 -C 4 alkyl and methoxy and the letter "e" is 3.
Claim 15
Dependent Claim
20 words
An article according to claim 12 wherein the R 5 substituents are located at the 5, 7 and 8 positions.
Claim 16
Dependent Claim
65 words
An article according to claim 3 wherein R 1 is C 1 -C 4 alkyl, R 2 and R 3 are each methyl or ethyl, each R 4 is chloro, fluoro, trifluoromethyl, methyl, ethyl or methoxy, each R 5 is chloro, fluoro, C 1 -C 4 alkyl, methoxy or ethoxy, the letter "c" is 0 to 2 and the letter "e" is 1 to 3.
Claim 17
Dependent Claim
19 words
The photochromic article of claim 4 wherein the host material is a polymer prepared from diethylene glycol bis(allyl carbonate).
Claim 18
Dependent Claim
88 words
The photochromic article of claim 15 wherein R 1 is a C 1 -C 4 alkyl, R 2 and R 3 are each selected from the group consisting of methyl and ethyl, each R 4 is selected from the group consisting of methyl, ethyl, fluorine and trifluoromethyl, each R 5 is selected from the group consisting of C 1 -C 4 alkyl, methoxy and ethoxy, the letter "c" is a number of from 0 to 2, and the letter "e" is a number of from 1 to 3.
Claim 19
Dependent Claim
18 words
The photochromic article of claim 16 wherein each R 5 is methoxy and the letter "e" is 2.
Claim 20
Dependent Claim
19 words
The photochromic article of claim 17 wherein the R 5 substituents are located at the 5 and 7 positions.
Claim 21
Dependent Claim
31 words
The photochromic article of claim 16 wherein each R 5 substituent is selected from the group consisting of C 1 -C 4 alkyl and methoxy and the letter "e" is 3.
Claim 22
Dependent Claim
20 words
The photochromic article of claim 19 wherein the R 5 substituents are located at the 5, 7 and 8 positions.
References Cited (Backward Citations)
US3407145A
Cited
US3578602A
Cited
GB1243370A
Cited
US3843550A
Cited
US3562172A
Cited
GB1227713A
Cited
DE1927849A1
Cited
US3980480A
Cited
US4215010A
Cited
US4342668A
Cited
US4289497A
Cited
US4440672A
Cited
US4637698A
Cited
US4636561A
Cited
GB2174711A
Cited
DD238611A1
Cited
US4634767A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-03-19 | 1993-09-18 | 1994-03-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-03-19 | 1997-09-18 | 1998-03-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-03-19 | 2001-09-18 | 2002-03-20 | $7700.00 | Window Closed / Lapsed |