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US4909963A Expired / Lapsed US ⏱️ 0.0 years remaining

Photochromic article

Assignee: PPG Industries Ohio Inc
•
Filing: 1988-12-06
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Granted: 1990-03-20
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Expires: 2008-12-06
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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.

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