Patent US4170567A successfully refreshed from Google Patents.
US4170567A
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Photochromic mercury complexes of asymmetrical diarylthiocarbazones
Assignee: Sola International Inc
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Filing: 1977-05-12
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Granted: 1979-10-09
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Expires: 1997-05-12
Abstract
Abstract Light fatigue resistant, non-orange, photochromic mercury complexes of asymmetrical diarylthiocarbazones for use in making photochromic sunglass lenses, ski goggles, and the like. The compounds comprise the class of mono and bis mercury diarylthiocarbazonates wherein one aryl group is an aryl group substituted at the ortho position with an electron withdrawing group such as CF3 and the other aryl group is different from the first and can comprise variously substituted or unsubstituted phenyl or naphthyl groups.
Inventors
- 👤 Nori Y. C. Chu
- 👤 Peter G. Piusz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 14:11
CPC Classifications
G; G02; G02C; G02C7/00; G02C7/10; G02C7/102; G02B; G02B5/00; G02B5/20; G02B5/22; G02B5/23; G02C2202/00; G02C2202/16
Claims Analysis
Total Claims: 40
Claim 1
Independent Claim
118 words
An optically clear plastic, photochromic lens containing a photochrome selected from the group consisting of photochromic, asymmetrical mercury bis complexes of diarylthiocarbazones having absorption maxima less than about 470 nm, and having the formula: ##STR9## wherein one of R 1 and R 2 is a radical selected from the group consisting of substituted and unsubstituted aryl groups and the other one of R 1 and R 2 is an aryl group substituted in the ortho position with a radical selected from the group consisting of sulfonyl, alkylsulfonyl (C 1 -C 6 ), carboxy, carboxy alkyl (C 1 -C 6 ), aldehyde, keto alkyl (C 1 -C 6 ), cyano, trifluoromethyl, trifluoromethylsulfonyl, and perfluorothioalkoxy (C 1 -C 6 ).
Claim 2
Dependent Claim
118 words
An optically clear plastic, photochromic lens containing a photochrome selected from the group consisting of photochromic, asymmetrical mercury bis complexes of diarylthiocarbazones having absorption maxima less than about 470 nm, and having the formula: ##STR9## wherein one of R 1 and R 2 is a radical selected from the group consisting of substituted and unsubstituted aryl groups and the other one of R 1 and R 2 is an aryl group substituted in the ortho position with a radical selected from the group consisting of sulfonyl, alkylsulfonyl (C 1 -C 6 ), carboxy, carboxy alkyl (C 1 -C 6 ), aldehyde, keto alkyl (C 1 -C 6 ), cyano, trifluoromethyl, trifluoromethylsulfonyl, and perfluorothioalkoxy (C 1 -C 6 ).
Claim 3
Dependent Claim
40 words
The lens as set forth in claim 1 wherein the clear plastic comprises a plastic selected from the group consisting of cellulose acetate, cellulose acetate butyrate, polymethylmethacrylate, polymethacrylate, polystyrene, allyl diglycol carbonate, other polycarbonates, copolymers thereof, and compatible mixtures thereof.
Claim 4
Dependent Claim
44 words
The lens as set forth in claim 1 wherein said other one of R 1 and R 2 is substituted with a member selected from the group consisting of alkyl (C 1 -C 6 ), halogen, alkoxy (C 1 -C 6 ), and hydrogen.
Claim 5
Dependent Claim
31 words
The lens as set forth in claim 1 wherein said other one of R 1 and R 2 is a phenyl group substituted in the ortho position with a trifluoromethyl radical.
Claim 6
Dependent Claim
127 words
The lens as set forth in claim 4 wherein said substituted or unsubstituted aryl group is selected from the group consisting of: ##STR10## wherein R 3 is a radical selected from the group consisting of hydrogen, alkyl (C 1 -C 4 ), nitro, halo, alkoxy (C 1 -C 4 ), aryloxy (C 6 -C 10 ), hydroxy, carboxy, carboxyalkyl (C 2 -C 4 ), alkoxycarbonyl C 2 -C 6 ), aryl (C 6 -C 10 ), sulfamoyl, sulfo, arylamino (C 6 -C 10 ), alkylamino (C 1 -C 4 ), amino, acyl (C 2 -C 11 ), acylamino (C 1 -C 11 ), tetralyl perfluorothio (C 1 -C 4 ), alkylthio (C 1 -C 4 ), aldehyde, keto alkyl (C 1 -C 6 ), cyano, and trifluoromethyl.
Claim 7
Dependent Claim
59 words
An optically clear plastic, photochromic lens containing a photochrome selected from the group consisting of photochromic, asymmetrical mercury bis complexes of diarylthiocarbazones having absorption maxima at about 465 nm, and having the formula: ##STR11## wherein one of R 1 and R 2 is phenyl and the other of R 1 and R 2 is (α, α, α trifluoromethyl) phenyl.
Claim 8
Dependent Claim
59 words
An optically clear plastic, photochromic lens containing a photochrome selected from the group consisting of photochromic, asymmetrical mercury bis complexes of diarylthiocarbazones having absorption maxima at about 465 nm, and having the formula: ##STR11## wherein one of R 1 and R 2 is phenyl and the other of R 1 and R 2 is (α, α, α trifluoromethyl) phenyl.
Claim 9
Dependent Claim
37 words
The lens as set forth in claim 6 wherein said plastic is selected from the group consisting of cellulose acetate, cellulose acetate butyrate, polymethylmethacrylate polymethacrylate, polystyrene, allyl diglycol carbonate, other polycarbonates, copolymers thereof, and compatible mixtures thereof.
Claim 10
Dependent Claim
140 words
An optically clear plastic, photochromic lens containing a photochrome selected from the group consisting of photochromic, asymmetrical mercury mono complexes of diarylthiocarbazones having an absorption maxima less than about 470 nm, and having the formula: ##STR12## wherein X is selected from the group consisting of halogen, alkyl (C 1 -C 10 ), and aryl (C 6 -C 12 ), wherein one of R 1 and R 2 is selected from the group consisting of substituted and unsubstituted aryl groups and the other one of R 1 and R 2 is an aryl group substituted in the ortho position with a radical selected from the group consisting of sulfonyl, alkylsulfonyl (C 1 -C 6 ), carboxy, carboxy alkyl (C 1 -C 6 ), aldehyde, keto alkyl (C 1 -C 6 ), cyano, trifluoromethyl, perfluorothioalkoxy (C 1 -C 6 ) and trifluoromethylsulfonyl.
Claim 11
Dependent Claim
140 words
An optically clear plastic, photochromic lens containing a photochrome selected from the group consisting of photochromic, asymmetrical mercury mono complexes of diarylthiocarbazones having an absorption maxima less than about 470 nm, and having the formula: ##STR12## wherein X is selected from the group consisting of halogen, alkyl (C 1 -C 10 ), and aryl (C 6 -C 12 ), wherein one of R 1 and R 2 is selected from the group consisting of substituted and unsubstituted aryl groups and the other one of R 1 and R 2 is an aryl group substituted in the ortho position with a radical selected from the group consisting of sulfonyl, alkylsulfonyl (C 1 -C 6 ), carboxy, carboxy alkyl (C 1 -C 6 ), aldehyde, keto alkyl (C 1 -C 6 ), cyano, trifluoromethyl, perfluorothioalkoxy (C 1 -C 6 ) and trifluoromethylsulfonyl.
Claim 12
Dependent Claim
40 words
The lens as set forth in claim 8 wherein the clear plastic comprises a plastic selected from the group consisting of cellulose acetate, cellulose acetate butyrate, polymethylmethacrylate, polymethacrylate, polystyrene, allyl digylcol carbonate, other polycarbonates, copolymers thereof, and compatible mixtures thereof.
Claim 13
Dependent Claim
44 words
The lens as set forth in claim 8 wherein said other one of R 1 and R 2 is substituted with a member selected from the group consisting of alkyl (C 1 -C 6 ), halogen, alkoxy (C 1 -C 6 ), and hydrogen.
Claim 14
Dependent Claim
31 words
The lens as set forth in claim 8 wherein said other one of R 1 and R 2 is a phenyl group substituted in the ortho position with a trifluoromethyl radical.
Claim 15
Dependent Claim
127 words
The lens as set forth in claim 11 wherein said substituted or unsubstituted aryl group is selected from the group consisting of: ##STR13## wherein R 3 is a radical selected from the group consisting of hydrogen, alkyl (C 1 -C 4 ), nitro, halo, alkoxy (C 1 -C 4 ), aryloxy (C 6 -C 10 ), hydroxy, carboxy, carboxyalkyl (C 2 -C 4 ), alkoxycarbonyl (C 2 -C 6 ), aryl (C 6 -C 10 ), sulfamoyl, sulfo, arylamino (C 6 -C 10 ) alkylamino (C 1 -C 4 ), amino, acyl (C 2 -C 11 ), acylamino (C 1 -C 11 ), tetralyl perfluorothio (C 1 -C 4 ), alkylthio (C 1 -C 4 ), aldehyde, keto alkyl (C 1 -C 6 ), cyano, and trifluoromethyl.
Claim 16
Dependent Claim
83 words
An optically clear plastic photochromic lens containing a photochrome selected from the group consisting of photochromic, asymmetrical mercury mono complexes of diarylthiocarbazones having absorption maxima at about 455 nm, and having the formula: ##STR14## wherein X is selected from the group consisting of halogen, alkyl (C 1 -C 10 ), and aryl (C 6 -C 12 ), and wherein one of R 1 and R 2 is phenyl and the other one of R 1 and R 2 is ortho-(α, α, α-trifluoromethyl) phenyl.
Claim 17
Dependent Claim
83 words
An optically clear plastic photochromic lens containing a photochrome selected from the group consisting of photochromic, asymmetrical mercury mono complexes of diarylthiocarbazones having absorption maxima at about 455 nm, and having the formula: ##STR14## wherein X is selected from the group consisting of halogen, alkyl (C 1 -C 10 ), and aryl (C 6 -C 12 ), and wherein one of R 1 and R 2 is phenyl and the other one of R 1 and R 2 is ortho-(α, α, α-trifluoromethyl) phenyl.
Claim 18
Dependent Claim
37 words
The lens as set forth in claim 13 wherein said plastic is selected from the group consisting of cellulose acetate, cellulose acetate butyrate, polymethylmethacrylate, polymethacrylate, polystyrene, allyl diglycol carbonate, other polycarbonates, copolymers thereof, and compatible mixtures thereof.
Claim 19
Dependent Claim
112 words
Photochromic, asymmetrical mercury bis complexes of diarylthiocarbazones useful as photochromes in sunglass lenses and ski goggles, having absorption maxima less than about 470 nm, and having the formula: ##STR15## wherein one of R 1 and R 2 is a radical selected from the group consisting of substituted and unsubstituted aryl radicals and the other one of R 1 and R 2 is an aryl group substituted in the ortho position with a radical selected from the group consisting of sulfonyl, alkylsulfonyl (C 1 -C 6 ), carboxy, carboxy alkyl (C 1 -C 6 ), aldehyde, keto alkyl (C 1 -C 6 ), cyano, trifluoromethyl, trifluoromethylsulfonyl, and perfluorothioalkoxy (C 1 -C 6 ).
Claim 20
Dependent Claim
112 words
Photochromic, asymmetrical mercury bis complexes of diarylthiocarbazones useful as photochromes in sunglass lenses and ski goggles, having absorption maxima less than about 470 nm, and having the formula: ##STR15## wherein one of R 1 and R 2 is a radical selected from the group consisting of substituted and unsubstituted aryl radicals and the other one of R 1 and R 2 is an aryl group substituted in the ortho position with a radical selected from the group consisting of sulfonyl, alkylsulfonyl (C 1 -C 6 ), carboxy, carboxy alkyl (C 1 -C 6 ), aldehyde, keto alkyl (C 1 -C 6 ), cyano, trifluoromethyl, trifluoromethylsulfonyl, and perfluorothioalkoxy (C 1 -C 6 ).
Claim 21
Dependent Claim
23 words
A complex as set forth in claim 15 dispersed in a lens comprising an optically clear plastic to form a non-orange photochromic lens.
Claim 22
Dependent Claim
37 words
The lens as set forth in claim 16 wherein the plastic is selected from the group consisting of cellulose acetate, cellulose acetate butyrate, polymethylmethacrylate, polymethacrylate, polystyrene, allyl diglycol carbonate, other polycarbonates, copolymers thereof, and compatible mixtures thereof.
Claim 23
Dependent Claim
31 words
The complexes as set forth in claim 15 wherein said other one of R 1 and R 2 is a phenyl group substituted in the ortho position with a trifluoromethyl radical.
Claim 24
Dependent Claim
122 words
The complexes as set forth in claim 18 wherein said substituted or unsubstituted aryl groups is selected from the group consisting of: ##STR16## wherein R 3 is a radical selected from the group consisting of hydrogen, alkyl (C 1 -C 4 ), nitro, halo, alkoxy (C 1 -C 4 ), aryloxy (C 6 -C 10 ), hydroxy, carboxy, carboxyalkyl (C 2 -C 4 ), alkoxycarbonyl (C 2 -C 6 ), sulfamoyl, sulfo, arylamino (C 6 -C 10 ), alkyl amino (C 1 -C 4 ), amino, acyl (C 2 -C 11 ), acylamino (C 1 -C 11 ), tetralyl perfluorothio (C 1 -C 4 ), alkylthio (C 1 -C 4 ), aldehyde, keto alkyl (C 1 -C 6 ), cyano, and trifluoromethyl.
Claim 25
Dependent Claim
44 words
The complexes as set forth in claim 15 wherein said other one of R 1 and R 2 is substituted with a member selected from the group consisting of alkyl (C 1 -C 6 ), halogen, alkoxy (C 1 -C 6 ), and hydrogen.
Claim 26
Dependent Claim
54 words
The photochromic, asymmetrical mercury bis complexes of diarylthiocarbazones useful as photochromes in sunglass lenses and ski goggles, having absorption maxima at about 465 nm, and having the formula: ##STR17## wherein one of R 1 and R 2 is phenyl and the other of R 1 and R 2 is (α, α, α trifluoromethyl) phenyl.
Claim 27
Dependent Claim
54 words
The photochromic, asymmetrical mercury bis complexes of diarylthiocarbazones useful as photochromes in sunglass lenses and ski goggles, having absorption maxima at about 465 nm, and having the formula: ##STR17## wherein one of R 1 and R 2 is phenyl and the other of R 1 and R 2 is (α, α, α trifluoromethyl) phenyl.
Claim 28
Dependent Claim
23 words
A complex as set forth in claim 21 dispersed in a lens comprising an optically clear plastic to form a non-orange photochromic lens.
Claim 29
Dependent Claim
37 words
The lens as set forth in claim 22 wherein said plastic is selected from the group consisting of cellulose acetate, cellulose acetate butyrate, polymethylmethacrylate, polymethacrylate, polystyrene, allyl diglycol carbonate, other polycarbonates, copolymers thereof, and compatible mixtures thereof.
Claim 30
Dependent Claim
136 words
The photochromic, asymmetrical mercury mono complexes of diarylthiocarbazones useful as photochromes in sunglass lenses and ski goggles, having an absorption maxima less than about 470 nm, and having the formula: ##STR18## wherein X is selected from the group consisting of halogen, alkyl (C 1 -C 10 ), and aryl (C 6 -C 12 ), wherein one of R 1 and R 2 is selected from the group consisting of substituted and unsubstituted aryl groups and the other one of R 1 and R 2 is an aryl group substituted in the ortho position with a radical selected from the group consisting of sulfonyl, alkylsulfonyl (C 1 -C 6 ), carboxy, carboxy alkyl (C 1 -C 6 ), aldehyde, keto alkyl (C 1 -C 6 ), cyano, trifluoromethyl, trifluoromethylsulfonyl, sulfonyl, and perfluorothioalkoxy (C 1 -C 6 ).
Claim 31
Dependent Claim
136 words
The photochromic, asymmetrical mercury mono complexes of diarylthiocarbazones useful as photochromes in sunglass lenses and ski goggles, having an absorption maxima less than about 470 nm, and having the formula: ##STR18## wherein X is selected from the group consisting of halogen, alkyl (C 1 -C 10 ), and aryl (C 6 -C 12 ), wherein one of R 1 and R 2 is selected from the group consisting of substituted and unsubstituted aryl groups and the other one of R 1 and R 2 is an aryl group substituted in the ortho position with a radical selected from the group consisting of sulfonyl, alkylsulfonyl (C 1 -C 6 ), carboxy, carboxy alkyl (C 1 -C 6 ), aldehyde, keto alkyl (C 1 -C 6 ), cyano, trifluoromethyl, trifluoromethylsulfonyl, sulfonyl, and perfluorothioalkoxy (C 1 -C 6 ).
Claim 32
Dependent Claim
23 words
A complex as set forth in claim 24 dispersed in a lens comprising an optically clear plastic to form a non-orange photochromic lens.
Claim 33
Dependent Claim
37 words
The lens as set forth in claim 25 wherein said plastic is selected from the group consisting of cellulose acetate, cellulose acetate butyrate, polymethylmethacrylate, polymethacrylate, polystyrene, allyl diglycol carbonate, other polycarbonates, copolymers thereof, and compatible mixtures thereof.
Claim 34
Dependent Claim
31 words
The complexes as set forth in claim 24 wherein said other one of R 1 and R 2 is a phenyl group substituted in the ortho position with a trifluoromethyl radical.
Claim 35
Dependent Claim
128 words
The complex as set forth in claim 27 wherein said substituted or unsubstituted aryl group is selected from the group consisting of: ##STR19## wherein R 3 is a radical selected from the group consisting of hydrogen, alkyl (C 1 -C 4 ), nitro, halo, alkoxy (C 1 -C 4 ), aryloxy, (C 6 -C 10 ), hydroxy carboxy, carboxyalkyl (C 2 -C 4 ), alkoxycarbonyl (C 2 -C 6 ), aryl (C 6 -C 10 ), sulfamoyl, sulfo, arylamino (C 6 -C 10 ), alkylamino (C 1 -C 4 ), amino, acyl, (C 2 -C 11 ) acylamino (C 1 -C 11 ) tetralyl perfluorothio (C 1 14 C 4 ), alkylthio (C 1 -C 4 ), aldehyde, keto alkyl (C 1 -C 6 ), cyano, and trifluoromethyl.
Claim 36
Dependent Claim
44 words
The complexes as set forth in claim 24 wherein said other one of R 1 and R 2 is substituted with a member selected from the group consisting of alkyl (C 1 -C 6 ), halogen, alkoxy (C 1 -C 6 ), and hydrogen.
Claim 37
Dependent Claim
78 words
The photochromic, asymmetrical mercury mono complexes of diarylthiocarbazones useful as photochromes in sunglass lenses and ski goggles, having absorption maxima at about 455 nm, and having the formula: ##STR20## wherein X is selected from the group consisting of halogen, alkyl (C 1 -C 10 ), and aryl (C 6 -C 12 ) and wherein one of R 1 and R 2 is phenyl and the other one of R 1 and R 2 is ortho-(α, α, α-trifluoromethyl) phenyl.
Claim 38
Dependent Claim
78 words
The photochromic, asymmetrical mercury mono complexes of diarylthiocarbazones useful as photochromes in sunglass lenses and ski goggles, having absorption maxima at about 455 nm, and having the formula: ##STR20## wherein X is selected from the group consisting of halogen, alkyl (C 1 -C 10 ), and aryl (C 6 -C 12 ) and wherein one of R 1 and R 2 is phenyl and the other one of R 1 and R 2 is ortho-(α, α, α-trifluoromethyl) phenyl.
Claim 39
Dependent Claim
23 words
The complex as set forth in claim 30 dispersed in a lens comprising an optically clear plastic to from a non-orange photochromic lens.
Claim 40
Dependent Claim
37 words
The lens as set forth in claim 31 wherein said plastic is selected from the group consisting of cellulose acetate, cellulose acetate butyrate, polymethylmethacrylate, polymethacrylate, polystyrene, allyl diglycol carbonate, other polycarbonates, copolymers thereof, and compatible mixtures thereof.
References Cited (Backward Citations)
US3519635A
Cited
US3666352A
Cited
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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) | 1982-10-08 | 1983-04-09 | 1983-10-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-10-08 | 1987-04-09 | 1987-10-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-10-08 | 1991-04-09 | 1991-10-09 | $7700.00 | Window Closed / Lapsed |