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US4259493A Expired / Lapsed US ⏱️ 0.0 years remaining

Perhalomethylcarbinol-substituted phenol and naphthol sulfamphthaleins

Assignee: Polaroid Corp
•
Filing: 1978-11-02
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Granted: 1981-03-31
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Expires: 1998-11-02
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Abstract

Abstract The present invention is concerned with novel 3,3-disubstituted-sulfam(na)phthaleins wherein one of the 3-substituents is derived from a 1-naphthol or a phenol substituted in the 2-position with a perhalomethylcarbinol group and wherein the N atom of the sulfam(na)phthalein ring is substituted with ##STR1## wherein R is alkyl or aryl or with ##STR2## wherein Y is hydrogen or an electron-withdrawing group, which compounds find utility, e.g., as pH-sensitive indicator dyes or as photographic light-screening dyes.

Inventors

  • 👤 James W. Foley

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 19:26
CPC Classifications
C; C07; C07D; C07D275/00; C07D275/04; C07D275/06

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 229 words
A compound of the formula ##STR62## wherein R 0 is perhalomethyl selected from trifluoromethyl, difluoromethyl, difluorochloromethyl, dichlorofluoromethyl, dichloromethyl and trichloromethyl; R 1 is selected from hydrogen and perhalomethyl having the same meaning given above; R 2 is hydrogen or methyl; R 3 is hydrogen, alkyl or alkoxy; R 2 and R 3 taken together represent the carbon atoms necessary to complete a fused benzene ring; R 4 and R 6 each are selected from hydrogen, alkyl, alkoxy, chloro and fluoro; R 7 is hydrogen, hydroxy, alkyl or alkoxy; R 6 and R 7 taken together represent the carbon atoms necessary to complete a fused benzene ring provided R 2 and R 3 are taken separately when R 6 and R 7 are taken together; R 5 is selected from hydrogen, hydroxy, alkyl, alkoxy, --N,N--(dialkyl)amino, --N,N--(ω-R 8 alkyl) 2 amino wherein R 8 is hydroxy or halo; --NHCOCH 3 , piperidino, pyrrolidino, N-methylpiperazino, morpholino, thiomorpholino or tetrahydro-2H,4H-1,3,6-dioxazocino; R 4 , R 5 and R 6 taken together represent the atoms necessary to complete a fused [ij]quinolizidine ring; Z is a group selected from ##STR63## wherein R is alkyl having 1 to 7 carbon atoms or phenyl and ##STR64## wherein Y is hydrogen or an electron-withdrawing group having a positive sigma value greater than 0.6 as defined by Hammett's Equation; and X represents the atoms necessary to complete 2,3-dihydrobenz[d]isothiazole-1,1-dioxide or 2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxide.
Claim 2
Dependent Claim 229 words
A compound of the formula ##STR62## wherein R 0 is perhalomethyl selected from trifluoromethyl, difluoromethyl, difluorochloromethyl, dichlorofluoromethyl, dichloromethyl and trichloromethyl; R 1 is selected from hydrogen and perhalomethyl having the same meaning given above; R 2 is hydrogen or methyl; R 3 is hydrogen, alkyl or alkoxy; R 2 and R 3 taken together represent the carbon atoms necessary to complete a fused benzene ring; R 4 and R 6 each are selected from hydrogen, alkyl, alkoxy, chloro and fluoro; R 7 is hydrogen, hydroxy, alkyl or alkoxy; R 6 and R 7 taken together represent the carbon atoms necessary to complete a fused benzene ring provided R 2 and R 3 are taken separately when R 6 and R 7 are taken together; R 5 is selected from hydrogen, hydroxy, alkyl, alkoxy, --N,N--(dialkyl)amino, --N,N--(ω-R 8 alkyl) 2 amino wherein R 8 is hydroxy or halo; --NHCOCH 3 , piperidino, pyrrolidino, N-methylpiperazino, morpholino, thiomorpholino or tetrahydro-2H,4H-1,3,6-dioxazocino; R 4 , R 5 and R 6 taken together represent the atoms necessary to complete a fused [ij]quinolizidine ring; Z is a group selected from ##STR63## wherein R is alkyl having 1 to 7 carbon atoms or phenyl and ##STR64## wherein Y is hydrogen or an electron-withdrawing group having a positive sigma value greater than 0.6 as defined by Hammett's Equation; and X represents the atoms necessary to complete 2,3-dihydrobenz[d]isothiazole-1,1-dioxide or 2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxide.
Claim 3
Dependent Claim 12 words
A compound as defined in claim 1 wherein R 1 is hydrogen.
Claim 4
Dependent Claim 12 words
A compound as defined in claim 1 wherein R 1 is perhalomethyl.
Claim 5
Dependent Claim 26 words
A compound as defined in claim 1 wherein R 2 and R 3 taken together represent the carbon atoms necessary to complete a fused benzene ring.
Claim 6
Dependent Claim 15 words
A compound as defined in claim 1 wherein R 2 and R 3 are hydrogen.
Claim 7
Dependent Claim 33 words
A compound as defined in claim 1 wherein R 4 , R 5 and R 6 taken together represent the atoms necessary to complete a fused [ij]quinolizidine ring and R 7 is hydrogen.
Claim 8
Dependent Claim 18 words
A compound as defined in claim 1 wherein R 4 , R 6 and R 7 are hydrogen.
Claim 9
Dependent Claim 12 words
A compound as defined in claim 7 wherein R 5 is --N,N--(dialkyl)amino.
Claim 10
Dependent Claim 16 words
A compound as defined in claim 7 wherein R 5 is --N,N--(ω-R 8 alkyl) 2 amino.
Claim 11
Dependent Claim 24 words
A compound as defined in claim 1 wherein R 4 and R 6 are hydrogen, R 5 is --N,N--(dialkyl)amino and R 7 is alkyl.
Claim 12
Dependent Claim 12 words
A compound as defined in claim 1 wherein R is said alkyl.
Claim 13
Dependent Claim 13 words
A compound as defined in claim 1 wherein Y is said electron-withdrawing group.
Claim 14
Dependent Claim 3 words
The compound ##STR65##
Claim 15
Dependent Claim 3 words
The compound ##STR65##
Claim 16
Dependent Claim 3 words
The compound ##STR66##
Claim 17
Dependent Claim 3 words
The compound ##STR66##

References Cited (Backward Citations)

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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) 1984-03-30 1984-09-29 1985-03-31 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-03-30 1988-09-29 1989-03-31 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-03-30 1992-09-29 1993-03-31 $7700.00 Window Closed / Lapsed

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