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Patent US4124592A successfully refreshed from Google Patents.
US4124592A
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Bis-indolyl phthalides and naphthalides
Assignee: Polaroid Corp
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Filing: 1973-10-23
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Granted: 1978-11-07
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Expires: 1993-10-23
Abstract
Abstract This invention relates to indole phthalein indicator dyes including phthalides and naphthalides wherein one of the indol-3-yl radicals is substituted with a hydrogen-bonding group on a carbon atom adjacent to the nitrogen atom of the indole ring. In a preferred embodiment, one of the indol-3-yl radicals is substituted with a hydrogen-bonding group and the other indol-3-yl radical is substituted with a hydrogen-bonding group or with an electron-withdrawing group. These indicator dyes, especially those of the preferred embodiment, possess a relatively high pKa and a relatively broad absorption spectrum in the visible range.
Inventors
- 👤 Stanley M. Bloom
- 👤 Alan L. Borror
- 👤 Paul S. Huyffer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 23:54
CPC Classifications
C; C09; C09B; C09B11/00; C09B11/04; C09B11/06; C09B11/08; C09B11/26
Claims Analysis
Total Claims: 48
Claim 1
Independent Claim
209 words
A compound of the formula: ##STR25## wherein one of R 1 and R 2 is a hydrogen-bonding group selected from carboxy, --NHSO 2 R'" wherein R"' is selected from alkyl having 1 to 20 carbon atoms, phenyl, naphthyl, phenyl-substituted alkyl having up to 18 carbon atoms and alkyl-substituted phenyl having up to 18 carbon atoms, --SO 2 NHR"" wherein R"" has the same meaning as given for R'" and o-hydroxyphenyl, said o-hydroxyphenyl being unsubstituted or substituted in one of the 4- or 5-positions with alkoxy containing 1 to 12 carbon atoms, and the other is hydrogen; B is an indol-3-yl radical, ##STR26## wherein R 6 and R 7 each are selected from hydrogen, methoxy, carboxy, --NHSO 2 R'" wherein R'" has the same meaning given above, --SO 2 NHR"" wherein R"" has the same meaning given above and o-hydroxyphenyl, said o-hydroxyphenyl being unsubstitued or substituted in one of the 4- or 5-positions with alkoxy containing 1 to 12 carbon atoms, at least one of R 6 and R 7 being hydrogen; R 8 is selected from hydrogen, carboxy, cyano, halo, and alkoxy having 1 to 12 carbon atoms; and X represents the atoms necessary to complete a ring-closing moiety selected from phthalide and naphthalide, said ring-closing moiety being unsubstituted.
Claim 2
Dependent Claim
209 words
A compound of the formula: ##STR25## wherein one of R 1 and R 2 is a hydrogen-bonding group selected from carboxy, --NHSO 2 R'" wherein R"' is selected from alkyl having 1 to 20 carbon atoms, phenyl, naphthyl, phenyl-substituted alkyl having up to 18 carbon atoms and alkyl-substituted phenyl having up to 18 carbon atoms, --SO 2 NHR"" wherein R"" has the same meaning as given for R'" and o-hydroxyphenyl, said o-hydroxyphenyl being unsubstituted or substituted in one of the 4- or 5-positions with alkoxy containing 1 to 12 carbon atoms, and the other is hydrogen; B is an indol-3-yl radical, ##STR26## wherein R 6 and R 7 each are selected from hydrogen, methoxy, carboxy, --NHSO 2 R'" wherein R'" has the same meaning given above, --SO 2 NHR"" wherein R"" has the same meaning given above and o-hydroxyphenyl, said o-hydroxyphenyl being unsubstitued or substituted in one of the 4- or 5-positions with alkoxy containing 1 to 12 carbon atoms, at least one of R 6 and R 7 being hydrogen; R 8 is selected from hydrogen, carboxy, cyano, halo, and alkoxy having 1 to 12 carbon atoms; and X represents the atoms necessary to complete a ring-closing moiety selected from phthalide and naphthalide, said ring-closing moiety being unsubstituted.
Claim 3
Dependent Claim
19 words
A compound as defined in claim 1 wherein R 1 is a hydrogen-bonding group and R 2 is hydrogen.
Claim 4
Dependent Claim
19 words
A compound as defined in claim 1 wherein R 2 is a hydrogen-bonding group and R 1 is hydrogen.
Claim 5
Dependent Claim
11 words
A compound as defined in claim 1 wherein X represents phthalide.
Claim 6
Dependent Claim
11 words
A compound as defined in claim 1 wherein X represents naphthalide.
Claim 7
Dependent Claim
20 words
A compound as defined in claim 4 wherein R 1 is hydrogen; R 2 is o-hydroxyphenyl and X is phthalide.
Claim 8
Dependent Claim
20 words
A compound as defined in claim 6 wherein said R 6 , R 7 and R 8 each are hydrogen.
Claim 9
Dependent Claim
21 words
A compound as defined in claim 6 wherein R 6 and R 7 each are hydrogen and R 8 is alkoxy.
Claim 10
Dependent Claim
204 words
A compound of the formula ##STR27## wherein one of R 1 and R 2 is a hydrogen-bonding group selected from carboxy, --NHSO 2 R'" wherein R'" is selected from alkyl having 1 to 20 carbon atoms, phenyl, naphthyl, phenyl-substituted alkyl having up to 18 carbon atoms and alkyl-substituted phenyl having up to 18 carbon atoms, --SO 2 NHR"" wherein R"" has the same meaning as R'" and o-hydroxyphenyl, said o-hydroxyphenyl being unsubstituted or substituted in one of the 4- or 5-positions with alkoxy containing 1 to 12 carbon atoms and the other is hydrogen; B' is a radical selected from (1) ##STR28## wherein R 3 is an electron withdrawing group selected from carboxy and cyano and (2) ##STR29## wherein one of R 4 and R 5 is a hydrogen-bonding group selected from carboxy, --NHSO 2 R'" wherein R"' has the same meaning given above, --SO 2 NHR"" wherein R"" has the same meaning given above and o-hyroxyphenyl, said o-hydroxyphenyl being unsubstituted or substituted in one of the 4- or 5-positions with alkoxy containing 1 to 12 carbon atoms, and the other is hydrogen; and X represents the atoms necessary to complete a ring-closing moiety selected from phthalide and naphthalide, said ring-closing moiety being unsubstituted.
Claim 11
Dependent Claim
204 words
A compound of the formula ##STR27## wherein one of R 1 and R 2 is a hydrogen-bonding group selected from carboxy, --NHSO 2 R'" wherein R'" is selected from alkyl having 1 to 20 carbon atoms, phenyl, naphthyl, phenyl-substituted alkyl having up to 18 carbon atoms and alkyl-substituted phenyl having up to 18 carbon atoms, --SO 2 NHR"" wherein R"" has the same meaning as R'" and o-hydroxyphenyl, said o-hydroxyphenyl being unsubstituted or substituted in one of the 4- or 5-positions with alkoxy containing 1 to 12 carbon atoms and the other is hydrogen; B' is a radical selected from (1) ##STR28## wherein R 3 is an electron withdrawing group selected from carboxy and cyano and (2) ##STR29## wherein one of R 4 and R 5 is a hydrogen-bonding group selected from carboxy, --NHSO 2 R'" wherein R"' has the same meaning given above, --SO 2 NHR"" wherein R"" has the same meaning given above and o-hyroxyphenyl, said o-hydroxyphenyl being unsubstituted or substituted in one of the 4- or 5-positions with alkoxy containing 1 to 12 carbon atoms, and the other is hydrogen; and X represents the atoms necessary to complete a ring-closing moiety selected from phthalide and naphthalide, said ring-closing moiety being unsubstituted.
Claim 12
Dependent Claim
11 words
A compound as defined in claim 9 wherein X represents phthalide.
Claim 13
Dependent Claim
11 words
A compound as defined in claim 9 wherein X represents naphthalide.
Claim 14
Dependent Claim
11 words
A compound as defined in claim 9 wherein B' is ##STR30##
Claim 15
Dependent Claim
11 words
A compound as defined in claim 9 wherein B' is ##STR31##
Claim 16
Dependent Claim
19 words
A compound as defined in claim 9 wherein R 1 is hydrogen and R 2 is a hydrogen-bonding group.
Claim 17
Dependent Claim
11 words
A compound as defined in claim 14 wherein X represents phthalide.
Claim 18
Dependent Claim
12 words
A compound as defined in claim 15 wherein R 2 is o-hydroxyphenyl.
Claim 19
Dependent Claim
11 words
A compound as defined in claim 16 wherein B' is ##STR32##
Claim 20
Dependent Claim
12 words
A compound as defined in claim 17 wherein R 3 is carboxy.
Claim 21
Dependent Claim
12 words
A compound as defined in claim 17 wherein R 3 is cyano.
Claim 22
Dependent Claim
11 words
A compound as defined in claim 16 wherein B' is ##STR33##
Claim 23
Dependent Claim
19 words
A compound as defined in claim 20 wherein R 4 is a hydrogen-bonding group and R 5 is hydrogen.
Claim 24
Dependent Claim
12 words
A compound as defined in claim 21 wherein R 4 is o-hydroxyphenyl.
Claim 25
Dependent Claim
19 words
A compound as defined in claim 20 wherein R 4 is hydrogen and R 5 is a hydrogen-bonding group.
Claim 26
Dependent Claim
12 words
A compound as defined in claim 23 wherein R 5 is carboxy.
Claim 27
Dependent Claim
14 words
A compound as defined in claim 23 wherein R 5 is --NHSO 2 R.
Claim 28
Dependent Claim
14 words
A compound as defined in claim 23 wherein R 5 is --SO 2 NHR.
Claim 29
Dependent Claim
11 words
A compound as defined in claim 14 wherein X represents naphthalide.
Claim 30
Dependent Claim
12 words
A compound as defined in claim 27 wherein R 2 is o-hydroxyphenyl.
Claim 31
Dependent Claim
19 words
A compound as defined in claim 9 wherein R 1 is a hydrogen-bonding group and R 2 is hydrogen.
Claim 32
Dependent Claim
11 words
A compound as defined in claim 29 wherein X is naphthalide.
Claim 33
Dependent Claim
12 words
A compound as defined in claim 30 wherein R 1 is carboxy.
Claim 34
Dependent Claim
11 words
A compound as defined in claim 31 wherein B' is ##STR34##
Claim 35
Dependent Claim
19 words
A compound as defined in claim 32 wherein R 4 is hydrogen and R 5 is a hydrogen-bonding group.
Claim 36
Dependent Claim
12 words
A compound as defined in claim 33 wherein R 5 is carboxy.
Claim 37
Dependent Claim
14 words
A compound as defined in claim 33 wherein R 5 is --NHSO 2 R.
Claim 38
Dependent Claim
14 words
A compound as defined in claim 33 wherein R 5 is --SO 2 NHR.
Claim 39
Dependent Claim
3 words
The compound ##STR35##
Claim 40
Dependent Claim
3 words
The compound ##STR35##
Claim 41
Dependent Claim
3 words
The compound ##STR36##
Claim 42
Dependent Claim
3 words
The compound ##STR36##
Claim 43
Dependent Claim
3 words
The compound ##STR37##
Claim 44
Dependent Claim
3 words
The compound ##STR37##
Claim 45
Dependent Claim
3 words
The compound ##STR38##
Claim 46
Dependent Claim
3 words
The compound ##STR38##
Claim 47
Dependent Claim
3 words
The compound ##STR39##
Claim 48
Dependent Claim
3 words
The compound ##STR39##
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-11-06 | 1982-05-08 | 1982-11-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-11-06 | 1986-05-08 | 1986-11-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-11-06 | 1990-05-08 | 1990-11-07 | $7700.00 | Window Closed / Lapsed |