US4189171A
Expired / Lapsed
US
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Marking systems containing 3-aryl-3-heterylphthalides and 3,3-bis(heteryl)phthalides
Assignee: HD ACQUISITION CORP A CORP OF DE
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Filing: 1978-01-11
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Granted: 1980-02-19
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Expires: 1998-01-11
Abstract
Abstract 3-Aryl-3-indolylphthalides, 3-aryl-3-pyrrolylphthalides and 3-aryl-3-carbazolylphthalides prepared by interaction of the appropriate 2-(heteroaryl)carbonylbenzoic acid and the appropriate phenylamine, and 3,3-bis(indolyl)phthalides prepared by the interaction of the appropriate 2-(indolyl)carbonylbenzoic acid and the appropriate indole are useful as color formers in pressure-sensitive carbonless duplicating systems, thermal marking systems and hectographic copying systems.
Inventors
- 👤 Nathan N. Crounse
- 👤 Paul J. Schmidt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 20:46
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/30; C07D207/32; C07D207/33; C07D207/333; B; B41; B41M; B41M5/00; B41M5/025; B41M5/0253; B41M5/124; B41M5/132; B41M5/136; B41M5/145; C07D209/00; C07D209/02; C07D209/04; C07D209/10; C07D209/12; C07D209/56; C07D209/80; C07D209/82; C07D209/86; Y; Y10; Y10S; Y10S428/00; Y10S428/913; Y10S428/914
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
408 words
A pressure-sensitive carbonless duplicating system or thermal marking system containing as a color-forming substance a 3-X-3-Z-4-R°-5-R 1 -6-R 2 -7-R 3 -phthalide of the formula ##STR29## wherein: R°, R 1 , R 2 and R 3 each represent hydrogen or halo or when R°, R 3 and one of R 1 and R 2 are each hydrogen, the other of R 1 and R 2 represents ##STR30## in which B represents -OY or ##STR31## wherein Y is hydrogen, an alkali metal cation, an ammonium cation, a C 1 to C 18 mono-, di- or trialkylammonium cation, C 1 to C 18 alkyl, C 2 to C 18 alkenyl, benzyl or benzyl substituted in the benzene ring thereof by C 1 to C 12 alkyl, halo or C 1 to C 8 alkoxy; Y' is hydrogen or C 1 to C 18 alkyl; Y" is hydrogen, C 1 to C 18 alkyl or C 4 to C 12 N,N-dialkylaminoalkyl; X represents a monovalent moiety selected from the class having the formulas ##STR32## Z represents a monovalent moiety selected from the class having the formulas ##STR33## in which R represents non-tertiary C 1 to C 4 alkyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C 1 to C 3 alkyl, R 4 represents acetamido, dialkylamino in which alkyl is non-tertiary C 1 to C 4 alkyl, and when one of R 1 or R 2 represents said ##STR34## R 4 further represents hydrogen, C 1 to C 3 alkyl, C 1 to C 4 alkoxy or halo, R 5 and R 5' represent hydrogen, C 1 to C 3 alkyl or phenyl, R 6 and R 6' represent hydrogen, C 1 to C 18 alkyl, C 2 to C 4 alkenyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C 1 to C 3 alkyl, R 7 and R 8 represent hydrogen, C 1 to C 3 alkyl or phenyl, and Y 1 and Y 1' represent one or two of hydrogen, C 1 to C 3 alkyl, C 1 to C 3 alkoxy, halo or nitro with the provisos (i) that X and Z can both simultaneously represent monovalent indolyl moieties only when one of R 1 and R 2 represents said ##STR35## and (ii) X represents a pyrrolyl or a carbazolyl moiety only when Z represents a 2-R 4 -4-N(R) 2 -phenyl moiety.
Claim 2
Dependent Claim
408 words
A pressure-sensitive carbonless duplicating system or thermal marking system containing as a color-forming substance a 3-X-3-Z-4-R°-5-R 1 -6-R 2 -7-R 3 -phthalide of the formula ##STR29## wherein: R°, R 1 , R 2 and R 3 each represent hydrogen or halo or when R°, R 3 and one of R 1 and R 2 are each hydrogen, the other of R 1 and R 2 represents ##STR30## in which B represents -OY or ##STR31## wherein Y is hydrogen, an alkali metal cation, an ammonium cation, a C 1 to C 18 mono-, di- or trialkylammonium cation, C 1 to C 18 alkyl, C 2 to C 18 alkenyl, benzyl or benzyl substituted in the benzene ring thereof by C 1 to C 12 alkyl, halo or C 1 to C 8 alkoxy; Y' is hydrogen or C 1 to C 18 alkyl; Y" is hydrogen, C 1 to C 18 alkyl or C 4 to C 12 N,N-dialkylaminoalkyl; X represents a monovalent moiety selected from the class having the formulas ##STR32## Z represents a monovalent moiety selected from the class having the formulas ##STR33## in which R represents non-tertiary C 1 to C 4 alkyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C 1 to C 3 alkyl, R 4 represents acetamido, dialkylamino in which alkyl is non-tertiary C 1 to C 4 alkyl, and when one of R 1 or R 2 represents said ##STR34## R 4 further represents hydrogen, C 1 to C 3 alkyl, C 1 to C 4 alkoxy or halo, R 5 and R 5' represent hydrogen, C 1 to C 3 alkyl or phenyl, R 6 and R 6' represent hydrogen, C 1 to C 18 alkyl, C 2 to C 4 alkenyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C 1 to C 3 alkyl, R 7 and R 8 represent hydrogen, C 1 to C 3 alkyl or phenyl, and Y 1 and Y 1' represent one or two of hydrogen, C 1 to C 3 alkyl, C 1 to C 3 alkoxy, halo or nitro with the provisos (i) that X and Z can both simultaneously represent monovalent indolyl moieties only when one of R 1 and R 2 represents said ##STR35## and (ii) X represents a pyrrolyl or a carbazolyl moiety only when Z represents a 2-R 4 -4-N(R) 2 -phenyl moiety.
Claim 3
Dependent Claim
31 words
A pressure-sensitive carbonless duplicating system according to claim 1 comprising a support sheet coated on one side with a layer of pressure-rupturable microcapsules containing a liquid solution of the color-forming substance.
Claim 4
Dependent Claim
49 words
A thermal marking system according to claim 1 comprising a support sheet coated on one side with a layer containing a mixture of the color-forming substance and an acidic developer arranged such that application of heat will produce a mark-forming reaction between the color-forming substance and the acidic developer.
Claim 5
Dependent Claim
73 words
A hectographic copying system comprising a support sheet coated on one side with a layer containing a color-forming substance comprising a compound according to claim 1 wherein R°, R 3 and one of R 1 and R 2 are each hydrogen, the other of R 1 and R 2 represents ##STR36## wherein Y is an alkali metal cation, an ammonium cation or a C 1 to C 18 mono-, di- or trialkylammonium cation.
Claim 6
Dependent Claim
68 words
A pressure-sensitive carbonless duplicating system or thermal marking system according to claim 1 containing as the color-forming substance a 3-[2-R 4 -4-N(R) 2 -phenyl]-3-[(1-R 6 -2-R 5 -5/6-Y 1 )-3-indolyl]-4-R°-5-R 1 -6-R 2 -7-R 3 -phthalide wherein R, R°, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and Y 1 have the same respective meanings given in claim 1.
Claim 7
Dependent Claim
19 words
A pressure-sensitive carbonless duplicating system or thermal marking system according to claim 5 containing as a color-forming substance 3-[2,4-bis(dimethylamino)phenyl]-3-(1-ethyl-2-methy-3-indolyl)phthalide.
Claim 8
Dependent Claim
19 words
A pressure-sensitive carbonless duplicating system or thermal marking system according to claim 5 containing as a color-forming substance 3-[2,4-bis(diethylamino)phenyl]-3-(1-ethyl-2-methyl-3-indolyl)phthalide.
Claim 9
Dependent Claim
19 words
A pressure-sensitive carbonless duplicating system or thermal marking system according to claim 5 containing as a color-forming substance 3-[2,4-bis(dimethylamino)phenyl]-3-(1-ethyl-2-methyl-3-indolyl)-4,5,6,7-tetrachlorophthalide.
Claim 10
Dependent Claim
19 words
A pressure-sensitive carbonless duplicating system or thermal marking system according to claim 5 containing as a color-forming substance 3-(2-ethoxy-4-diethylaminophenyl)-3-(1-ethyl-2-methyl-3-indolyl)-5/6-ethoxycarbonylphthalide.
Claim 11
Dependent Claim
19 words
A pressure-sensitive carbonless duplicating system or thermal marking system according to claim 5 containing as a color-forming substance 3-(2-ethoxy-4-diethylaminophenyl)-3-(1-ethyl-2-methyl-3-indolyl)-5/6-hexadecyloxycarbonylphthalide.
Claim 12
Dependent Claim
75 words
A pressure-sensitive carbonless duplicating system or thermal marking system according to claim 1 containing as the color-forming substance a 3-[(1-R 6 -2-R 5 -5/6-Y 1 )-3-indolyl]-3-[(1-R 6' -2-R 5' -5/6-Y 1' -3-indolyl]-4-R°-5-R 1 -6-R 2 -7-R 3 -phthalide wherein R°, R 1 , R 2 , R 3 , R 5 , R 6 , R 5' , R 6' , Y 1 and Y 1' have the same respective meanings given in claim 51.
Claim 13
Dependent Claim
19 words
A pressure-sensitive carbonless duplicating system or thermal marking system according to claim 11 containing as the color-forming substance 3,3-bis(1-ethyl-2-methyl-3-indolyl)-5/6-methoxycarbonylphthalide.
Claim 14
Dependent Claim
19 words
A pressure-sensitive carbonless duplicating system or thermal marking system according to claim 11 containing as the color-forming substance 3,3-bis(1-ethyl-2-methyl-3-indolyl)-5/6-n-octyloxycarbonylphthalide.
Claim 15
Dependent Claim
19 words
A pressure-sensitive carbonless duplicating system or thermal marking system according to claim 11 containing as the color-forming substance 3,3-bis(1-ethyl-2-methyl-3-indolyl)-5/6-n-hexadecyloxycarbonylphthalide.
Claim 16
Dependent Claim
222 words
A pressure-sensitive carbonless duplicating system or thermal marking system containing as a color-forming substance a 3-X-3-Z-4-R°-5-R 1 -6-R 2 -7-R 3 -phthalide of the formula ##STR37## wherein: R°, R 3 and one of R 1 and R 2 are each hydrogen, the other of R 1 and R 2 represents nitro, amino, acetamido or dialkylamino wherein alkyl is non-tertiary C 1 to C 4 alkyl; X represents a monovalent moiety selected from the class having the formulas ##STR38## Z represents a monovalent moiety having the formula ##STR39## in which R represents non-tertiary C 1 to C 4 alkyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C 1 to C 3 alkyl, R 4 represents dialkylamino in which alkyl is non-tertiary C 1 to C 4 alkyl, R 5 represents hydrogen, C 1 to C 3 alkyl or phenyl, R 6 represents hydrogen, C 1 to C 18 alkyl, C 2 to C 4 alkenyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C 1 to C 3 alkyl, R 7 and R 8 represent hydrogen, C 1 to C 3 alkyl or phenyl, and Y 1 represents one or two of hydrogen, C 1 to C 3 alkyl, C 1 to C 3 alkoxy, halo or nitro.
Claim 17
Dependent Claim
222 words
A pressure-sensitive carbonless duplicating system or thermal marking system containing as a color-forming substance a 3-X-3-Z-4-R°-5-R 1 -6-R 2 -7-R 3 -phthalide of the formula ##STR37## wherein: R°, R 3 and one of R 1 and R 2 are each hydrogen, the other of R 1 and R 2 represents nitro, amino, acetamido or dialkylamino wherein alkyl is non-tertiary C 1 to C 4 alkyl; X represents a monovalent moiety selected from the class having the formulas ##STR38## Z represents a monovalent moiety having the formula ##STR39## in which R represents non-tertiary C 1 to C 4 alkyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C 1 to C 3 alkyl, R 4 represents dialkylamino in which alkyl is non-tertiary C 1 to C 4 alkyl, R 5 represents hydrogen, C 1 to C 3 alkyl or phenyl, R 6 represents hydrogen, C 1 to C 18 alkyl, C 2 to C 4 alkenyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C 1 to C 3 alkyl, R 7 and R 8 represent hydrogen, C 1 to C 3 alkyl or phenyl, and Y 1 represents one or two of hydrogen, C 1 to C 3 alkyl, C 1 to C 3 alkoxy, halo or nitro.
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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) | 1983-02-18 | 1983-08-20 | 1984-02-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-02-18 | 1987-08-20 | 1988-02-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-02-18 | 1991-08-20 | 1992-02-19 | $7700.00 | Window Closed / Lapsed |