Patent US5010534A successfully refreshed from Google Patents.
Patent US4668966A successfully refreshed from Google Patents.
US4668966A
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US
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Aliphatic bridged chromogenic bisquinazolines substituted with phenylamine or phenyl-containing heterobicyclic radicals
Assignee: BASF Corp
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Filing: 1985-04-11
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Granted: 1987-05-26
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Expires: 2005-04-11
Abstract
Abstract The invention relates to bisquinazolines of the formula ##STR1## wherein the ring A is unsubstituted or substituted by cyano, nitro, halogen, lower alkyl, phenyl, benzyl, lower alkoxy or lower alkoxycarbonyl, Q is an aliphatic radical with a molecular weight of 28 to 450, or is a cycloaliphatic or araliphatic radical, Y is the radical of the formula (2a) ##STR2## or of the formula ##STR3## wherein B, D, X 1 , X 2 , X 3 and Z are as hereinafter defined. These compounds are particularly suitable as colour formers in pressure-sensitive or heat-sensitive recording materials and give strong yellow or orange colours of excellent fastness to light, especially fastness to sublimation.
Inventors
- 👤 Rudolf Zink
- 👤 Ian J. Fletcher
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 18:04
CPC Classifications
B; B41; B41M; B41M5/00; B41M5/124; B41M5/132; B41M5/136; B41M5/26; B41M5/30; B41M5/323
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
333 words
A chromogenic bisquinazoline of the formula ##STR39## wherein the ring A is unsubstituted or substituted by a group selected from nitro, halogen, lower alkyl, phenyl, benzyl, lower alkoxy and lower alkoxycarbonyl; Q is an alkylene or heteroalkylene radical having 2 to 8 carbon atoms, a radical of a polyalkylene glycol having a molecular weight in the range of from 28 to 450, or a radical of the formula ##STR40## wherein m is 1 to 9 and s is 1 to 5, or is a cycloaliphatic or araliphatic radical having not more than 10 carbon atoms; Y is the radical of the formula ##STR41## wherein X 1 and X 2 , each independently of the other, is hydrogen, alkyl of not more than 12 carbon atoms, unsubstituted or substituted by a group selected from halogen, hydroxy, cyano and lower alkoxy, or are cycloalkyl having 5 to 10 carbon atoms, phenyl, benzyl, or phenyl or benzyl, each substituted by a group selected from halogen, nitro, cyano, lower alkyl, lower alkoxy and lower alkoxycarbonyl; or X 1 and X 2 , together with the nitrogen atom to which they are attached, are a 5- or 6-member N-heterocyclic radical or a heterocyclic radical which has, in addition to nitrogen, at least one additional hetero atom selected from the group consisting of nitrogen, oxygen and sulfur; X 3 is hydrogen, halogen, lower alkyl, lower alkoxy or lower alkoxycarbonyl, and Z is hydrogen or alkyl of not more than 8 carbon atoms, unsubstituted or substituted by a member selected from the group consisting of halogen, cyano and lower alkoxy, and the benzene ring B is unsubstituted or substituted by cyano, halogen, lower alkyl or lower alkoxy, and the ring D is a hydrogenated 5- or 6-membered N-heterocyclic ring system which is unsubstituted or C-substituted by one or more of the same or different members selected from the group consisting of halogen, cyano, hydroxyl, lower alkyl, lower alkoxy, C 5 -C 6 cycloalkyl, benzyl and C 3 -C 6 alkylene.
Claim 2
Dependent Claim
333 words
A chromogenic bisquinazoline of the formula ##STR39## wherein the ring A is unsubstituted or substituted by a group selected from nitro, halogen, lower alkyl, phenyl, benzyl, lower alkoxy and lower alkoxycarbonyl; Q is an alkylene or heteroalkylene radical having 2 to 8 carbon atoms, a radical of a polyalkylene glycol having a molecular weight in the range of from 28 to 450, or a radical of the formula ##STR40## wherein m is 1 to 9 and s is 1 to 5, or is a cycloaliphatic or araliphatic radical having not more than 10 carbon atoms; Y is the radical of the formula ##STR41## wherein X 1 and X 2 , each independently of the other, is hydrogen, alkyl of not more than 12 carbon atoms, unsubstituted or substituted by a group selected from halogen, hydroxy, cyano and lower alkoxy, or are cycloalkyl having 5 to 10 carbon atoms, phenyl, benzyl, or phenyl or benzyl, each substituted by a group selected from halogen, nitro, cyano, lower alkyl, lower alkoxy and lower alkoxycarbonyl; or X 1 and X 2 , together with the nitrogen atom to which they are attached, are a 5- or 6-member N-heterocyclic radical or a heterocyclic radical which has, in addition to nitrogen, at least one additional hetero atom selected from the group consisting of nitrogen, oxygen and sulfur; X 3 is hydrogen, halogen, lower alkyl, lower alkoxy or lower alkoxycarbonyl, and Z is hydrogen or alkyl of not more than 8 carbon atoms, unsubstituted or substituted by a member selected from the group consisting of halogen, cyano and lower alkoxy, and the benzene ring B is unsubstituted or substituted by cyano, halogen, lower alkyl or lower alkoxy, and the ring D is a hydrogenated 5- or 6-membered N-heterocyclic ring system which is unsubstituted or C-substituted by one or more of the same or different members selected from the group consisting of halogen, cyano, hydroxyl, lower alkyl, lower alkoxy, C 5 -C 6 cycloalkyl, benzyl and C 3 -C 6 alkylene.
Claim 3
Dependent Claim
18 words
A bisquinazoline according to claim 1, wherein Y in formula (1) is the radical of the formula (2a).
Claim 4
Dependent Claim
30 words
A bisquinazoline according to claim 2, wherein X 1 and X 2 in formula (2a) are each independently of the other lower alkyl, benzyl, phenyl, lower alkylphenyl or lower alkoxyphenyl.
Claim 5
Dependent Claim
26 words
A bisquinazoline according to claim 1, wherein Y in formula (1) is the radical of the formula (2b), wherein Z is lower alkyl, benzyl or β-cyanoethyl.
Claim 6
Dependent Claim
24 words
A bisquinazoline according to claim 1, wherein Y in formula (1) is the radical of the formula (2b), wherein the ring D is 6-membered.
Claim 7
Dependent Claim
17 words
A bisquinazoline according to claim 1, wherein Q in formula (1) is C 2 -C 5 alkylene.
Claim 8
Dependent Claim
259 words
A bisquinazoline according to claim 1, of the formula ##STR42## wherein Q i is a straight chain or branched alkylene radical of 2 to 8, carbon atoms, or is the --(CH 2 CH 2 O) m .sbsb.1 --CH 2 CH 2 -- radical, Y 1 is an aminophenyl radical of the formula ##STR43## or a 5-indolinyl radical of the formula ##STR44## a tetrahydroquinolinyl radical of the formula ##STR45## a tetrahydroquinolinyl radical of the formula ##STR46## or a benzomorpholino radical of the formula ##STR47## wherein m 1 is 1 to 3, X 4 and X 5 are each independently of the other lower alkyl, cyanolower alkyl, benzyl, phenyl, lower alkylphenyl or lower alkoxyphenyl; or X 4 and X 5 , together with the nitrogen atom to which they are attached, are pyrrolidino, piperidino or morpholino, X 6 is hydrogen, halogen, lower alkyl or lower alkoxy, Z 1 is hydrogen, C 1 -C 8 alkyl, C 2 -C 6 alkoxyalkyl, β-cyanoethyl or benzyl, T is hydrogen, halogen, lower alkyl, lower alkoxy, C 1 -C 4 acylamino or phenyl, T 1 and T 2 are each independently of the other hydrogen, halogen, hydroxy, lower alkyl or lower alkoxy, and V 1 , V 2 , V 3 and V 4 are each independently hydrogen, lower alkyl, cycloalkyl or benzyl; or (V 1 and V 2 ) or (V 3 and V 4 ) are each together alkylene, and and the ring A 1 is unsubstituted or substituted by one or two members selected from cyano, halogen, lower alkyl, phenyl and lower alkoxy.
Claim 9
Dependent Claim
19 words
A bisquinazoline according to claim 7, wherein Y 1 in formula (3) is a radical of the formula (3a).
Claim 10
Dependent Claim
25 words
A bisquinazoline according to claim 8, wherein in formula (3a) X 4 and X 5 are lower alkyl or benzyl and X 6 is hydrogen.
Claim 11
Dependent Claim
18 words
A bisquinazoline according to claim 7, wherein Q 1 in formula (3) is C 2 -C 5 alkylene.
Claim 12
Dependent Claim
16 words
A bisquinazoline according to claim 7, wherein the ring A 1 in formula (3) is unsubstituted.
Claim 13
Dependent Claim
19 words
A bisquinazoline according to claim 7, wherein Y 1 in formula (3) is the radical of the formula (3d).
Claim 14
Dependent Claim
53 words
A bisquinazoline of the formula ##STR48## wherein Q 2 is straight chain or branched C 2 -C 4 alkylene, ##STR49## X 7 and X 8 are lower alkyl or benzyl, or --NX 7 X 8 is piperidino, X 9 is hydrogen, methyl, methoxy or ethoxy, and W is hydrogen, halogen, methyl or methoxy.
Claim 15
Dependent Claim
53 words
A bisquinazoline of the formula ##STR48## wherein Q 2 is straight chain or branched C 2 -C 4 alkylene, ##STR49## X 7 and X 8 are lower alkyl or benzyl, or --NX 7 X 8 is piperidino, X 9 is hydrogen, methyl, methoxy or ethoxy, and W is hydrogen, halogen, methyl or methoxy.
Claim 16
Dependent Claim
43 words
A bisquinazoline according to claim 13, wherein in formula (5) Q 2 is C 2 -C 4 alkylene or --CH 2 CH 2 --O--CH 2 CH 2 --, X 7 and X 8 are lower alkyl, and X 9 and W are hydrogen.
Claim 17
Dependent Claim
14 words
A bisquinazoline according to claim 13, wherein Q 2 in formula (5) is ##STR50##
Claim 18
Dependent Claim
16 words
A bisquinazoline according to claim 13, wherein Q 2 in formula (5) is ethylene or propylene.
Claim 19
Dependent Claim
71 words
A bisquinazoline according to claim 1, of the formula ##STR51## wherein Q 2 is straight chain or branched C 2 -C 4 alkylene or --CH 2 --CH 2 --O--CH 2 --CH 2 --, Z 2 is C 1 -C 8 alkyl, β-cyanoethyl or benzyl, T 3 , V 5 and V 6 are each independently lower alkyl, T 4 is hydrogen or methyl, and W is hydrogen, halogen, methyl or methoxy.
Claim 20
Dependent Claim
32 words
A bisquinazoline according to claim 16, wherein in formula (4) Z 2 is lower alkyl, T 3 , V 5 and V 6 are methyl, and T 4 and W are hydrogen.
Claim 21
Dependent Claim
31 words
A pressure-sensitive or heat-sensitive recording material which comprises a support which contains, or has coated thereon as color former, at least one bisquinazoline of the formula as indicated in claim 1.
Claim 22
Dependent Claim
28 words
The pressure-sensitive recording material of claim 19, wherein the bisquinazoline is dissolved in an organic solvent, and which recording material further comprises at least one solid electron acceptor.
Claim 23
Dependent Claim
14 words
The pressure-sensitive recording material of claim 20, wherein the bisquinazoline is encapsulated in microcapsules.
Claim 24
Dependent Claim
45 words
The pressure-sensitive recording material of claim 21, wherein the encapsulated bisquinazoline is present in the form of a layer on the back of a transfer sheet and the electron acceptor is present in the form of a layer on the face of a receiving sheet.
Claim 25
Dependent Claim
19 words
The pressure-sensitive recording material of claim 19, which comprises the bisquinazoline together with one or more other color formers.
Claim 26
Dependent Claim
29 words
The heat-sensitive recording material of claim 19, which comprises in at least one layer, at least one color former, at least one electron acceptor and at least one binder.
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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) | 1990-05-25 | 1990-11-24 | 1991-05-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-05-25 | 1994-11-24 | 1995-05-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-05-25 | 1998-11-24 | 1999-05-26 | $7700.00 | Window Closed / Lapsed |