Patent US3954803A successfully refreshed from Google Patents.
US3954803A
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Dilactone chromogenic compounds and preparation thereof
Assignee: Champion International Corp
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Filing: 1974-01-02
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Granted: 1976-05-04
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Expires: 1994-01-02
Abstract
Abstract A substantially colorless dilactone chromogenic material having the structural formula ##SPC1## And ##SPC2## Wherein R represents an alkyl group, an aryl group, an aralkyl group, an acyl group or an aroyl group; and X represents a hydrogen atom, a halogen atom, an alkyl group or a nitro group. The dilactone compounds are produced from precursor compounds that are formed by reacting pyromellitic dianhydride with a resorcinol having at least the fourth or the sixth position unsubstituted, in the presence of a dehydrating agent to form xanthyl derivatives of isophthalic and terephthalic acid. These precursors are then further reacted to form the dilactones. The dilactones are used in pressure-sensitive copy systems comprising a support bearing microcapsules containing the dilactones, alone, or in combination with other chromogenic materials.
Inventors
- 👤 David N. Vincent
- 👤 Cheng Hsiung Chang
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 17:18
CPC Classifications
B; B41; B41M; B41M5/00; B41M5/124; B41M5/132; B41M5/136; B41M5/145; C; C09; C09B; C09B11/00; C09B11/04; C09B11/06; C09B11/08
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
48 words
A chromogenous compound having a formula selected from the group consisting of ##SPC7## wherein: R represents an alkyl group, an aryl group, an aralkyl group, an acyl group or an aroyl group; and X represents a hydrogen atom, a halogen atom, an alkyl group or a nitro group.
Claim 2
Dependent Claim
48 words
A chromogenous compound having a formula selected from the group consisting of ##SPC7## wherein: R represents an alkyl group, an aryl group, an aralkyl group, an acyl group or an aroyl group; and X represents a hydrogen atom, a halogen atom, an alkyl group or a nitro group.
Claim 3
Dependent Claim
45 words
The compound of claim 1 wherein: R represents a lower alkyl group, an aryl group, a benzyl group, a lower acyl group or a benzoyl group; and X represents a hydrogen atom, a chlorine atom, a bromine atom, an alkyl group or a nitro group.
Claim 4
Dependent Claim
21 words
The compound of claim 2 wherein R is methyl and X is hydrogen, said compounds being trans 3,7-bis[3',6'-dimethoxy-9'-spiroxanthyl]pyromellitide and cis 3,5-bis[3',6'-dimethoxy-9'-spiroxanthyl]pyromellitide.
Claim 5
Dependent Claim
22 words
The compound of claim 2 wherein R is methyl and X is methyl, said compounds being trans 3,7-bis[4',5'-dimethyl-3',6'-dimethoxy-9'-spiroxanthyl]pyromellitide and cis 3,5-bis [4',5'-dimethyl-3',6'-dimethoxy-9'-spiroxanthyl]pyromellitide.
Claim 6
Dependent Claim
25 words
The compound of claim 2 wherein R is methyl and X is chlorine, said compounds being trans 3,7-bis[2',7'-dichloro-3',6'-dimethoxy-9'-spiroxanthyl]pyromellitide and cis 3,52', 7'-dichloro- 3', 6'-dimethoxy- 9'-spiroxanthyl]pyromellitide.
Claim 7
Dependent Claim
21 words
The compound of claim 2 wherein R is benzyl and X is hydrogen, said compounds being trans 3,7-bis[3',6'-dibenzyloxy-9'-spiroxanthyl]pyromellitide and cis 3,5-bis[3',6'-dibenzyloxy-9'-spiroxanthyl]pyromellitide.
Claim 8
Dependent Claim
21 words
The compound of claim 2 wherein R is acetyl and X is hydrogen, said compounds being trans 3,7-bis[3',6'-diacetoxy-9'-spiroxanthyl]pyromellitide and cis 3,5-bis[3',6'-diacetoxy-9'-spiroxanthyl]pyromellitide.
Claim 9
Dependent Claim
21 words
The compound of claim 2 wherein R is butyryl and X is hydrogen, said compounds being trans 3,7-bis[3',6'-dibutyroxy-9'-spiroxanthyl]pyromellitide and cis 3,5-bis[3',6'-dibutyroxy-9'-spiroxanthyl]pyromellitide.
Claim 10
Dependent Claim
21 words
The compound of claim 2 wherein R is benzoyl and X is hydrogen, said compounds being trans 3,7-bis[3',6'-dibenzoxy-9'-spiroxanthyl]pyromellitide and cis 3,5-bis[3',6'-dibenzoxy-9'-spiroxanthyl]pyromellitide.
Claim 11
Dependent Claim
51 words
A process which comprises reacting pyromellitic dianhydride with a resorcinol having at least the 4 or the 6 position unsubstituted in the presence of a dehydrating agent and a solvent in which said dianhydride and said resorcinol are at least partially soluble, to form xanthyl derivatives of isophthalic and terephthalic acid.
Claim 12
Dependent Claim
51 words
A process which comprises reacting pyromellitic dianhydride with a resorcinol having at least the 4 or the 6 position unsubstituted in the presence of a dehydrating agent and a solvent in which said dianhydride and said resorcinol are at least partially soluble, to form xanthyl derivatives of isophthalic and terephthalic acid.
Claim 13
Dependent Claim
20 words
The method of claim 10 wherein said solvent has a boiling point within the range of 100° to 175° C.
Claim 14
Dependent Claim
10 words
The method of claim 11 wherein said solvent is xylene.
Claim 15
Dependent Claim
13 words
The method of claim 11 wherein said reaction takes place under reflux conditions.
Claim 16
Dependent Claim
18 words
The process of claim 11 wherein the product of said process is filtered to recover an insoluble mass.
Claim 17
Dependent Claim
28 words
The process of claim 11 wherein said resorcinol has the formula ##SPC8## wherein X represents a hydrogen atom, an alkyl group, a halogen atom or a nitro group.
Claim 18
Dependent Claim
27 words
The process of claim 15 wherein the xanthyl derivatives are alkylated, and the alkylated xanthyl derivatives are subjected to saponification and acidification to provide dilactone chromogenic compounds.
Claim 19
Dependent Claim
27 words
The process of claim 16 wherein the alkylation is conducted in the presence of dimethyl sulfate, diethyl sulfate, diazomethane, benzyl chloride or monobromobenzene as the alkylation agent.
Claim 20
Dependent Claim
16 words
The process of claim 17 wherein said alkylation agent is dimethyl sulfate and X represents hydrogen.
Claim 21
Dependent Claim
19 words
The process of claim 15 wherein the xanthyl derivatives are reacted with an acylation agent to form esterified dilactones.
Claim 22
Dependent Claim
17 words
The process of claim 19 wherein said acylation agent is acetic anhydride, butyric anhydride or benzoyl chloride.
Claim 23
Dependent Claim
12 words
The process of claim 20 wherein said acylation agent is benzoyl chloride.
References Cited (Backward Citations)
DE116057C
Cited
GB189503497A
Cited
US656426A
Cited
GB190228638A
Cited
US3244549A
Cited
DD116057A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-05-04 | 1979-11-03 | 1980-05-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-05-04 | 1983-11-03 | 1984-05-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-05-04 | 1987-11-03 | 1988-05-04 | $7700.00 | Window Closed / Lapsed |