Novel rhodamine dyes

Inactive Publication Date: 2006-12-28
ZINK IMAGING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0040] The novel dyes of the invention are useful in a variety of applications including thermal imaging members and thermal imaging methods. Particularly preferred thermal imaging members and thermal imaging methods, which utilize unsymmetri

Problems solved by technology

On the other hand, unless a fixing step is incorporated, direct thermal systems are still sensitive to heat after thermal printing.
A problem ar

Method used

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  • Novel rhodamine dyes
  • Novel rhodamine dyes
  • Novel rhodamine dyes

Examples

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examples

[0072] The invention will now be described further in detail with respect to specific embodiments by way of examples, it being understood that these are intended to be illustrative only and the invention is not limited to the materials, amounts, procedures and process parameters, etc. recited therein. All parts and percentages recited are by weight unless otherwise specified.

example i

Synthesis of N-acetyl-N-octylaniline

[0073] 1-octyl bromide (39 mL, 224 mmol, 1.12 eq) was added dropwise to a mixture of acetanilide (27 g, 200 mmol, 1 eq.) in dimethylsulfoxide (130 mL), containing potassium hydroxide pellets (18.87 g, 300 mmol, 1.5 eq.), at room temperature. After all the 1-octyl bromide was added the reaction mixture was heated to 50-55° C. for 1.5 hours. The reaction mixture was cooled and poured into water (1 L), stirred for 45 minutes and extracted with hexanes (3×400 mL). The hexane extracts were combined, dried over sodium sulfate and evaporated to give 48.4 g (196 mmol, 98%) of colorless oil. The product was identified by NMR spectroscopy and mass spectrometry and was used without further purification.

Synthesis of N-octylaniline

[0074] To N-acetyl-N-octylaniline (48.4 g, 196 mmol) was added 4N hydrochloric acid (100 mL) and the mixture heated to 100-110° C. and stirred at this temperature for 4 days. The reaction mixture was cooled to ambient temperature,...

example ii

Synthesis of Dye I

[0082] A mixture of 3′-chloro-6′-tetrahydroquinolinofluoran (100 mg, 0.2 mmol), decylamine (100 mg, 0.6 mmoles), and zinc chloride (100 mg, 0.7 mmol) in sulfolane (3 mL) was held at 150° C. for 3 hours. The reaction mixture was quenched into 10 ml of water. The solid was filtered off, washed with water and dried. The product was purified by silica gel chromatography using 2% methanol in methylene chloride to yield Dye I, 3′N-decylamino-6-tetrahydroquinoline fluoran as an off-white solid (42 mg, 0.07 mmol, 35%). The product was identified by NMR spectroscopy and mass spectrometry, m.p. 124° C.

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Abstract

There are described novel rhodamine color-forming compounds. The rhodamine color-forming compounds exhibit a first color when in a crystalline form and a second color, different from the first color, when in an amorphous form.

Description

REFERENCE TO RELATED APPLICATIONS [0001] This application claims the benefit of priority of provisional patent applications Ser. Nos. 60 / 680,088 and 60 / 680,212, both filed May 12, 2005, the contents of which are incorporated herein by reference in their entireties. [0002] This application is related to the following commonly assigned, United States patent applications and patents, the contents of which are incorporated herein by reference in their entireties: [0003] U.S. Pat. No. 6,801,233 B2; [0004] U.S. Pat. No. 6,906,735 B2; [0005] U.S. Pat. No. 6,951,952 B2; [0006] U.S. Pat. No. 7,008,759 B2; [0007] U.S. patent application Ser. No. 10 / 806,749, filed Mar. 23, 2004, which is a division of U.S. Pat. No. 6,801,233 B2; [0008] United States Patent Application Publication No. US2004 / 0176248 A1; (Attorney docket No. A-8544AFP); [0009] United States Patent Application Publication No. US2004 / 0204317 A1; (Attorney Docket No. A-8586AFP); [0010] United States Patent Application Publication N...

Claims

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Application Information

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IPC IPC(8): C07D491/14C07D311/88
CPCB41M5/3275B41M5/3335B41M5/3375C09B67/0025B41M5/385C07D493/10C09B11/24B41M5/38235C07D493/20
Inventor FILOSA, MICHAEL P.MARSHALL, JOHN L.ALLEN, RICHARD M.
Owner ZINK IMAGING
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