Record receiver having plural interactive leaves or a colorless – Having a colorless color-former – developer therefor – or... – Identified color-former
Reexamination Certificate
2001-02-26
2003-10-21
Hess, Bruce H. (Department: 1774)
Record receiver having plural interactive leaves or a colorless
Having a colorless color-former, developer therefor, or...
Identified color-former
C106S031220, C546S015000, C549S224000, C549S225000, C549S226000
Reexamination Certificate
active
06635602
ABSTRACT:
TECHNICAL FIELD
The present invention relates to mixtures of fluoran compounds which are useful as colour forming compounds in recording materials. More particularly, the invention relates to a process for the preparation of said mixtures of fluoran compounds and to the use of said mixtures of fluoran compounds as colour formers in recording materials such as heat sensitive and pressure sensitive recording materials.
DESCRIPTION OF THE PRIOR ART
Pressure sensitive recording, heat sensitive recording and electroheat sensitive recording have conventionally been used as systems for recording transferred information through the mediation of external energy, such as pressure, heat or electricity, by utilising a colour reaction between a colourless or pale coloured electron donative compound (colour forming compound) and an organic or inorganic electron acceptor (developer).
In such recording systems, mixtures of more than one colour former have been used as the colour forming compound. For example, U.S. Pat. No. 4,226,912 discloses a system wherein the chromogenic material is a physical mixture of two black fluoran colour formers in a heat sensitive recording system. At present, such mixtures of fluorans are prepared by physical mixing of the component fluoran colour formers. Where a mixture of more than one colour former is to be used then, an additional mixing step is necessary in the preparation of the final recording system. It is advantageous to mix thoroughly in order to generate a homogenous system. To achieve good mixing the intensity of mixing and the time of mixing can be altered. However, unless separate analysis of the mixture is carried out the relative composition of the dispersed system is unknown. In addition, where two or more colour formers are used the relative purity/impurity of each component may have an impact on the final characteristics of the recording material. As such, the formulators challenge is to develop a multi-colour former system in which the individual components are present at optimal purity levels in order to deliver desirable recording properties and yet which can be manufactured both simply and efficiently.
It has now been found that mixtures of specified fluoran colour forming compounds can be synthesised directly by the reaction of at least two derivatives of amino phenols, phthalic anhydrides, keto acids and/or diphenylamines with a phenol derivative. The advantages of the present process are that a separate mixing step in the preparation of the final recording system is obviated with the relevant savings in time and energy in the process and the relative impact of mixed impurities or impurity levels from differing colour former components is reduced.
OBJECT OF THE INVENTION
An object of the present invention is to provide an efficient process for the manufacture of mixtures of fluoran compounds that does not require separate manufacture of the individual component fluoran compounds, subsequent mixing and further treatment of the mixture. Thus the present invention provides a novel process for the manufacture of mixtures of fluoran compounds from appropriate mixtures of starting materials in a single process.
DETAILED DESCRIPTION OF THE INVENTION
The mixtures of fluorans prepared by the present invention may be amorphous mixtures, mixed crystals, monophase solid solutions, multiphase solid solutions, aggregates of different compounds each in pure crystal modification and mixtures thereof.
In the literature, the definitions by the various authors, such as, G. H. Van't Hoff, A. I. Kitaigorodsky and A. Whitacker for solid solutions and mixed crystals are often contradictory, (cf, e.g. ‘Analytical Chemistry of Synthetic Dyes’, Chapter 10/page 269. Editor K. Venkataraman, J. Wiley, New York, 1977). The term ‘monophase solid solution’ or ‘multiphase solid solution’ or mixed crystal’, as defined herein, therefore, should be taken from the following definitions, which have been adapted to the current improved state of knowledge of such systems:
A monophase (or single-phase or guest-host) solid solution possesses a crystal lattice which is identical with the crystal lattice of one of its components. One component is embedded as the ‘guest’ in the crystal lattice of the other component, which acts as the ‘host’. The X-ray diffraction pattern of such a monophase solid solution is substantially identical to that of one of the components, called the ‘host’. Within certain limits, different proportions of the components produce almost identical results.
A multiphase solid solution possesses no precise, uniform crystal lattice. It differs from a physical mixture of its components in that the crystal lattice of at least one of its components is partially or completely altered. In comparison to a physical mixture of the components, which gives an X-ray diffraction diagram that is additive of the diagrams seen for the individual components. The signals in the X-ray diffraction diagram of a multiphase solid solution are broadened, shifted or altered in intensity. In general, different proportions of the components produce different results.
A mixed crystal (or solid compound type) solid solution possesses a precise composition and a uniform crystal lattice, which is different from the crystal lattices of all its components. If different proportions of the components lead, within certain limits, to the same result, then a solid solution is present in which the mixed crystal acts as a host.
As hereinbefore detailed, the novel mixtures of fluorans comprise a plurality of colour forming compounds. Suitable mixtures of fluoran colour forming materials which may be prepared according to the present invention may include at least one fluoran compound such as 3-dibutylamino-7-dibenzylaminofluoran, 3-diethylamino-6-methylfluoran, 3-dimethylamino-6-methyl-7-anilinofluoran, 3-diethylamino-6-methyl-7-anilinofluoran, 3-diethylamino-6-methyl-7-(2,4-dimethylanilino)fluoran, 3-diethylamino-methyl-7-chlorofluoran, 3-diethylamino-6-methyl-7-(3-trifluoromethylanilino)fluoran, 3-diethylamino-6-methyl-7-(2-chloroanilino)fluoran, 3-diethylamino-6-methyl-7-(4-chloroanilino)fluoran, 3-diethylamino-6-methyl-7-(2-fluoroanilino)fluoran, 3-diethylamino-6-methyl-7-(4-n-octylanilino)fluoran, 3-diethylamino-7-(4-n-octylanilino)fluoran, 3-diethylamino-7-(n-octylamino)fluoran, 3-diethylamino-6-methyl-7-(dibenzylamino)fluoran, 3-diethylamino-7-(dibenzylamino)fluoran, 3-diethylamino-6-chloro-7-methylfluoran, 3-diethylamino-7-t-butylfluoran, 3-diethylamino-7-carboxyethylfluoran, 3-diethylamino-6-chloro-7-anilinofluoran, 3-diethylamino-6-methyl-7-(3-methylanilino)fluoran, 3-diethylamino4—methyl-7-(4-methylanilino)fluoran, 3-diethylamino-6-ethoxyethyl-7-anilinofluoran, 3-diethylamino-7-methylfluoran, 3-diethylamino-7-chlorofluoran, 3-diethylamino-7-(3-trifluoromethylanilino)fluoran, 3-diethylamino-7-(2-chloroanilino)fluoran, 3-diethylamino-7-(2-fluoroanilino)fluoran, 3-diethylamino-benzo[a]fluoran, 3-diethylamino-benzo[c]fluoran, 3-dibutylamino-6-methyl fluoran, 3-dibutylamino-methyl-7-anilinofluoran, 3-dibutylamino-6-methyl-7-(2,4-dimethylanilino)fluoran, 3-dibutylamino-6-methyl-7-(2-chloroanilino)fluoran, 3-dibutylamino-6-methyl-7-(4-chloroanilino)fluoran, 3-dibutylamino-6-methyl-7-(2-fluoroanilino)fluoran, 3-dibutylamino-6-methyl-7-(3-trifluoromethylanilino)fluoran, 3-dibutylamino-6-ethoxyethyl-7-anilinofluoran, 3-dibutylamino-6-chloro-anilinofluoran, 3-dibutylamino-6-methyl-7-(4-methylanilino)fluoran, 3-dibutylamino-7-(2-chloroanilino)fluoran, 3-dibutylamino-7-(2-fluoroanilino)fluoran, 3-dipentylamino-6-methyl-7-anilinofluoran, 3-dipentylamino-6-methyl-7-(4-chloroanilino)fluoran, 3-dipentylamino-7-(3-trifluoromethylanilino)fluoran, 3-dipentylamino-6-chloro-7-anilinofluoran, 3-dipentylamino-7-(4-chloroanilino)fluoran, 3-pyrrolidino-6-methyl-7-anilinofluoran, 3-piperidino-6-methyl-7-anilinofluoran, 3-(N-methyl-N-propylamino)-methyl-7-anilinofluoran, 3-(N-methyl-N-cyclohexylamino)-6-methyl-7-anilinofluoran, 3-(N-ethyl-N-cyclohexylamino)-4-methyl-7-anilinofluoran, 3-(N-e
Heneghan Michael
Taylor James Philip
Ciba Specialty Chemicals Corporation
Hess Bruce H.
Mansfield Kevin T.
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