Fluoran compound and coloring recording material using it

Details Fluoran compound and coloring recording material using it Fluoran compound and coloring recording material using it

1989-10-24

1991-05-21

Shen, Cecilia

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549225, 562441, 503217, 503221, 503225, C07D49310, C09B 1128, C07C10178

Patent

active

050177109

DESCRIPTION:

BRIEF SUMMARY
TECHNOLOGICAL FIELDS

This invention relates to new fluoran compounds and coloring recording materials with the said compound as coloring component, and to new intermediates useful for the syntheses of fluoran compounds.


BACKGROUND TECHNOLOGY

Coloring recording materials based on a coloring system consisting of a coloring dye which gives rise to a color by an action of developer though itself is colorless or has almost no color (hereinafter referred to "coloring dye") and a developer coloring the dye are used for, for instance, pressure sensitive copying paper, thermographic recording paper, prepaid cards or POS (point of sales) labels. Their applications are expanding.
A large number of proposals have been offered with regard to fluoran compounds as coloring dyes used for these coloring recording materials, and the fluoran compounds are used in a large amount in the market as well.
Out of the fluoran compounds, those having an anilino group at the 2 position and a methyl group at the 3 position as substituents and a substituted amino group at the 6 position are important as black coloring dyes, are a mainstream of the current market, and have a large number of proposals. That is, compounds having all alkyl groups for all the substituents of the said substituted amino group were proposed in U.S. Pat. No. 3,681,390, etc. Compounds having a cyclohexyl group and lower alkyl group as the substituents of the said substituted amino group are proposed in U.S. Pat. No. 4,410,708, etc. Compounds having a cyclohexyl group and an alkyl group having 5 to 8 carbon atoms are proposed in Japanese open patent No. Sho 60-35053.
However, the coloring performance of these known fluoran coloring dyes is not satisfactory yet. Particularly the improvement of the storability of the dyes is very desired.
The object of this invention is to provide coloring dyes with excellent coloring performance and storability, or coloring dyes with excellent solvility required when used for pressure sensitive copying paper.


DISCLOSURE OF THE INVENTION

This invention is a fluoran compound represented by the general formula (I) ##STR3## (where R is an alkyl group having 9 to 12 carbon atoms) and a coloring recording mataerial containing the said fluoran compound as a coloring dye.
In the fluoran compound represented by the general formula (I), R is a nonyl, decyl, undecyl or dodecyl group.
The fluoran compound represented by the general formula (I) is prepared in a way that a benzoic acid derivative represented by the general formula (II) ##STR4## (where R is as defined above) is reacted with a derivative represented by the following formula ##STR5## of which phenol or phenolic hydroxide group is converted to a lower alkoxy group such as methoxy or ethoxy group, at a molar ratio of about 1:1 in sulfuric acid. The concentration of sulfuric acid used is preferably 80% or more, and the intended product can be obtained by reaction at 0.degree. to 50.degree. C. for several to several 10 hours.
Concrete examples of fluoran compounds thus obtained and represented by the general formula (I) are listed in Table 1.


TABLE 1 ______________________________________ Compound R Melting point (.degree.C.) Color ______________________________________ No. 1 n-C.sub.9 H.sub.19 159-161 a little reddish black No. 2 n-C.sub.10 H.sub.21 135-138 a little reddish black No. 3 n-C.sub.12 H.sub.23 114-117 a little reddish black ______________________________________
The compounds of this invention have superior coloring sensitivity and superior property of less staining on the background, when compared with known analog compounds. Particularly compounds represented by the general formula (I) in which R has 10 or 12 carbon atoms have extremely high coloring sensitivity and extremely high solubility in organic solvents, being preferable compounds.
The fluoran compounds of this invention can of course be used singly to manufacture recording materials coloring black. In addition, two or more of the compounds can be used by mixing or the compound c

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