Diphenylsulfone derivatives and heat sensitive recording materia

Details Diphenylsulfone derivatives and heat sensitive recording materia Diphenylsulfone derivatives and heat sensitive recording materia

1992-03-19

1994-08-23

Ivy, C. Warren

Record receiver having plural interactive leaves or a colorless

Having a colorless color-former, developer therefor, or...

Having nonchromogenic liquid spread-control or...

503225, 549556, 549558, 549559, 549560, 549563, C07D30312, B41M 530

Patent

active

053407881

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELDS

This invention is concerning to novel diphenylsulfone derivatives and heat sensitive recording materials containing the compounds.


BACKGROUND ART

Many kinds of heat sensitive recording materials applying reactions of leuco chromogens with color developing materials have been commonly utilized in recording paper for output recorder of for facsimile and various instruments.
Because, it has been desired as character of the heat sensitive material to be higher sensitive for color evolution, higher whiteness of the background and higher stability of the colored image and toughness of the background concurrently, many kinds of sensitizers and stabilizers have been developed.
Sufficient material for such functions has never been found. Some compounds which were resemble to those of the present invention represented by general formula (I) but involved alkyl group such as isopropyl and glycidyl group at R.sup.1 in the structure were known as adjuvant for heat sensitive recording materials. (Japanese Patent Application (unexamined) Sho 62-164579 (1987)).
The resemble compounds, above mentioned, to those in the invention have been used as storage stabilizer for color image, but their functions have been insufficient. Furthermore, they have toxicological problem such as mutagenicity. Therefore, their disadvantages in the manufacture and marketing have been in very severe circumstances according to the legal control. The purpose of the present invention is to provide a heat sensitive material with outstanding background whiteness, storage stability of the background and of the color image but without the toxicological problems above mentioned.


DISCLOSURE OF INVENTION

This invention is concerning to novel diphenylsulfone derivatives represented in general formula (1), ##STR2## (wherein, R.sup.1 is aralkyl or lower alkenyl which may be substituted with halogen or lower alkyl and R.sup.2 is hydrogen or methyl, but when R.sup.1 is unsubstituted benzyl, R.sup.2 is methyl), and heat sensitive recording materials composing of leuco or faint color chromogens and color developers which develop color, when heated, by the reaction with the chromogens wherein the heat sensitive recording materials contain diphenylsulfone derivatives represented in general formula (I).
The compounds represented by general formula (I) exhibit outstanding excellent characteristics as adjuvant for heat sensitive recording materials and without the toxicological problem such as mutagenicity. In order to clarify the toxicological problem, the mutagenicity of compound No. 1 in the invention was tested comparing with its similar compound 4,4'-diglycidyloxydiphenylsulfone. The results showed as a reference example that the similar compound was mutagenic but no the invented compound was.
Diphenylsulfone derivatives represented by general formula (1) can be manufactured through common reactions of phenols with epichlorohydrins, that is, according to reaction equations as follows: ##STR3##
Other than the above equations, the compounds can be manufactured according to the following oxidative reaction. ##STR4##
Thus synthesized compounds behave polymorphismic crystalline property. The higher melting point type crystal is obtainable from heat melted state or nearly melted state, for example, drying up, is higher melting point type. The crystal can be converted to be lower melting point crystal type by heating in polar solvents such as acetone, chloroform and etc. Additionally, mixtures of lower and higher melting point types of the crystal are possible to be prepared according to these procedures.
For example, for the compound No. 1 in the invention, the lower melting point at 158.degree.-161.degree. C. in example 1, on the other hand the higher melting point at 164.degree.-167.degree. C. in example 2 are obtained.
Typical compounds represented by general formula (I) in the invention are given as described in Table 1.


TABLE 1 ______________________________________ ##STR5## (I) compound Melting No. R.sup.1 R.sup.2 point .degree.C.

REFERENCES:
CA 116: 49023n, 1992.
CA 116: 43199c, 1992.

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