3-phenyl-7-[4-(tetrahydrofurfuryloxy)phenyl]-1,5-d...

Details 3-phenyl-7-[4-(tetrahydrofurfuryloxy)phenyl]-1,5-d... 3-phenyl-7-[4-(tetrahydrofurfuryloxy)phenyl]-1,5-d...

1994-04-19

2001-04-17

Krass, Frederick (Department: 1614)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S412000, C008S636000, C008S675000, C008S677000, C008S678000, C008S115510, C252S008910, C252S008050, C252S008910, C428S364000, C428S365000

Reexamination Certificate

active

06218552

ABSTRACT:

BACKGROUND OF THE INVENTION
The present invention relates to a compound, 3-phenyl-7-[4-(tetrahydrofurfuryloxy)-phenyl]-1,5-dioxa-s-indacene-2,6-dione, having a specific structure of crystals. More particularly, it relates to 3-phenyl-7-[4-(tetrahydrofurfuryloxy)phenyl]-1,5-dioxa-s-indacene-2,6-dione which has a structure of crystals useful for dyeing or printing hydrophobic fiber materials particularly in a deep tint of colors.
Description of the Prior Art
Japanese Patent 3-72571A (U.S. Pat. No. 5,424,455) and 4-164967A (U.S. Pat. No. 5,286,881) teach various benzodifuranone compounds. It has been known that these compounds are able to dye hydrophobic fiber materials, for example, polyester fiber materials, in red color. However, dyeabilities of these compounds are not yet sufficient to meet higher requisites sought in recent years, and a solution to this problem has been highly desired.
Summary of the Invention
The present inventors have extensively studied on dyeabilities of these benzodifuranone compounds, and accomplished the present invention based on the findings that a specific compound among them has polymorphism of crystals and a specific crystal modification of the compound endows an excellent dyeability, particularly, to give a dyed product in a deep tint of colors.
Accordingly, the present invention is to provide for 3-phenyl-7-[4-(tetrahydro-furfuryloxy)phenyl]-1,5-dioxa-s-indacene-2,6-dione having a structure of crystals which exhibits the strongest peak at an angle of diffraction, 2&thgr;, of 4.7°, among peaks appearing within the range of not smaller than 3° of 2&thgr; in an X-ray diffraction using a Cu-K&agr; -ray. Hereinafter, the crystalline structure of 3-phenyl-7-[4-(tetra-hydrofurfuryloxy)-phenyl]-1,5-dioxa-s-indacene-2,6-dione which exhibits the characteristic peak as mentioned above at an angle of diffraction, 2&thgr;, in an X-ray diffraction is referred to as “alpha-crystal modification”.
The alpha-crystal modification in the present invention exhibits a characteristic sharp peak, i.e. strongest peak, at an angle of diffraction, 2&thgr; of 4.7°, so far as 2&thgr; is within the range of not smaller than 3°, when being subjected to an X-ray diffraction using Cu-K&agr; -rays. The whole X-ray diffraction pattern, particularly intensity of each peak, varies depending upon manufacturing conditions, but a typical diffraction pattern from the alpha-crystal modification when being subjected to an X-ray diffraction using a Cu-K&agr; -ray is as shown in the FIGURE attached. Peaks of medium strength at 17.3° and 19.2°, and peaks of weak strength at 7.1° and 9.4°, of 2&thgr;, are also characteristics of the alpha-crystal modification.
The peaks usually appearing in an X-ray diffraction pattern using a Cu-K&agr; -ray from the alpha-crystal modification in the present invention are listed as follows:
Strong peak: 4.7°
Medium peaks: 17.3°, 19.2°, 26.0°, 27.0°, 27.4°
Weak peaks: 7.1°, 9.4°, 14.4°, 23.0°


REFERENCES:
patent: 5286881 (1994-02-01), Sekihachi et al.
patent: 5424455 (1995-06-01), Yamamoto et al.
patent: 146269 (1985-06-01), None
patent: 397170 (1990-11-01), None
patent: 436940 (1991-07-01), None
patent: 0494537 (1992-07-01), None
patent: 4164967 (1990-02-01), None
patent: 3-72571 (1990-02-01), None
patent: 372571 (1991-03-01), None
patent: 4164967 (1992-06-01), None
Chemische Berichte, vol. 30, 124 (1897), with translation.
Prager et al. System No. 1106/H410-411, vol. 10, Beilsteins Handbuch der Organischen Chemie and Enlarged edition thereof, 1927.
Encylopedia of Chemical Technology, vol. 24, pp. 678-708 (John Wiley & Sons, 3rd Edition, 1984).

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