Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
2002-08-02
2004-06-08
Richter, Johann R. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C560S171000
Reexamination Certificate
active
06747169
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a novel fluorine compound and surfactant that can impart surface functions such as water and oil repelling properties, antifouling property and antistatic property as well as an aqueous coating composition and silver halide photographic light-sensitive material utilizing them.
RELATED ART
Compounds having a fluorinated alkyl chain are conventionally known as surfactants. Such surfactants enables modifications of various surface properties by the unique properties of the fluorinated alkyl chain (e.g., water and oil repelling properties, lubricity, antistatic property etc.), and they are used for surface treatment of base materials of a wide range such as fibers, cloth, carpets and resins. Further, if a surfactant having a fluorinated alkyl chain (henceforth referred to as a “fluorine-containing surfactant”) is added to a solution of any of various substrates in an aqueous medium, not only a uniform coating film can be formed without repellency upon coating, but also a surfactant-adsorbed layer can be formed on a substrate surface and thus the unique properties provided by the fluorinated alkyl chain can be imparted to the surface of coating.
Also in photographic light-sensitive materials, various surfactants are used and play important roles. Photographic light-sensitive materials are usually produced by separately coating a plurality of coating solutions including an aqueous solution of a hydrophilic colloid binder (e.g., gelatin) on a support to form multiple layers. Multiple hydrophilic colloid layers are often simultaneously coated as stacked layers. These layers include antistatic layer, undercoat layer, antihalation layer, silver halide emulsion layer, intermediate layer, filter layer, protective layer and so forth, and various materials for exerting functions of the layers are added to the layers. Further, polymer latex may also be added to the hydrophilic colloid layer in some cases in order to improve physical properties of film. Furthermore, in order to add functional compounds hardly soluble in water such as color couplers, ultraviolet absorbers, fluorescent brightening agents and lubricants to the hydrophilic colloid layer, these materials are sometimes emulsion-dispersed in a hydrophilic colloid solution as they are or as a solution in a high boiling point organic solvent such as phosphoric acid ester compounds and phthalic acid ester compounds for the preparation of a coating solution. As described above, photographic light-sensitive materials are generally constituted by various hydrophilic colloid layers, and in the production of them, it is required to uniformly coat coating solutions containing various materials at a high speed without defects such as repelling and uneven coating. In order to meet such requirements, a surfactant is often added to a coating solution as a coating aid.
Meanwhile, photographic light-sensitive materials are brought into contact with various materials during production, light exposure and development thereof. For example, if a light-sensitive material is in a rolled shape in process steps, a back layer formed on the back surface of the support may contact with the surface layer. Further, when it is transported during process steps, it may contact with stainless steel rollers, rubber rollers etc. When they are brought into contact with these materials, surfaces (gelatin layer) of light-sensitive materials are likely to be positively charged and they may undesirably cause discharge as the case may be. Therefore, there may remain undesirable traces of light exposure (called static marks) on the light-sensitive materials. In order to reduce this electrification property of gelatin, a compound containing a fluorine atom is effective, and a fluorine-containing surfactant is often added.
As described above, surfactants, especially fluorine-containing surfactants, are used as materials having both of the function as coating aids for providing uniformity of coated films and the function for imparting antistatic property to photographic light-sensitive materials. Specific examples thereof are disclosed in, for example, Japanese Patent Laid-open Publication (Kokai, henceforth referred to as JP-A) No. 49-46733, JP-A-51-32322, JP-A-57-64228, JP-A-64-536, JP-A-2-141739, JP-A-3-95550, JP-A-4-248543 and so forth. However, these materials do not necessarily have performance satisfying the demands for higher sensitivity and coating at higher speed required for recent photographic light-sensitive materials, and it is desired to further improve fluorine-containing surfactants. Although it is generally considered that a shorter perfluoroalkyl chain would be advantageous in degradability (degradability of compound after use), it markedly degrades orientation of the fluorinated alkyl chain on the surface of coated film. Therefore, it is strongly desired to develop a fluorine-containing surfactant that has a shorter fluoroalkyl chain and can also provide both of surface orientation (it relates to antistatic property) and uniformity of coated film.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a novel fluorine compound that has a short perfluoroalkyl group, but shows superior surface orientation and enables formation of uniform coated films when used in formation of coated films, and a surfactant containing it. Another object of the present invention is to provide an aqueous coating composition that enables formation of uniform coated films having antistatic property. A further object of the present invention is to provide a silver halide photographic light-sensitive material that can be stably produced and is imparted with antistatic property.
In order to achieve the aforementioned objects, the silver halide photographic light-sensitive material of the present invention is a silver halide photographic light-sensitive material having one or more layers including a light-sensitive silver halide emulsion layer on a support, wherein any of the layers contains a compound represented by the following formula (1).
In the formula, R
1
and R
2
each represent a substituted or unsubstituted alkyl group provided that at least one of R
1
and R
2
represents an alkyl group substituted with one or more fluorine atoms. R
3
, R
4
and R
5
each independently represent a hydrogen atom or a substituent, X
1
, X
2
and Z each independently represent a divalent bridging group or a single bond, and M
+
represents a cationic substituent. Y
−
represents a counter anion, but Y
−
may not be present when the intramolecular charge excluding Y
−
is 0. m is 0 or 1.
As preferred embodiments of the present invention, there are provided the aforementioned silver halide photographic light-sensitive material, which has a light-insensitive hydrophilic colloid layer as an outermost layer and contains a compound represented by the aforementioned formula (1) in the outermost layer; and the aforementioned silver halide photographic light-sensitive material, which contains a compound represented by the aforementioned formula (1) and an anionic or nonionic surfactant in the outermost layer. As a preferred embodiment of the present invention, there is also provided the aforementioned silver halide photographic light-sensitive material, wherein the compound represented by the aforementioned formula (1) is a compound represented by the following general following formula (1-a), and as a more preferred embodiment of the present invention, there is provided the aforementioned silver halide photographic light-sensitive material, wherein the compound represented by the aforementioned formula (1) is a compound represented by the following general following formula (1-c).
In the formula, R
11
and R
21
each represent a substituted or unsubstituted alkyl group provided that at least one of R
11
and R
21
represents an alkyl group substituted with one or more fluorine atoms and the total carbon atom number of R
11
and R
21
is 19 or less. R
13
, R
14
and R
15
each independently represent a subst
Hamamoto Nobuo
Ikeda Akira
Ishizuka Takahiro
Yanagi Terukazu
Fuji Photo Film Co. , Ltd.
Richter Johann R.
Zucker Paul A.
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