Water soluble halogen-containing compounds

Details Water soluble halogen-containing compounds Water soluble halogen-containing compounds

2001-12-11

2003-01-14

Rotman, Alan L. (Department: 1623)

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

Organic compounds

Carboxylic acids and salts thereof

C562S011000, C562S426000, C564S015000, C564S162000, C558S061000, C558S030000

Reexamination Certificate

active

06506934

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to certain water soluble halogen-containing compounds and the preparation of said compounds. These compounds are particularly useful as antifoggants in silver halide photographic materials. These compounds are also useful as water-soluble reagents useful for the bromination of organic chemicals. It is also anticipated that these compounds may be useful as water-soluble oxidants and water-soluble antimicrobial agents.
BACKGROUND OF THE INVENTION
Problems with fogging have plagued the photographic industry from its inception. Fog is a deposit of silver or dye that is not directly related to the image-forming exposure, i.e., when a developer acts upon an emulsion layer, some reduced silver is formed in areas that have not been exposed to light. Fog can be defined as a developed density that is not associated with the action of the image-forming exposure, and is usually expressed as “D-min”, the density obtained in the unexposed portions of the emulsion. Density, as normally measured, includes both that produced by fog and that produced as a function of exposure to light. It is known in the art that the appearance of photographic fog related to intentional or unintentional reduction of silver ion (reduction sensitization) can occur during many stages of preparation of the photographic element including silver halide emulsion preparation, spectral/chemical sensitization of the silver halide emulsion, melting and holding of the liquid silver halide emulsion melts, subsequent coating of silver halide emulsions, and prolonged natural and artificial aging of coated silver halide emulsions. The chemicals used for preventing fog growth as a result of aging or storage are generally known as emulsion stabilizers.
The control of fog, whether occurring during the formation of the light-sensitive silver halide emulsion, during the spectral/chemical sensitization of those emulsions, during the preparation of silver halide compositions prior to coating on an appropriate support, or during the aging of such coated silver halide compositions, has been attempted by a variety of means. Mercury-containing compounds, such as those described in U.S. Pat. Nos. 2,728,663; 2,728,664; and 2,728,665, have been used as additives to control fog. Thiosulfonates and thiosulfonate esters, such as those described in U.S. Pat. Nos. 2,440,206; 2,934,198; 3,047,393; and 4,960,689, have also been employed. Organic dichalcogenides, for example, the disulfide compounds described in U.S. Pat. Nos. 1,962,133; 2,465,149; 2,756,145; 2,935,404; 3,184,313; 3,318,701; 3,409,437; 3,447,925; 4,243,748; 4,463,082; and 4,788,132 have been used not only to prevent formation of fog, but also as desensitizers and as agents in processing baths and as additives in diffusion transfer systems.
However, despite all the efforts in this field there still remains a need for compounds which act as effective antifoggants in photographic elements which are stored under high temperature conditions. There is particularly a need for antifoggants which are water soluble and thus are safer to utilize during manufacture of the photographic elements.
In addition, a problem which has faced synthetic organic chemist is the availability of a reagent for brominating organic chemicals that can be handled safely and is stable when dissolved in water, i.e. a brominating reagent that does not react with water when it is dissolved in water. Molecular bromine is a useful brominating agent but it is not very soluble in water and the toxic liquid is often difficult to handle. Other brominating agents such as the commercially available 1,3-dibromo-5,5-dimethylhydantoin are sometimes sensitive to moisture.
SUMMARY OF THE INVENTION
This invention provides compounds represented by the following Structure I:
 R
1
—SO
2
—C(R
2
)R
3
—(CO)
m
—(L)
n
—SG  I
wherein R
1
is an aliphatic or cyclic group, R
2
and R
3
are independently hydrogen or bromine as long as at least one of them is bromine, L is a divalent linking group, m and n are independently 0 or 1, SG is a solubilizing group with a pKa of 8 or less, with the proviso that when m and n are both 0, SG is not a sulfo (or salt thereof) or a sulfonamido (or salt thereof and when m and n are both 1, either L is not an alkylene group or SG is not a carboxy (or salt thereof).
The compounds of this invention reduce fogging during chemical sensitization of silver halide photographic elements. They further enhance fog retardation of liquid emulsions during high temperature holding. The water soluble antifoggants minimize the need for expensive and time-consuming preparation of solid-particle dispersions, as well as minimize the need for volatile organic solvents. Use of these materials also eliminates the need to use environmentally undesirable heavy metal antifoggant salts such as mercuric salts. It is also believed that these compounds may have utility as antifoggants and stabilizers for thermographic and phototbermographic elements. They may also be useful as brominating agents in the preparation of pharmaceutical compounds and other organic chemicals. Additionally these compounds may be useful as water soluble oxidants and as water soluble antimicrobial agents. These and other advantages will be apparent from the detailed description below.
DETAILED DESCRIPTION OF THE INVENTION
The compounds of this invention are water-soluble or water-dispersible compounds represented by the following Structure I:
R
1
—SO
2
—C(R
2
)R
3
—(CO)
m
—(L)
n
—SG  I
wherein R
1
is a substituted or unsubstituted aliphatic or cyclic group of any size as long as the antifoggant remains soluble or readily dispersible in water. Substituted or unsubstituted aliphatic groups for R
1
include monovalent groups having 1 to 20 carbon, nitrogen, sulfur, and oxygen atoms in the chain including, but not limited to, chains that include one or more substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted alkenylene groups having 2 to 20 carbon atoms, substituted or unsubstituted alkylenearylene groups having 7 to 20 carbon atoms in the chain, and combinations of any of these groups, as well as combinations of these groups that are connected with one or more amino, amido, carbonyl, sulfonyl, carbonamido, sulfonamido, thio, oxy, oxycarbonyl, oxysulfonyl, and other connecting groups that would be readily apparent to one skilled in the art. The various types of useful aliphatic groups would be readily apparent to one skilled in the art. Preferred aliphatic groups for R
1
include substituted or unsubstituted t-butyl groups and trifluoromethyl groups.
R
1
can also be substituted or unsubstituted cyclic groups including substituted or unsubstituted carbocyclic aryl groups having 6 to 14 carbon atoms to fonn the cyclic ring, substituted or unsubstituted cycloalkylene groups (having 5 to 10 carbon atoms to form the cyclic ring) and heterocyclic groups (having 5 to 10 carbon, nitrogen, sulfur, or oxygen atoms to form the cyclic ring), both aromatic and non-aromatic. The various types of cyclic groups would be readily apparent to one skilled in the art.
Preferred cyclic groups for R
1
include substituted or unsubstituted aryl groups having 6 to 10 carbon atoms to form the cyclic ring. Substituted or unsubstituted phenyl groups are most preferred. Methyl groups are preferred substituents on the phenyl group.
In Structure I, R
2
and R
3
are independently hydrogen or bromine as long as one of them is bromine. Preferably, both R
2
and R
3
are bromine.
In addition, L is a substituted or unsubstituted divalent linking group, and more preferably an aliphatic linking group that can have the same definition as R
1
except that L is divalent. Thus, one skilled in the art would be able to determine suitable L groups that would serve the desired purpose while maintaining compound water solubility or dispersibility. Preferably, L is —NH-alkylene wherein “alkylene” is substituted or unsubstituted and has 1 to 10 carbon atoms (more preferably 1 to 3 carbon atom

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