Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Utility Patent
2000-01-24
2001-01-02
Barts, Samuel (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C564S430000, C564S441000, C564S223000, C564S050000, C564S079000, C564S440000, C549S491000, C549S475000, C549S409000, C549S057000, C558S418000, C562S058000, C562S452000, C560S029000, C560S032000, C546S136000, C546S300000, C548S530000, C548S511000, C544S059000, C430S467000
Utility Patent
active
06169206
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to 4-(N,N-dialkylamino)aniline compounds. In particular, the present invention relates to new 4-(N,N-dialkylamino)aniline compounds useful as developing agents for silver halide color photography or as dyes or intermediates therefor.
4-(N,N-Dialkylamino)aniline compounds are useful as developing agents for silver halide color photography, and they are described in, for example, Japanese Patent Unexamined Published Application (hereinafter referred to as “J. P. KOKAI”) Nos. Hei 5-257248, 6-161061 and 7-36162. 4-Aminoaniline, i.e. p-phenylenediamine, is useful as an intermediate for a dye for keratin fibers such as human hair.
SUMMARY OF THE INVENTION
The object of the present invention is to provide new 4-((N,N-dialkylamino)aniline compounds useful as developing agents having an excellent graininess for silver halide color photography, as dyes and intermediates therefor, particularly intermediates for dyes for keratin fibers such as human hair, as medicines and intermediates therefor, and agricultural chemicals and intermediates therefor.
The above-described object can be attained by the following compounds, composition and method
(1) aniline compounds of the following general formula (I):
wherein R
1
represents an alkyl group, an aryl group or a heterocyclic group, R
2
to R
5
each represents a hydrogen atom or a substituent, and R
2
and R
3
, R
1
and R
2
, or R
4
and R
5
may form a ring together,
(2) a processing composition for color photography, which contains at least one of the compounds set forth in above item (1), and
(3) a color image-forming method wherein an image-exposed sensitive silver halide color photographic material is developed in the presence of at least one of the compounds set forth in above item (1).
4-(N,N-dialkylamino)aniline compounds having a saccharide group, i.e. 2,3,4,5,6-pentahydroxyhexyl group, as a 4-N substituent in the present invention are useful not only as color developing agents for silver halide color photography but also as intermediates for dyes for keratin fibers such as human hair, or as medicines and agricultural chemicals and intermediates for them.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The detailed description will be made on the general formula (I). R
1
represents an alkyl group, an aryl group or a heterocyclic group. Such a group may be substituted with a substituent such as an alkyl group, alkenyl group, alkynyl group, aryl group, hydroxyl group, nitro group, cyano group, or halogen atom or with another substituent comprising oxygen atom, nitrogen atom, sulfur atom and/or carbon atom. When R
1
is an alkyl group, it is preferred that, among the carbon atoms in R
1
, the carbon atom directly bonded to the nitrogen atom in the general formula (I) is not bonded to an element other than hydrogen or carbon element. When R
1
is a heterocyclic group, it is preferred that a carbon atom constituting the heterocycle is connected with the nitrogen atom in the general formula (I). The alkyl groups may be linear, branched or cyclic alkyl groups having 1 to 25 carbon atoms, preferably 1 to 15 carbon atoms, such as methyl, ethyl, propyl, isopropyl, t-butyl, 2-hydroxyethyl, 3-hydroxypropyl, benzyl, 2-methanesulfonamidoethyl, 3-methanesulfonamidopropyl, 2-methanesulfonylethyl, 2-methoxylethyl, cyclopentyl, 2-acetamidoethyl, hydroxymethyl, 2-carboxyethyl, 2-carbamoylethyl, 3-carbamoylpropyl, 2,3-dihydroxypropyl, 3,4-dihydroxybutyl, 2,3,4-trihydroxybutyl, 2,3,4,5-tetrahydroxypentyl, methanesulfonamidomethyl, n-hexyl, n-octyl, n-decyl, n-octadecyl, 2-ethylhexyl, 2-hydroxypropyl, 4-hydroxybutyl, 2-carbamoylaminoethyl, 3-carbamoylaminopropyl, 4-carbamoylaminobutyl, 4-carbamoylbutyl, 2-carbamoyl-1-methylethyl, carbamoylaminomethyl, 4-nitrobutyl, 2-(2-hydroxyethoxy)ethyl, 2-[2-(2-hydroxyethoxy)ethoxy]ethyl, 2-(2-[2-(2-hydroxyethoxy)ethoxy]ethoxy)ethyl, 2-[2-(2-[2-(2-hydroxyethoxy) ethoxy]ethoxy)ethoxy]ethyl, 2-(2-[2-(2-[2-(2-hydroxyethoxy) ethoxy]ethoxy)ethoxy]ethoxy)ethyl, 2-[2-(2-(2-(2-[2-(2-hydroxyethoxy) ethoxy]ethoxy)ethoxy]ethoxy)ethoxy)ethyl, 2-(2-[2-(2-[2-(2-[2-(2-hydroxyethoxy)ethoxy]ethoxy)ethoxy]ethoxy)ethoxy]ethoxy)ethyl, 2-(2-methoxyethoxy)ethyl, 2-[2-(2-methoxyethoxy)ethoxy]ethyl, 2-(2-[2-(2-methoxyethoxy)ethoxy]ethoxy)ethyl, 2-[2-(2-[2-(2-methoxyethoxy) ethoxy]ethoxy)ethoxy]ethyl, 2-(2-ethoxyethoxy)ethyl and 2-[2-(2-butoxyethoxy)ethoxy]ethyl groups. In addition, the alkyl groups may be such as cyclohexyl, n-pentyl, n-heptyl, 2-[2-(2-phenyloxyethoxy) ethoxy]ethyl, n-butyl, n-nonyl, 2-(N,N-dimethylamino)ethyl and 2-mercaptoethyl groups.
The aryl groups may be those having 6 to 24 carbon atoms such as phenyl, naphthyl and p-methoxyphenyl groups. In addition, the aryl groups may be such as hydroxyphenyl, p-aminophenyl and N,N-diaminophenyl groups. The heterocyclic groups may be five-membered or six-membered, saturated or unsaturated heterocyclic groups containing 1 to 5 carbon atoms and at least one of oxygen, nitrogen and sulfur atoms. The number of the hetero atom constituting the ring may be one or more, and when the ring contains two or more elements of the hetero atoms, the kind of them may be the same or different. The heterocyclic groups include 2-furyl, 2-thienyl, 2-pyrimidinyl, 2-benzotriazolyl, imidazolyl and pyrazolyl groups.
R
1
is preferably an alkyl group or an aryl group, particularly the alkyl group.
Preferred examples of R
1
include methyl, ethyl, propyl, isopropyl, 2-hydroxyethyl, 3-hydroxypropyl, benzyl, 2-me thanesulfonamidoethyl, 2,3-dihydroxypropyl, 3,4-dihydroxybutyl, 2,3,4-trihydroxybutyl, 2,3,4,5-tetrahydroxypentyl, n-hexyl, n-octyl, n-decyl, n-octadecyl, 2-ethylhexyl, 2-hydroxypropyl, 4-hydroxybutyl, 2-(2-hydroxyethoxy)ethyl, 2-[2-(2-hydroxyethoxy)ethoxy]ethyl, 2-(2-[2-(2-hydroxyethoxy)ethoxy]ethoxy)ethyl, 2-[2-(2-[2-(2-hydroxyethoxy) ethoxy]ethoxy)ethoxy]ethyl, 2-(2-[2-(2-[2-(2-hydroxyethoxy) ethoxy]ethoxy)ethoxy]ethoxy)ethyl, 2-(2-methoxyethoxy)ethyl, 2-[2-(2-methoxyethoxy)ethoxy]ethyl, 2-[2-(2-butoxyethoxy)ethoxy]ethyl, phenyl and p-methoxyphenyl. Particularly preferred examples of R
1
include methyl, ethyl, propyl, isopropyl, 2-hydroxyethyl, 2,3-dihydroxypropyl, 3,4-dihydroxybutyl, n-hexyl, n-octyl, n-decyl, n-octadecyl, 2-ethylhexyl, 2-(2-hydroxyethoxy)ethyl, 2-[2-(2-hydroxyethoxy)ethoxy]ethyl, 2-(2-[2-(2-hydroxyethoxy)ethoxy]ethoxy)ethyl, 2-(2-methoxyethoxy)ethyl, 2-[2-(2-methoxyethoxy)ethoxy]ethyl, 2-[2-(2-butoxyethoxy)ethoxy]ethyl and phenyl.
R
2
to R
5
each represents a hydrogen atom or a substituent. Examples of the substituents include halogen atoms and groups such as alkyl, aryl, heterocyclic, cyano, nitro, hydroxyl, carboxyl, sulfo, alkoxyl, aryloxy, acylamino, amino, alkylamino, anilino, ureido, sulfamoylamino, alkylthio, arylthio, alkoxycarbonylamino, sulfonamido, carbamoyl, sulfamoyl, sulfonyl, alkoxycarbonyl, heterocyclic oxy, azo, acyloxy, carbamoyloxy, silyl, silyloxy, aryloxycarbonylamino, imido, heterocyclic thio, sulfinyl, phosphonyl, aryloxycarbonyl and acyl groups. Examples of the substituents also include mercapto and sulfino groups. They may be substituted with an alkyl group, alkenyl group, alkynyl group, aryl group, hydroxyl group, nitro group, cyano group, halogen atom or another substituent comprising oxygen atom, nitrogen atom, sulfur atom and/or carbon atom.
As for the detailed examples of substituents R
2
to R
5
, the halogen atoms may be, for example, fluorine atom or chlorine atom. In addition, the halogen atoms may be bromine atom. The alkyl groups, aryl groups and heterocyclic groups may be those described above with reference to R
1
.
The alkoxyl groups may be those having 1 to 16 carbon atoms, preferably 1 to 6 carbon atoms, such as methoxyl, ethoxyl, 2-methoxyethoxyl and 2-methanesulfonylethoxyl groups. The aryloxy g
Hirano Shigeo
Kawamoto Hiroshi
Kimura Keizo
Barts Samuel
Burns Doane , Swecker, Mathis LLP
Fuji Photo Film Co. , Ltd.
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