Radiation imagery chemistry: process – composition – or product th – Radiation sensitive product – Identified backing or protective layer containing
Reexamination Certificate
2003-06-23
2004-08-24
Schilling, Richard L. (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Radiation sensitive product
Identified backing or protective layer containing
C430S535000, C430S536000, C430S537000, C430S636000, C548S307100
Reexamination Certificate
active
06780576
ABSTRACT:
FIELD OF THE INVENTION
The present invention concerns 2-thioalkyl-benzimidazole-5-sulphonic acid and 2-thioalkyl-benzimidazole-6-sulphonic acid compounds and their use as surfactants.
BACKGROUND OF THE INVENTION
U.S. Pat. No. 2,053,822 discloses a process for the manufacture of sulphonic acids, consisting in treating with sulphonating agents imidazole derivatives having the atom grouping
in which R represents a carbocyclic aromatic radical containing at the most 10 carbon atoms, R
1
represents an alkyl radical containing at least 7 carbon atoms and R
2
is a member selected from the group consisting of hydrogen and alkyl. None of the alkylating agents cited contains an aromatic group i.e. benzyl chloride is apparently not included. The aromatic nucleus R may comprise substituents, for example, sulpho groups. The 2-substituent may also be a methoxy-, ethoxy-, mercapto- or thioalkyl-group. U.S. Pat. No. 2,053,822 further discloses that new imidazoles are characterized by the atom grouping
wherein the radical R represents a sulphonated aromatic radical, wherein further the nature of the &mgr;-substituent follows from the above enumerations, and wherein at least one of the two nitrogen atoms is linked with a radical R
1
. The examples disclose the reaction of dodecyl chloride, 2-chloroacetic acid dodecyl ester with &mgr;-heptadecyl-benzimidazole followed by sulphonation.
Thermography is an image-forming process including a heating step and hence includes photothermography in which the image-forming process includes image-wise exposure and direct thermal processes in which the image-forming process includes an image-wise heating step. In direct thermal printing a visible image pattern is produced by image-wise heating of a recording material.
U.S. Pat. No. 3,704,130 discloses a method of preparing a photographic fine-grain silver halide emulsion, which comprises the step of precipitating the silver halide in an aqueous hydrophilic colloid medium in the presence of a compound corresponding to the following general formula: Z-A-X, wherein: each of Z and X (the same or different) stands for a heterocycle or a heterocycle with fused-on ring, said heterocycle comprising the moiety ═N—, and A stands for a chemical bond, alkylene, alkylene interrupted by oxygen or —N(R)— wherein R=hydrogen or alkyl comprising at most 4 C-atoms, arylene, alkenylene, —S-alkylene-S— or —S-alkylene, the alkylene groups of which can be interrupted by oxygen or —N(R)— wherein R has the same significance as above; said compound being present in an amount sufficient to restrain growth of silver halide grains. U.S. Pat. No. 3,704,130 discloses the following 2-alkylthio-benzimidazole-6-sulphonic acid compounds as Compound 7:
U.S. Pat. No. 4,639,408 discloses a process for forming an image comprising a heating step wherein a silver halide light-sensitive photographic material is heated in the presence of a compound represented by formula (I)
wherein X represents an atomic group completing a carbocyclic aromatic ring or a heterocyclic aromatic ring; R
1
is selected from selected from groups represented by formulae (A), (B), and (C):
—SO
2
—R
11
(A)
—C(═O)—R
11
(B)
—P(═O)R
11
R
12
(C)
in which R
11
and R
12
each represents a substituted or unsubstituted alkyl group, a cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, an alkoxy or aryloxy group, an alkylthio or arylthio group, or a substituted or unsubstituted amino group, or R
11
and R
12
together form a 5-membered or 6-membered ring; R
2
represents a group selected from the groups represented by R
11
; R
1
and R
2
together form a 5-membered or 6-membered ring; Q represents a hydrogen atom, an alkyl group, or an aryl group; TIME represents a timing group; PUG represents a photographically useful group; and n represents 0 or an integer, wherein the photographic material contains a base or a base precursor. U.S. Pat. No. 4,639,408 discloses the following 2-alkylthio-benzimidazole-6-sulphonic acid compounds as Compound (8):
Surfactants with excellent latex-stabilizing properties, which enhance the adhesion of hydrophilic layers to hydrophobic supports, such as polyethylene terephthalate and hydrophobic thermosensitive elements of substantially light-insensitive thermographic recording materials, which are photographically inactive, which do not contain photographically inactive impurities and which is compatible with image-wise heating with a thermal head when incorporated into the outermost layer of substantially light-insensitive thermographic recording materials.
ULTRAVON™ W, an anionic alkyl-, benzyl-benzimidazole-sulfonic acid surfactant produced by Ciba, fulfils these requirements, except that being a mixture of at least 25 components it has variable properties and also often contains photographically active impurities, which have to be removed or rendered non-photographically active prior to use. Furthermore, it is no longer available.
ASPECTS OF THE INVENTION
It is therefore an aspect of the present invention to provide a surfactant with excellent latex-stabilizing properties.
It is therefore a further aspect of the present invention to provide a photographically inactive surfactant.
It is therefore also an aspect of the present invention to provide a photographically inactive surfactant without photographically active impurities.
It is therefore also an aspect of the present invention to provide a surfactant, which enhances the adhesion of hydrophilic layers to hydrophobic supports.
It is therefore also an aspect of the present invention to provide a surfactant, which is compatible with image-wise heating with a thermal head when incorporated into the outermost layer of substantially light-insensitive thermographic recording materials.
Further aspects and advantages of the invention will become apparent from the description hereinafter.
SUMMARY OF THE INVENTION
It has been surprisingly found that a compound represented by formula (I):
a compound represented by formula (II):
or a mixture of at least one compound represented by formula (I) and at least one compound represented by formula (II), wherein M is hydrogen, an alkali atom or an ammonium group; R
1
is hydrogen, a —CH
2
)
m
SO
3
M group or a
group; R
2
is an alkyl-, alkenyl- or alkynyl-group having 6 to 25 carbon atoms; and m is an integer between 1 and 5; exhibits excellent latex-stabilizing properties, enhances the adhesion of hydrophilic layers to hydrophobic supports, such as polyethylene terephthalate and hydrophobic thermosensitive elements of substantially light-insensitive thermographic recording materials, is photographically inactive and does not contain photographically inactive impurities. Furthermore, outermost layers of substantially light-insensitive thermographic recording materials containing compounds represented by formula (I), compounds represented by formula (II) or mixtures of at least one compound represented by formula (I) with at least one compound represented by formula (II) in which n is 12 to 24 surprisingly exhibit compatibility regarding transport properties with image-wise heating with a thermal head.
Aspects of the present invention are realized by a compound represented by formula (I):
a compound represented by formula (II):
or a mixture of at least one compound represented by formula (I) with at least one compound represented by formula (II), wherein M is hydrogen, an alkali atom or an ammonium group; R
1
is hydrogen, a —(CH
2
)
m
SO
3
M group or a
group; R
2
is an alkyl-, alkenyl- or alkynyl-group having 6 to 25 carbon atoms; and m is an integer between 1 and 5.
Aspects of the present invention are also realized by the use of at least one compound represented by the above-mentioned formula (I) at least one compound represented by the above-mentioned formula (II) or a mixture of at least one compound represented by the above-mentioned formula (I) and at least one compound represented by the above-mentioned formula (II) as a surfactant.
Aspects of the present inventio
Andries Hartwig
Thillo Etienne Van
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