3-Arylbenzofuranones with electron-withdrawing substituents...

Details 3-Arylbenzofuranones with electron-withdrawing substituents... 3-Arylbenzofuranones with electron-withdrawing substituents...

2002-08-12

2004-10-26

Lambkin, Deborah C. (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S305000, C549S304000, C524S107000, C430S440000, C430S223000

Reexamination Certificate

active

06809208

ABSTRACT:

The present invention relates to novel 3-arylbenzofuranones, to compositions comprising an organic material, preferably a polymer or a lubricant, and to the novel stabilizers, as well as to the use thereof for stabilizing organic materials against oxidative, thermal or light-induced degradation and to the use of the novel stabilizers as scavengers for the oxidized developer (also termed hereafter Dox scavengers) in color photographic material.
It is well known that one of the problems associated with color photography is the diffusion of the oxidized color developer away from the light sensitive silver halide emulsion layer in which it is formed into another silver halide emulsion layer, which can result in the formation of unwanted dyes at undesired places. For instance, while being generated in the green sensitive layer and forming a magenta dye through a coupling reaction with the incorporated magenta coupler, the oxidized developer can also diffuse to the red sensitive layer thereby producing unwanted cyan dye or to the blue sensitive layer thereby producing unwanted yellow dye. This kind of color formation in the wrong layers will damage the color balance of the photographic image and thus results in poor color reproduction. One way of circumventing this problem is to incorporate oxidized developer scavengers in interlayers between the light sensitive silver halide emulsion layers. These scavengers should have additional properties such as low tendency to migrate, good stability towards aerial oxidation and high solubility in photographic oils.
Hydroquinone derivatives which are useful as scavengers for oxidized developers are for example described in U.S. Pat. No. 4,345,016.
The use of some 3-phenyl-3H-benzofuran-2-ones as stabilizers for organic polymers is disclosed, inter alia in WO-A-80/01566 and U.S. Pat. No. 5,516,920.
It has now been found that a selected group of 3-arylbenzofuran-2-ones with electron-withdrawing substituents is particularly suitable for use as stabilizers for organic materials that are susceptible to oxidative, thermal or light-induced degradation. These new compounds are also particularly suitable as Dox scavengers in color photographic material.
Accordingly, the invention relates to compounds of the formula I
wherein, when n is 1,
R
1
is a radical of the formula II, III or IV
 and
when n is 2,
R
1
is
R
2
, R
3
, R
4
and R
5
are each independently of one another hydrogen, chloro, hydroxyl, C
1
-C
25
alkyl, C
7
-C
9
phenylalkyl, unsubstituted or C
1
-C
4
alkyl-substituted phenyl; unsubstituted or C
1
-C
4
alkyl-substituted C
5
-C
8
cycloalkyl; C
1
-C
18
alkoxy, C
1
-C
18
alkylthio, C
1
-C
4
alkylamino, di-(C
1
-C
4
alkyl)amino, C
1
-C
25
alkanoyloxy, C
1
-C
25
alkanoylamino, C
3
-C
25
alkenoyloxy, C
3
-C
25
alkanoyloxy which is interrupted by oxygen, sulfur or
 C
6
-C
9
cycloalkylcarbonyloxy, benzoyloxy or C
1
-C
12
alkyl-substituted benzoyloxy; or each pair of substituents R
2
and R
3
or R
3
and R
4
or R
4
and R
5
together with the linking carbon atoms, forms a benzene ring; or R
4
is additionally —(CH
2
)
p
—COR
19
or —(CH
2
)
q
OH, or when R
3
, R
5
and R
6
are hydrogen, R
4
is additionally a radical of the formula V
 wherein R
1
is as defined above for n=1,
R
6
is hydrogen or a radical of the formula VI
 in which R
4
is not a radical of the formula V and R
1
is as defined above for n=1,
R
7
, R
8
, R
9
, R
10
, R
11
, R
12
, R
13
, R
14
and R
15
are each independently of one another hydrogen, fluoro, fluoro-substituted C
1
-C
12
alkyl; —CN,
 —SOR
26
, —SO
2
R
26
or SO
3
R
26
; with the proviso that at least one of R
7
, R
8
, R
9
, R
10
, R
11
, R
12
, R
13
, R
14
or R
15
is not hydrogen,
R
16
and R
17
are each independently of one another phenylene or naphthylene which are substituted by fluoro, fluoro-substituted C
1
-C
12
alkyl, —CN,
 —SOR
26
, —SO
2
R
26
or SO
3
R
26
,
R
18
is hydrogen or C
1
-C
8
alkyl,
R
19
is hydroxyl,
 C
1
-C
18
alkoxy or
R
20
and R
21
are each independently of one another hydrogen, CF
3
, C
1
-C
12
alkyl or phenyl, or R
20
and R
21
together with the linking carbon atom, form a C
5
-C
8
cycloalkylidene ring which is unsubstituted or substituted by 1 to 3 C
1
-C
4
alkyl groups;
R
22
is hydrogen, hydroxyl,
 C
1
-C
25
alkyl, C
7
-C
9
phenylalkyl, unsubstituted or C
1
-C
4
alkyl-substituted phenyl; unsubstituted or C
1
-C
4
alkyl-substituted C
5
-C
8
cycloalkyl; or
C
3
-C
25
alkyl which is interrupted by oxygen, sulfur or
R
23
is C
1
-C
25
alkyl, C
7
-C
9
phenylalkyl, unsubstituted or C
1
-C
4
alkyl-substituted phenyl; unsubstituted or C
1
-C
4
alkyl-substituted C
5
-C
8
cycloalkyl; or C
3
-C
25
alkyl which is interrupted by oxygen, sulfur or
R
24
and R
25
are each independently of one another hydrogen, C
1
-C
25
alkyl, hydroxyl-substituted C
2
-C
24
alkyl; C
3
-C
25
alkyl which is interrupted by oxygen, sulfur or
 phenylalkyl which is unsubstituted or is substituted on the phenyl ring by C
1
-C
4
alkyl; or C
3
-C
24
alkenyl; or R
24
and R
25
, together with the nitrogen atom to which they are attached, form a 5-, 6- or 7-membered heterocyclic ring which is unsubstituted or is substituted by C
1
-C
4
alkyl or is interrupted by oxygen, sulfur or
R
26
is hydrogen or C
1
-C
25
alkyl,
R
27
and R
28
are each independently of one another hydrogen, C
1
-C
25
alkyl, hydroxyl-substituted C
2
-C
24
alkyl; C
3
-C
25
alkyl which is interrupted by oxygen, sulfur or
 C
7
-C
9
phenylalkyl which is unsubstituted or is substituted on the phenyl ring by C
1
-C
4
alkyl; or C
3
-C
24
alkenyl; or R
27
and R
28
, together with the nitrogen atom to which they are attached, form a 5-, 6- or 7-membered heterocyclic ring which is unsubstituted or is substituted by C
1
-C
4
alkyl or is interrupted by oxygen, sulfur or
R
29
and R
30
are each independently of one another hydrogen, C
1
-C
18
alkyl or C
7
-C
9
phenylalkyl, or R
29
and R
30
together with the nitrogen atom to which they are attached form a 5-, 6- or 7-membered heterocyclic ring which is unsubstituted or is substituted by C
1
-C
4
alkyl or is interrupted by oxygen, sulfur or
X
1
is a direct bond, C
1
-C
18
alkylene, C
2
-C
18
alkylene which is interrupted by oxygen, sulfur or
 C
2
-C
18
alkenylene, C
2
-C
20
alkylidene, C
7
-C
20
phenylalkylidene, C
5
-C
8
cycloalkylene, C
7
-C
8
bicycloalkylene, unsubstituted or C
1
-C
4
alkyl-substituted phenylene,
 or —O—X
3
—O—,
X
2
is C
2
-C
18
alkylene, C
4
-C
18
alkylene which is interrupted by oxygen, sulfur or
 C
2
-C
18
alkenylene, C
5
-C
8
cycloalkylene, C
7
-C
8
bicycloalkylene, unsubstituted or C
1
-C
4
alkyl-substituted phenylene,
X
3
is C
2
-C
18
alkylene, C
4
-C
18
alkylene which is interrupted by oxygen, sulfur or
 C
2
-C
18
alkenylene, C
5
-C
8
cycloalkylene, C
7
-C
8
bicycloalkylene, unsubstituted or C
1
-C
4
alkyl-substituted phenylene,
M is a metal cation of valency r,
n is 1 or 2,
p is 0, 1 or 2,
q is 1, 2, 3, 4, 5 or 6, and
r is 1, 2 or 3.
Alkanoyloxy having up to 25 carbon atoms is a branched or unbranched radical, for example formyloxy, acetoxy, propionyloxy, butanoyloxy, pentanoyloxy, hexanoyloxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy, undecanoyloxy, dodecanoyloxy, tridecanoyloxy, tetradecanoyloxy, pentadecanoyloxy, hexadecanoyloxy, heptadecanoyloxy, octadecanoyloxy, icosanoyloxy or docosanoyloxy. Preference is given to alkanoyloxy having from 2 to 18, especially from 2 to 12, e.g. from 2 to 6, carbon atoms. Special preference is given to acetoxy.
C
3
-C
25
Alkanoyloxy interrupted by oxygen, sulfur or by
is, for example, CH
3
—O—CH
2
COO—, CH
3
—S—CH
2
COO—, CH
3
—N(CH
3
)—CH
2
COO—, CH
3
—O—CH
2
CH
2
—O—CH
2
COO—, CH
3
—(O—CH
2
CH
2
—)
2
O—CH
2
COO—, CH
3
—(O—CH
2
CH
2
—)
3
O—CH
2
COO— or CH
3
—(O—CH
2
CH
2
—)
4
O—CH
2
COO—.
C
6
-C
9
Cycloalkylcarbonyloxy is, for example, cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, cycloheptylcarbonyloxy or cyclooctylcarbonyloxy. Preference is given to cyclohexylcarbonyloxy.
C
3
-C
25
Alkenoyloxy interrupted by oxygen, sul

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