3-Arylbenzofuranones as stabilizers

Details 3-Arylbenzofuranones as stabilizers 3-Arylbenzofuranones as stabilizers

2000-04-20

2002-02-12

Ramsuer, Robert W. (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C524S084000, C524S107000, C524S109000, C524S111000

Reexamination Certificate

active

06346630

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 stabilisers, as well as to the use thereof for stabilising organic materials against oxidative, thermal or light-induced degradation.
Individual 3-arylbenzofuran-2-ones are known in the literature and have been described, inter alia, by J. Morvan et al., Bull. Soc. Chim. Fr. 1979, 583.
The use of some 3-phenyl-3H-benzofuran-2ones as stabilisers for organic polymers is disclosed, inter alia in U.S. Pat. No. 4,325,863; U.S. Pat. No. 4,338,244 and U.S. Pat. No. 5,175,312.
It has now been found that a selected group of 3-arylbenzofuran-2-ones is particularly suitable for use as stabilisers for organic materials that are susceptible to oxidative, thermal or light-induced degradation.
Accordingly, the invention relates to compounds of formula I
wherein, when n is 1,
R
1
is naphthyl, phenanthryl, anthryl, 5,6,7,8-tetrahydro-2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, thienyl, benzo[b]thienyl, naphtho[2,3-b]thieyl, thiathrenyl, dibenzofuryl, chromenyl, xanthenyl, phenoxathiinyl, pyrrolyl, imidazolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolizinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolizinyl, isoquinolyl, quinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, pteridinyl, carbazolyl, &bgr;-carbolinyl, phenanthridinyl, acridinyl, perimidinyl, phenanthrolinyl, phenazinyl, isothiazolyl, phenothiazinyl, isoxazolyl, furazanyl, biphenyl, terphenyl, fluorenyl or phenoxazinyl, each unsubstituted or substituted by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, hydroxy, halogen, amino, C
1
-C
4
alkylamino, phenylamino or di(C
1
-C
4
alkyl)amino, or R
1
is a radical of formula II
and
when n is 2
R
1
is phenylene or naphthylene which is unsubstituted or substituted by C
1
-C
4
alkyl or hydroxy; or is —R
12
—X—R
13
—,
R
2
, R
3
, R
4
and R
5
are each independently of one another hydrogen, chloro, hydroxy, 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
8
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 N—R
14
; C
6
-C
8
cycloalkylcarbonyloxy, benzoyloxy or C
1
-C
12
alkyl-substituted benzoyloxy; with the proviso that, when R
2
is hydrogen or methyl, R
7
or R
9
is not hydroxy or C
1
-C
25
alkanoyloxy, 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; R
4
is additionally —(CH
2
)
p
—COR
15
or —(CH
2
)
q
OH, or when R
3
, R
5
and R
6
are hydrogen, R
4
is additionally a radical of formula III
wherein R
1
is as defined above for n=1,
R
6
is hydrogen or a radical of formula IV
in which R
4
is not a radical of formula III and R
1
is as defined above for n=1, R
7
, R
8
, R
9
and R
10
are each independently of one another hydrogen, halogen, hydroxy, C
1
-C
25
alkyl, C
2
-C
25
alkyl which is interrupted by oxygen, sulfur or N—R
14
; C
1
-C
25
-alkoxy, C
2
-C
25
alkoxy which is interrupted by oxygen, sulfur or N—R
14
; C
1
-C
25
alkylthio, C
3
-C
25
alkenyl, C
3
-C
25
alkenyloxy, C
3
-C
25
alkynyl, C
3
-C
25
alkynyloxy, C
7
-C
9
phenylalkyl, C
7
-C
9
phenylalkoxy, unsubstituted or C
1
-C
4
alkyl-substituted phenyl; unsubstituted or C
1
-C
4
alkyl-substituted phenoxy; unsubstituted or C
1
-C
4
alkyl-substituted C
5
-C
8
cycloalkyl; unsubstituted or C
1
-C
4
alkyl-substituted C
5
-C
8
cycloalkoxy; C
1
-C
4
alkylamino, di(C
1
-C
4
alkyl)amino, C
1
-C
25
alkanoyl, C
3
-C
25
alkanoyl which is interrupted by oxygen, sulfur or N—R
14
; C
1
-C
25
alkanoyloxy, C
3
-C
25
alkanoyloxy which is interrupted by oxygen, sulfur or N—R
14
; C
1
-C
25
alkanoylamino, C
3
-C
25
alkenoyl, C
3
-C
25
alkenoyl which is interrupted by oxygen, sulfur or N—R
14
; C
3
-C
25
alkenoyloxy which is interrupted by oxygen, sulfur or N—R
14
; C
6
-C
9
cycloalkylcarbonyl, C
6
-C
9
cycloalkylcarbonyloxy, benzoyl or C
1
-C
12
alkyl-substituted benzoyl; benzoyloxy or C
1
-C
12
alkyl-substituted benzoyloxy;
or also in formula II each pair of substitutents R
7
and R
8
or R
8
and R
11
, together with the linking carbon atoms, forms a benzene ring,
R
11
is hydrogen, C
1
-C
25
alkyl, C
1
-C
25
alkylthio, C
3
-C
25
alkenyl, C
3
-C
25
alkynyl, 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
4
alkylamino, di(C
1
-C
4
alkyl)amino, C
1
-C
25
alkanoyl, C
3
-C
25
alkanoyl which is interrupted by oxygen, sulfur or N—R
14
; C
1
-C
25
alkanoylamino, C
3
-C
25
alkenoyl, C
3
-C
25
alkenoyl which is interrupted by oxygen, sulfur or N—R
14
; C
6
-C
9
cycloalkylcarbonyl, benzoyl or C
1
-C
12
alkyl-substituted benzoyl; with the proviso that at least one of R
7
, R
8
, R
9
, R
10
or R
11
is not hydrogen, R
12
and R
13
are each independently of the other unsubstituted or C
1
-C
4
alkyl-substituted phenylene or naphthylene,
R
14
is hydrogen or C
1
-C
8
alkyl,
R
15
is hydroxy,
R
16
and R
17
are each independently of the other hydrogen CF
3
, C
1
-C
12
alkyl or phenyl, or
R
16
and R
17
, 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
18
and R
19
are each independently of the other hydrogen, C
1
-C
4
alkyl or phenyl,
R
20
is hydrogen or C
1
-C
4
alkyl,
R
21
is hydrogen, unsubstituted or C
1
C
4
alkyl-substituted phenyl; C
1
-C
25
alkyl, C
2
-C
25
alkyl which is interrupted by oxygen, sulfur or N—R
14
; C
7
-C
9
phenylalkyl which is unsubstituted or substituted in the phenyl moiety by 1 to 3 C
1
-C
4
alkyl groups; C
7
-C
25
phenylalkyl which is interrupted by oxygen, sulfur or N—R
14
and which is unsubstituted or substituted in the phenyl moiety by 1 to 3 C
1
-C
4
alkyl groups; or R
20
and R
21
, together with the linking carbon atoms, form a C
5
-C
12
cycloalkylidene ring which is unsubstituted or substituted by 1 to 3 C
1
-C
4
alkyl groups;
R
22
is hydrogen or C
1
-C
4
alkyl,
R
23
is hydrogen, C
1
-C
25
alkanoyl, C
3
-C
25
alkenoyl, C
3
-C
25
alkanoyl which is interrupted by oxygen, sulfur or N—R
14
; C
2
-C
25
alkanoyl which is substituted by a di(C
1
-C
6
alkyl)phosphonate group; C
6
-C
9
cycloalkylcarbonyl, thenoyl, furoyl, benzoyl or C
1
-C
12
alkyl-substituted benzoyl;
R
24
and R
25
are each independently of the other hydrogen or C
1
-C
18
alkyl,
R
26
is hydrogen or C
1
-C
8
alkyl,
R
27
is a direct bond, C
1
C
18
alkylene, C
2
-C
18
alkylene which is interrupted by oxygen, sulfur or N—R
14
; 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,
R
28
is hydroxy,
R
29
is oxygen —NH— or
R
30
is C
1
-C
8
alkyl or phenyl,
R
31
is hydrogen or C
1
-C
18
alkyl,
M is a metal cation of valency r,
X is a direct bond, oxygen, sulfur or —NR
31
—,
N is 1 or 2
p 0, 1 or 2,
q is 1,2,3,4,5 or 6
r is 1,2 or 3, and
s is 0, 1 or 2
Naphthyl, phenanthryl, anthryl, 5,6,7,8-tetrahydro-2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, thienyl, benzo[b]thienyl, naphtho[2,3-b]thienyl, thiathrenyl, dibenzofuryl, chromenyl, xanthenyl, phenoxathiinyl, pyrrolyl, imidazolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolizinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolizinyl, isoquinolyl, quinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, pteridinyl, carbazolyl, &bgr;-carbolinyl, phenanthridinyl, acridinyl, perimidinyl, phenanthrolinyl, phenazinyl, isothiazolyl, phenothiazinyl, isoxazolyl, furazanyl, biphenyl, terphenyl, fluorenyl or phenoxazinyl, each unsubstituted or substituted by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, hydroxy, halogen, amino, C
1
-C
4

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