US 5,428,162 AGranted

3-(2-acyloxyethoxyphenyl)benzofuran-2-ones for use as stabilizers

AssigneeCiba-Geigy Corporation

InventorPeter Nesvadba

Life of this patent

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Abstract

Novel compounds of the formula (1), ##STR1## in which R.sub.1 is hydrogen or acyl, R.sub.2 to R.sub.5 are independently hydrogen, chloro, alkyl phenylalkyl, aryl, cycloalkyl, alkoxy, alkylthio, hydroxy, amino or substituted amino, R.sub.6 is hydrogen, R.sub.7 to R.sub.10 are independently hydrogen, alkyl or alkoxy, R.sub.17 or R.sub.19 is hydrogen or alkyl, and R.sub.18 is hydrogen, alkyl, aralkyl or aryl, are described for use as stabilizers for organic materials against thermal, oxidative or light-induced degradation.

Claims14

Dependent claims

A compound of the formula (1) ##STR105## in which, when m is 1, R.sub.1 is hydrogen C.sub.1 -C.sub.25 alkanoyl C.sub.3 -C.sub.25 alkenoyl C.sub.3 -C.sub.25 alkanoyl which is interrupted by oxygen, sulfur or ##STR106## C.sub.2 -C.sub.25 alkanoyl substituted by a di(C.sub.1 -C.sub.6 alkyl)phosphonate group;

C.sub.6 -C.sub.9 cycloalkylcarbonyl, thenoyl, furoyl, benzoyl or C.sub.1 -C.sub.12 alkyl-substituted benzoyl;
##STR107## and, when m is 2,
R.sub.1 is ##STR108## and, m is 3,
R.sub.1 is C.sub.4 -C.sub.18 alkanetricarbonyl, C.sub.9 -C.sub.18 aryltricarbonyl, ##STR109## and, when m is 4,
R.sub.1 is C.sub.6 .about.C.sub.18 alkanetetracarbonyl or C.sub.10 -C.sub.18 aryltetracarbonyl,
R.sub.2, R.sub.3, R.sub.4 and R.sub.5, independently of one another, are hydrogen, chlorine, C.sub.1 -C.sub.25 alkyl,
C.sub.7 -C.sub.9 phenylalkyl, unsubstituted or C.sub.1 -C.sub.4 alkyl-substituted phenyl, unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted C.sub.5 -C.sub.8 cycloalkyl;
C.sub.1 -C.sub.18 alkoxy, C.sub.1 -C.sub.18 alkylthio, hydroxyl, C.sub.1 -C.sub.4 alkylamino, di(C.sub.1 -C.sub.4 -alkyl)amino, C.sub.1 -C.sub.25 alkanoyloxy, C.sub.1 -C.sub.25 alkanoylamino, C.sub.3 -C.sub.25 alkenoyloxy, C.sub.3 -C.sub.25 alkanoyloxy which is interrupted by oxygen, sulfur or ##STR110## C.sub.6 -C.sub.9 cycloalkylcarbonyloxy, benzoyloxy or C.sub.1 -C.sub.2 alkyl-substituted benzoyloxy, or, furthermore, the radicals R.sub.2 and R.sub.3 or the radicals R.sub.3 and R.sub.4 or the radicals R.sub.4 and R.sub.5 together with the carbon atoms to which they are attached form a phenyl ring, R.sub.4 is additionally --(CH.sub.2).sub.n --COR.sub.11, or, when R.sub.3, R.sub.5, R.sub.6, R.sub.7 and R.sub.10 are hydrogen, R.sub.4 is additionally a radical of the formula (2) ##STR111## in which R.sub.1 is as defined above for m=1, R.sub.6 is hydrogen or a radical of the formula (3) ##STR112## in which R.sub.4 is not a radical of the formula (2) and R.sub.l is as deemed above for m=1,
R.sub.7, R.sub.8, R.sub.9 and R.sub.10, independently of one another, are hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, on the condition that at least one of the radicals R.sub.7, R.sub.8, R.sub.9 and R.sub.10 is hydrogen,
R.sub.11 is hydroxyl, ##STR113## R.sub.12 and R.sub.13, independently of one another, are hydrogen, CF.sub.3, C.sub.1 -C.sub.12 alkyl or phenyl, or
R.sub.12 and R.sub.13 together with the carbon atom to which they are attached form a C.sub.5 -C.sub.8 cycloalkylidene ring which is unsubstituted or substituted by 1 to 3 C.sub.1 -C.sub.4 alkyl groups;
R.sub.14 and R.sub.15 independently of one another, are hydrogen or C.sub.1 -C.sub.18 alkyl,
R.sub.16 is hydrogen or C.sub.1 -C.sub.8 alkyl,
R.sub.17 is hydrogen or C.sub.1 -C.sub.4 alkyl,
R.sub.18 is hydrogen, unsubstituted or C.sub.1 -C.sub.4 alkyl-substituted phenyl;
C.sub.1 -C.sub.25 alkyl, C.sub.2 -C.sub.25 alkyl which is interrupted by oxygen, sulfur or ##STR114## C.sub.7 -C.sub.9 phenylalkyl which is unsubstituted or substituted on the phenyl radical by 1 to 3 C.sub.1 -C.sub.4 alkyl groups;
C.sub.7 -C.sub.25 phenylalkyl which is interrupted by oxygen, sulfur or ##STR115## and unsubstituted or substituted on the phenyl radical by 1 to 3 C.sub.1 -C.sub.4 alkyl groups, or, furthermore, the radicals R.sub.17 and R.sub.18 together with the carbon atoms to which they are attached form a C.sub.5 -C.sub.12 cycloalkylene ring which is unsubstituted or substituted by 1 to 3 C.sub.1 -C.sub.4 alkyl groups;
or, when R.sub.6, R.sub.17 and R.sub.19 are hydrogen, R.sub.4 is not a radical of the formula (2), m is 1 and R.sub.1 is as defined above for m=1, R.sub.18 is additionally a radical of the formula (4) ##STR116## R.sub.19 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.20 is hydrogen or C.sub.1 -C.sub.4 alkyl,
R.sub.21 is a direct bond, C.sub.1 -C.sub.18 alkylene, C.sub.2 -C.sub.18 alkylene which is interrupted by oxygen, sulfur or ##STR117## C.sub.2 -C.sub.18 alkenylene, C.sub.2 -C.sub.20 alkylidene, C.sub.7 -C.sub.20 phenylalkylidene, C.sub.5 -C.sub.8 -cycloalkylene, C.sub.7 -C.sub.8 bicycloalkylene, unsubstituted or C.sub.1 -C.sub.4 alkyl-substituted phenylene, ##STR118## R.sub.22 is oxygen, --NH-- or ##STR119## R.sub.23 is C.sub.1 -C.sub.18 alkyl or phenyl, R.sub.24 is C.sub.2 -C.sub.18 alkylene, C.sub.5 -C.sub.8 cycloalkylene or phenylene,
R.sub.25 is a direct bond, C.sub.1 -C.sub.18 alkylene or C.sub.2 -C.sub.18 alkylene which is interrupted by oxygen, sulfur or ##STR120## M is an r-valent metal cation, m is 1, 2, 3 or 4, R.sub.6 being hydrogen if m is 2, 3 or 4;
n is 0, 1 or 2 and
r is 1, 2 or 3.

19 more elements

A compound of the formula (9) ##STR131## in which R.sub.7, R.sub.8, R.sub.9 and R.sub.10, independently of one another, are hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, on the condition that at least one of the radicals R.sub.7, R.sub.8, R.sub.9 and R.sub.10 is hydrogen and, when R.sub.7, R.sub.8, R.sub.9 and R.sub.10 are simultaneously hydrogen, either R.sub.17, R.sub.18 or R.sub.19 is different from hydrogen,

R.sub.16 is hydrogen or C.sub.1 -C.sub.8 alkyl,
R.sub.17 is hydrogen or C.sub.1 -C.sub.4 alkyl,
R.sub.18 is hydrogen, unsubstituted or C.sub.1 -C.sub.4 alkyl-substituted phenyl;
C.sub.2 -C.sub.25 alkyl, C.sub.2 -C.sub.25 alkyl which is interrupted by oxygen or sulfur;
C.sub.7 -C.sub.9 phenylalkyl which is unsubstituted or substituted on the phenyl ring by 1 to 3 C.sub.1 -C.sub.4 alkyl groups;
C.sub.7 -C.sub.25 phenylalkyl which is interrupted by oxygen, sulfur or ##STR132## and unsubstituted or substituted on the phenyl ring by 1 to 3 C.sub.1 -C.sub.4 alkyl groups, or, furthermore, the radicals R.sub.17 and R.sub.18 together with the carbon atoms to which they are attached form a C.sub.5 -C.sub.12 cycloalkylene ring which is unsubstituted or substituted by 1 to 3 C.sub.3 -C.sub.4 alkyl groups;
or, when R.sub.17 and R.sub.19 are hydrogen, R.sub.18.sup.1 is additionally a radical of the formula (10) ##STR133## R.sub.19 is hydrogen or C.sub.1 -C.sub.4 alkyl, and R.sub.25 is a direct bond, C.sub.1 -C.sub.18 alkylene or C.sub.2 -C.sub.18 alkylene which is interrupted by oxygen, sulfur or ##STR134##

4 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/124,139Filed 20 Sep 1993
Priority: CH 2979/9223 Sep 1992
Granted: 27 Jun 1995
Term ends: Not estimatedThe source records don’t support an estimate.

Classification10 codes

C07D 307/83
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…
C07C 59/64
Containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups:…
C07F 9/65517
The oxygen atom being part of a five-membered ring: condensed with carbocyclic rings or carbocyclic ring systems
C08K 5/1535
Having one oxygen atom in the ring: five-membered rings

Family

No related US applications are recorded in the indexed filing history.

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Abstract

C.sub.6 -C.sub.9 cycloalkylcarbonyl, thenoyl, furoyl, benzoyl or C.sub.1 -C.sub.12 alkyl-substituted benzoyl;
##STR107## and, when m is 2,
R.sub.1 is ##STR108## and, m is 3,
R.sub.1 is C.sub.4 -C.sub.18 alkanetricarbonyl, C.sub.9 -C.sub.18 aryltricarbonyl, ##STR109## and, when m is 4,
R.sub.1 is C.sub.6 .about.C.sub.18 alkanetetracarbonyl or C.sub.10 -C.sub.18 aryltetracarbonyl,
R.sub.2, R.sub.3, R.sub.4 and R.sub.5, independently of one another, are hydrogen, chlorine, C.sub.1 -C.sub.25 alkyl,
C.sub.7 -C.sub.9 phenylalkyl, unsubstituted or C.sub.1 -C.sub.4 alkyl-substituted phenyl, unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted C.sub.5 -C.sub.8 cycloalkyl;
C.sub.1 -C.sub.18 alkoxy, C.sub.1 -C.sub.18 alkylthio, hydroxyl, C.sub.1 -C.sub.4 alkylamino, di(C.sub.1 -C.sub.4 -alkyl)amino, C.sub.1 -C.sub.25 alkanoyloxy, C.sub.1 -C.sub.25 alkanoylamino, C.sub.3 -C.sub.25 alkenoyloxy, C.sub.3 -C.sub.25 alkanoyloxy which is interrupted by oxygen, sulfur or ##STR110## C.sub.6 -C.sub.9 cycloalkylcarbonyloxy, benzoyloxy or C.sub.1 -C.sub.2 alkyl-substituted benzoyloxy, or, furthermore, the radicals R.sub.2 and R.sub.3 or the radicals R.sub.3 and R.sub.4 or the radicals R.sub.4 and R.sub.5 together with the carbon atoms to which they are attached form a phenyl ring, R.sub.4 is additionally --(CH.sub.2).sub.n --COR.sub.11, or, when R.sub.3, R.sub.5, R.sub.6, R.sub.7 and R.sub.10 are hydrogen, R.sub.4 is additionally a radical of the formula (2) ##STR111## in which R.sub.1 is as defined above for m=1, R.sub.6 is hydrogen or a radical of the formula (3) ##STR112## in which R.sub.4 is not a radical of the formula (2) and R.sub.l is as deemed above for m=1,
R.sub.7, R.sub.8, R.sub.9 and R.sub.10, independently of one another, are hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, on the condition that at least one of the radicals R.sub.7, R.sub.8, R.sub.9 and R.sub.10 is hydrogen,
R.sub.11 is hydroxyl, ##STR113## R.sub.12 and R.sub.13, independently of one another, are hydrogen, CF.sub.3, C.sub.1 -C.sub.12 alkyl or phenyl, or
R.sub.12 and R.sub.13 together with the carbon atom to which they are attached form a C.sub.5 -C.sub.8 cycloalkylidene ring which is unsubstituted or substituted by 1 to 3 C.sub.1 -C.sub.4 alkyl groups;
R.sub.14 and R.sub.15 independently of one another, are hydrogen or C.sub.1 -C.sub.18 alkyl,
R.sub.16 is hydrogen or C.sub.1 -C.sub.8 alkyl,
R.sub.17 is hydrogen or C.sub.1 -C.sub.4 alkyl,
R.sub.18 is hydrogen, unsubstituted or C.sub.1 -C.sub.4 alkyl-substituted phenyl;
C.sub.1 -C.sub.25 alkyl, C.sub.2 -C.sub.25 alkyl which is interrupted by oxygen, sulfur or ##STR114## C.sub.7 -C.sub.9 phenylalkyl which is unsubstituted or substituted on the phenyl radical by 1 to 3 C.sub.1 -C.sub.4 alkyl groups;
C.sub.7 -C.sub.25 phenylalkyl which is interrupted by oxygen, sulfur or ##STR115## and unsubstituted or substituted on the phenyl radical by 1 to 3 C.sub.1 -C.sub.4 alkyl groups, or, furthermore, the radicals R.sub.17 and R.sub.18 together with the carbon atoms to which they are attached form a C.sub.5 -C.sub.12 cycloalkylene ring which is unsubstituted or substituted by 1 to 3 C.sub.1 -C.sub.4 alkyl groups;
or, when R.sub.6, R.sub.17 and R.sub.19 are hydrogen, R.sub.4 is not a radical of the formula (2), m is 1 and R.sub.1 is as defined above for m=1, R.sub.18 is additionally a radical of the formula (4) ##STR116## R.sub.19 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.20 is hydrogen or C.sub.1 -C.sub.4 alkyl,
R.sub.21 is a direct bond, C.sub.1 -C.sub.18 alkylene, C.sub.2 -C.sub.18 alkylene which is interrupted by oxygen, sulfur or ##STR117## C.sub.2 -C.sub.18 alkenylene, C.sub.2 -C.sub.20 alkylidene, C.sub.7 -C.sub.20 phenylalkylidene, C.sub.5 -C.sub.8 -cycloalkylene, C.sub.7 -C.sub.8 bicycloalkylene, unsubstituted or C.sub.1 -C.sub.4 alkyl-substituted phenylene, ##STR118## R.sub.22 is oxygen, --NH-- or ##STR119## R.sub.23 is C.sub.1 -C.sub.18 alkyl or phenyl, R.sub.24 is C.sub.2 -C.sub.18 alkylene, C.sub.5 -C.sub.8 cycloalkylene or phenylene,
R.sub.25 is a direct bond, C.sub.1 -C.sub.18 alkylene or C.sub.2 -C.sub.18 alkylene which is interrupted by oxygen, sulfur or ##STR120## M is an r-valent metal cation, m is 1, 2, 3 or 4, R.sub.6 being hydrogen if m is 2, 3 or 4;
n is 0, 1 or 2 and
r is 1, 2 or 3.

19 more elements

Facts

Application

08/124,139Filed 20 Sep 1993

Priority

CH 2979/9223 Sep 1992

Granted

27 Jun 1995

Term ends

Not estimatedThe source records don’t support an estimate.

Classification10 codes

C07D 307/83
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…
C07C 59/64
Containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups:…
C07F 9/65517
The oxygen atom being part of a five-membered ring: condensed with carbocyclic rings or carbocyclic ring systems
C08K 5/1535
Having one oxygen atom in the ring: five-membered rings