# US 5,710,198 A · Cyclic diphenylacetonitriles as stabilizers

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- Number: US 5,710,198 A
- Document ID: US5710198A
- Status: Granted
- Kind: A
- Application number: 08/662,108
- Filed: 1996-06-14
- Granted: 1998-01-20
- Earliest claimed: 1993-01-18
- Assignees: Ciba Specialty Chemicals Corporation
- Inventors: Rita Pitteloud
- Web page: https://patentgrep.com/patent/US5710198A

## CPC

- C08K 5/3437: condensed with carbocyclic rings
- C07C 255/47: to carbon atoms of rings being part of condensed ring systems
- C07D 219/04: 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, directly attached to carbon atoms of the ring system
- C07D 311/84: 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, directly attached in position 9
- C07D 335/14: 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, directly attached in position 9
- C08K 5/1545: Six-membered rings
- C08K 5/315: Compounds containing carbon-to-nitrogen triple bonds
- C08K 5/45: Heterocyclic compounds having sulfur in the ring
- C07C 2603/18: Fluorenes; Hydrogenated fluorenes
- C07C 2603/32: Dibenzocycloheptenes; Hydrogenated dibenzocycloheptenes
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Compounds of the formula I ##STR1## in which the general symbols are as defined in claim 1, as stabilizers for organic materials against thermal, oxidative or light-induced degradation are described.

## Claims

### Claim 1

A composition comprising
a) an organic material subjected to oxidative, thermal or light-induced degradation and
b) an effective stabilizing amount of at least one compound of the formula I ##STR96## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 independendy of one another are hydrogen, haloge or C.sub.2 -C.sub.25 salkyl which is interrupted by oxygen, sulfur or ##STR97## C.sub.5 C.sub.8 cloalkyl which is unsubstituted or substituted by C.sub.1 C.sub.4 alkyl; phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl; C.sub.7 -C.sub.9 phenylalkyl, hydroxyl, C.sub.1 C.sub.18 alkoxy or C.sub.3 C.sub.18 alkoxy which is interrupted by oxygen, sulfur or ##STR98## mercapto, C.sub.1 -C.sub.18 alkylthio or C.sub.3 C.sub.18 alkylthio which is interrupted by oxygen, sulfur or ##STR99## C.sub.1 C.sub.25 alkanoyloxy or C.sub.3 C.sub.25 alkanoyloxy which is interrupted by oxygen, sulfur or ##STR100## C.sub.3 -C.sub.25 alkenoyloxy, benzoyloxy or benzoyloxy which is substituted by C.sub.1 C.sub.12 alkyl; nitro, cyano, --(CH.sub.2).sub.m COR.sub.11 or ##STR101## and furthermore the radicals R.sub.1 and R.sub.2, R.sub.2 and R.sub.3, R.sub.3 and R.sub.4, R.sub.5 and R.sub.6, R.sub.6 and R.sub.7 or R.sub.7 and R.sub.8, together with the carbon atoms to which they are bonded, form a benzo ring, or the same pairs of radicals together are --O(CH.sub.2).sub.n O--, with the condition that at least one of the radicals R.sub.1, R.sub.2, R.sub.3 or R.sub.4 and at least one of the radicals R.sub.5, R.sub.6, R.sub.7 or R.sub.8 is hydrogen, R is additionally a radical of the formula II, R.sub.2 is additionally a radical of the formula III, R.sub.3 is additionally a radical of the formula IV and R.sub.4 is additionally a radical of the formula V, and at the same time only one radical of the formula II, III, IV or V occurs in the compound of the formula I, ##STR102## R.sub.9 is hydrogen or a radical of the formula VI ##STR103## in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are not a radical of the formula II, III, IV or V,
R.sub.10 is hydrogen or C.sub.1 -C.sub.8 alkyl,
R.sub.11 is hydroxyl, C.sub.1 C.sub.18 alkoxy or ##STR104## R.sub.12 and R.sub.13 independendy of one another are hydrogen or C.sub.1 -C.sub.18 alkyl,
R.sub.14 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 ##STR105## R.sub.15 and R.sub.16 independenfiy of one another are hydrogen, CF.sub.3, C.sub.1 -C.sub.12 alkyl or phenyl, or R.sub.15 and R.sub.16, together with the C atom to which they are bonded, form a C.sub.5 C.sub.8 cycloalkylidene ring which is unsubstimted or substituted by 1 to 3 C.sub.1 -C.sub.4 alkyl groups,
R.sub.17 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 ##STR106## 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 bicycoalcne, phcnyenc which is unsuhsdtuted or substituted by C.sub.1 C.sub.4 alkyl, ##STR107## m is 0,1 or 2 and n is 1 or 2.

### Claim 2 (depends on 1)

A composition according to claim 1, in which
R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 independently of one another are hydrogen, chlorine C.sub.1 C.sub.18 alkyl or C.sub.2 -C.sub.18 alkyl which is interrupted by oxygen, sulfur or ##STR108## C.sub.5 C.sub.8 cycloalkyl which is unsubstituted or substituted by CFC.sub.4 alkyl; phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl; C.sub.7 -C.sub.9 phgnylalkyl, hydroxyl, C.sub.1 -C.sub.18 alkoxy or C.sub.3 -C.sub.18 alkoxy which is interrupted by oxygen, sulfur or ##STR109## mercapto, C.sub.1 -C.sub.18 alkylthio, C.sub.1 -C.sub.18 alkanoyloxy or C.sub.3 -C.sub.18 alkanoyloxy which is interrupted by oxygen, sulfur or ##STR110## C.sub.3 -C.sub.18 alkcnoyloxy, benzoyloxy or benzoyloxy which is substituted by C.sub.1 -C.sub.8 alkyl; nitro, cyano, --(CH.sub.2).sub.m COR.sub.11 or ##STR111## and furthermore the radicals R.sub.1 and R.sub.2, R.sub.2 and R.sub.3, R.sub.3 and R.sub.4, R.sub.5 and R.sub.6, R.sub.6 and R.sub.7 or R.sub.7 and R.sub.8, together with the carbon atoms to which they are bonded, form a benzo ring, or the same pairs of radicals together are --O(CH.sub.2).sub.n O--, with the condition that at least one of the radicals R.sub.1, R.sub.2, R.sub.3 or R.sub.4 and at least one of the radicals R.sub.5, R.sub.6, R.sub.7 or R.sub.8 is hydrogen, R.sub.1 is additionally a radical of the formula II, R.sub.2 is additionally a radical of the formula III, R.sub.3 is additionally a radical of the formula IV and R.sub.4 is additionally a radical of the formula V, and in which at the same time only one radical of the formula II, III, IV or V occurs in the compound of the formula I ##STR112## R.sub.11 is hydroxyl, C.sub.1 -C.sub.12 alkoxy or ##STR113## R.sub.12 and R.sub.13 independendy of one another are hydrogen or C.sub.1 -C.sub.12 alkyl,
R.sub.14 is a direct bond, C.sub.1 C.sub.12 alkylene or C.sub.2 -C.sub.12 alkylene which is interrupted by oxygen, sulfur or ##STR114## R.sub.15 and R.sub.16 independendy of one another are hydrogen, C.sub.1 -C.sub.8 alkyl or phenyl, or R.sub.15 and R.sub.16, together with the C atom to which they are bonded, form a C.sub.5 C.sub.7 cycloalkylidene ring which is unsubstituted or substituted by 1 to 3 C.sub.1 -C.sub.4 alkyl groups, and
R.sub.17 is a direct bond, C.sub.1 -C.sub.12 alkylene or C.sub.2 -C.sub.12 alkylene which is interrupted by oxygen, sulfur or ##STR115## C.sub.2 -C.sub.12 alkenylenc, C.sub.2 -C.sub.16 alkylidene, C.sub.7 -C.sub.12 phenylalkylidene, C.sub.5 C.sub.7 hdcycloalkylene, phenylene which is unsubsdtuted or substituted by C.sub.1 -C.sub.4 alkyl or ##STR116##

### Claim 3 (depends on 1)

A composition according to claim 1, in which R.sub.8, R.sub.6, R.sub.7 and R.sub.8 are hydrogen.

### Claim 4 (depends on 1)

A composition according to claim 1, in which
X is oxygen or sulfur.

### Claim 5 (depends on 1)

A composition according to claim 1, in which
R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently of one another are hydrogen, chlorine, C.sub.1 -C.sub.18 alkyl or C.sub.2 -C.sub.18 alkyl which is interrupted by oxygen; C.sub.5 C.sub.8 cycloalkyl, phenyl, C.sub.7 -C.sub.9 phenylalkyl, hydroxyl, C.sub.1 -C.sub.18 alkoxy or C.sub.3 -C.sub.18 alkoxy which is interrupted by oxygen; C.sub.1 C.sub.18 alkylthio, C.sub.1 C.sub.18 alkanoyloxy or C.sub.3 C.sub.18 alkanoyloxy which is interrupted by oxygen; C.sub.3 C.sub.18 alkenoyloxy, benzoyloxy, cyano, --(CH.sub.2).sub.m COR.sub.11 or ##STR117## with the condition that at least one of the radicals R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is hydrogen, R.sub.2 is additionally a radical of the formula III and R.sub.4 is additionally a radical of the formula V, and in which at the same time only one radical of the formula III or V occurs in the compound of the formula I ##STR118## R.sub.5, R.sub.6, R.sub.7 and R.sub.8 independently of one another are hydrogen, chlorine, C.sub.1 -C.sub.18 alkyl, C.sub.5 C.sub.8 cycloalkyl, phenyl, benzyl, hydroxyl, C.sub.1 C.sub.18 alkoxy, C.sub.1 -C.sub.18 alkylthio, C.sub.1 C.sub.18 alkanoyloxy, C.sub.3 C.sub.18 alkenoyloxy, benzoyloxy, cyano, --(CH.sub.2).sub.m COR.sub.11 or ##STR119## with the condition that at least one of the radicals R.sub.5, R.sub.6, R.sub.7 or R.sub.8 is hydrogen,
R.sub.11 is C.sub.1 C.sub.12 alkoxy or ##STR120## R.sub.12 and R.sub.13 independently of one another are hydrogen or C.sub.1 C.sub.18 alkyl,
R.sub.14 is C.sub.1 C.sub.18 alkylene or C.sub.2 -C.sub.12 alkylene which is interrupted by oxygen; ##STR121## or R.sub.15 and R.sub.16 independently of one another are hydrogen, C.sub.1 C.sub.18 alkyl or phenyl, or R.sub.5 and
R.sub.16, together with the C atom to which they are bonded, form a C.sub.5 -C.sub.7 cycloalkylidene ring and
R.sub.17 is C.sub.1 C.sub.8 alkylene or C.sub.2 -C.sub.8 alkylene which is interrupted by oxygen; C.sub.2 -C.sub.8 alkenylene, C.sub.2 -C.sub.8 alkylidene, C.sub.5 C.sub.7 cycloalkylene or phenylene.

### Claim 6 (depends on 1)

A composition according to claim 1, in which
R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently of one another are hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.5 -C.sub.8 cycloalkyl, phenyl, C.sub.7 -C.sub.9 phenylalkyl, hydroxyl, C.sub.1 -C.sub.18 alkoxy, C.sub.1 -C.sub.18 alkanoyloxy, C.sub.3 C.sub.18 alkenoyloxy, benzoyloxy, cyano or --(CH.sub.2).sub.m COR.sub.11, with the condition that at least one of the radicals R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is hydrogen, R.sub.2 is additionally a radical of the formula III and R.sub.4 is additionally a radical of the formula V, and in which at the same time only one radical of the formula III or V occurs in the compound of the formula I ##STR122## R.sub.5, R.sub.6, R.sub.7 and R.sub.8 independendy of one another are hydrogen, chlorine, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.8 cycloalkyl, phenyl, benzyl or cyano, with the condition that at least one of the radicals R.sub.5, R.sub.6, R.sub.7 or R.sub.8 is hydrogen,
R.sub.11 is C.sub.1 C.sub.12 alkoxy,
R.sub.4 is C.sub.1 C.sub.8 alkylene, C.sub.2 C.sub.12 alkylene which is interrupted by oxygen or ##STR123## R.sub.15 and R.sub.16 independendy of one another are hydrogen, C.sub.1 C.sub.8 alkyl or phenyl, or R.sub.15 and R.sub.16, together with the C atom to which they are bonded, form a C.sub.5 C.sub.7 cycloalkylidene ring,
X is oxygen or sulfur,
and m is 0 or 1.

### Claim 7 (depends on 1)

A composition according to claim 1, in which
R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently of one another are hydrogen, C.sub.1 -C.sub.12 alkyl, cyclohexyl, C.sub.7 C.sub.9 phenylalkyl, hydroxyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.12 alkanoyloxy or --(CH.sub.2).sub.m COR.sub.11, with the condition that at least one of the radicals R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is hydrogen,
R.sub.5, R.sub.6, R.sub.7 and R.sub.8 independently of one another are hydrogen, chlorine, C.sub.1 C.sub.8 alkyl or cyclohexyl, with the condition that at least one of the radicals R.sub.5, R.sub.6, R.sub.7 or R.sub.8 is hydrogen,
R.sub.11 is C.sub.1 C.sub.12 alkoxy,
X is oxygen or sulfur, and
m is 0 or 1.

### Claim 8 (depends on 1)

A composition according to claim 1, in which
R.sub.1 is hydrogen, hydroxyl, or C.sub.1 -C.sub.12 alkanoyloxy,
R.sub.2 is hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.7 C.sub.9 phenylalkyl, C.sub.1 -C.sub.3 alkoxy or --(CH.sub.2).sub.m COR.sub.11,
R.sub.3 is hydrogen, hydroxyl or C.sub.1 -C.sub.12 alkanoyloxy,
R.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl or cyclohexyl, with the condition that at least one of the radicals R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is hydrogen,
R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are hydrogen,
R.sub.11 is C.sub.1 -C.sub.12 alkoxy,
X is oxygen or sulfur, and
m is 0 or 1.

### Claim 9 (depends on 1)

A composition according to claim 1, additionally comprising, in addition to components (a) and (b) further additives.

### Claim 10 (depends on 9)

A composition according to claim 9, comprising phenolic antioxidants, light stabilizers and/or processing stabilizers as further additives.

### Claim 11 (depends on 9)

A composition according to claim 9, comprising at least one compound of the organic phosphite or phosphonite type as a further additive.

### Claim 12 (depends on 1)

A composition according to claim 1, comprising natural, semi-synthetic or synthetic polymers as component a).

### Claim 13 (depends on 1)

A composition according to claim 1, comprising thermoplastic polymers, tackifiers or adhesives as component (a).

### Claim 14 (depends on 1)

A composition according to claim 1, comprising a polyolefin as component (a).

### Claim 15 (depends on 1)

A composition according to claim 1, comprising polyethylene or polypropylene as component (a).

### Claim 16 (depends on 1)

A composition according to claim 1, in which component b) is present in an amount of 0.0005 to 5%, based on the weight of component a).