Carboxylic acid esters of hydroxyphenylalkanols as stabilizers
AssigneeCiba-Geigy Corporation
InventorsPaul Dubs, Rita Pitteloud
Life of this patent
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Abstract
The novel compounds of the formula I ##STR1## in which n is an integer from the range from 4 to 8 and m is an integer from the range from 1 to 4, A is the aliphatic, aromatic, araliphatic or heterocyclic radical of a monobasic to tetrabasic carboxylic acid, and R.sup.1 and R.sup.1', independently of one another, are C.sub.1 -C.sub.24 alkyl or C.sub.5 -C.sub.8 cycloalkyl, are suitable for stabilizing organic material against thermal, oxidative or actinic degradation.
Claims18
A compound of the formula I ##STR59## in which n is an integer from the range from 4 to 8 and m is an integer from the range from 1 to 4;
- if m=1, A is C.sub.1 -C.sub.25 alkyl, which is unsubstituted or substituted by C.sub.5 -C.sub.8 cycloalkyl;
- or is C.sub.2 -C.sub.25 alkyl which is interrupted by C.sub.5 -C.sub.8 cycloalkyl or one or more groups selected from --S--, --O-- and --NR.sup.2 --;
- or, if m=1, A is C.sub.5 -C.sub.8 cycloalkyl, which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- C.sub.6 -C.sub.8 cycloalkenyl, which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- phenyl, which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- naphthyl, which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- biphenyl, which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- C.sub.2 -C.sub.25 alkenyl;
- C.sub.6 -C.sub.10 bicycloalkenyl;
- C.sub.7 -C.sub.12 phenylalkyl;
- C.sub.8 -C.sub.12 phenylalkenyl;
- C.sub.11 -C.sub.16 naphthylalkyl;
- C.sub.12 -C.sub.16 naphthylalkenyl;
- C.sub.13 -C.sub.18 biphenylalkyl;
- C.sub.14 -C.sub.18 biphenylalkenyl;
- a group of the formula II ##STR60## if m=2, A is a direct bond;
- C.sub.1 -C.sub.12 alkylene;
- C.sub.2 -C.sub.12 alkenylene;
- C.sub.5 -C.sub.8 cycloalkylene, which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- C.sub.6 -C.sub.8 cycloalkenylene, which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl;
- C.sub.6 -C.sub.10 bicycloalkenylene;
- phenylene;
- naphthylene;
- a divalent heterocyclic radical from the group comprising furan, thiophene or pyrrole, which is saturated on the nitrogen atom by hydrogen or the substituent --R.sup.2 ;
- or, if m=2, A is C.sub.2 -C.sub.36 alkylene which is interrupted by C.sub.5 -C.sub.8 cycloalkylene or phenylene or one or more groups selected from --O-- and --NR.sup.2 --;
- if m=3, A is C.sub.1 -C.sub.8 alkanetriyl;
- C.sub.2 -C.sub.8 alkenetriyl;
- benzenetriyl;
- naphthalenetriyl;
- or C.sub.2 -C.sub.18 alkanetriyl, which is interrupted by at least one of the groups --S--, --O-- or --NR.sup.2 --;
- if m=4, A is a benzene radical, naphthyl radical, tetrahydrofuryl radical or cyclohexyl radical having 4 free valencies;
- R.sup.1 and R.sup.1', independently of one another, are C.sub.1 -C.sub.10 alkyl or C.sub.5 -C.sub.8 cycloalkyl;
- R.sup.2 is H or C.sub.1 -C.sub.4 alkyl;
- R.sup.3 and R.sup.4, independently of one another, are C.sub.1 -C.sub.4 alkyl;
- and with the proviso that, when n is 4, R.sup.1' tert-butyl or cyclohexyl, and R.sup.1 is methyl, tert-butyl or cyclohexyl, and with the further proviso that, when A contains an ethylenic double bond, R.sup.1' is tert-butyl and R.sup.1 is methyl.
A compound of the formula Ia ##STR65## in which n is an integer from the range from 4 to 8 and m is an integer from the range from 1 to 3, if m=1, A is C.sub.1 -C.sub.25 alkyl, which is unsubstituted or substituted by C.sub.5 -C.sub.8 cycloalkyl, or is C.sub.2 -C.sub.25 alkyl, which is interrupted by C.sub.5 -C.sub.8 cycloalkyl or one or more groups selected from --S--, --O-- and --NR.sup.2 --, or, if m=1, A is C.sub.5 -C.sub.8 cycloalkyl, which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl, C.sub.6 -C.sub.8 cycloalkenyl, which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl, phenyl, which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl, naphthyl, which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl, biphenyl, which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl, A is C.sub.2 -C.sub.25 alkenyl, C.sub.6 -C.sub.10 bicycloalkenyl, C.sub.7 -C.sub.12 phenylalkyl, C.sub.8 -C.sub.12 phenylalkenyl, C.sub.11 -C.sub.16 naphthylalkyl, C.sub.12 -C.sub.16 naphthylalkenyl, C.sub.13 -C.sub.18 biphenylalkyl, C.sub.14 -C.sub.18 biphenylalkenyl, or a group of the formula II ##STR66## if m=2, A is a direct bond, C.sub.1 -C.sub.12 alkylene, C.sub.2 -C.sub.12 alkenylene, C.sub.5 -C.sub.8 cycloalkylene, which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl, A is C.sub.6 -C.sub.8 cycloalkenylene, which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl, A is C.sub.6 -C.sub.10 bicycloalkenylene, phenylene, naphthylene or C.sub.2 -C.sub.18 alkylene which is interrupted by C.sub.5 -C.sub.8 cycloalkylene or phenylene or one or more groups selected from --O-- and --NR.sup.2 --,
- if m=3, A is C.sub.1 -C.sub.8 alkanetriyl, C.sub.2 -C.sub.8 alkenetriyl, benzenetriyl, naphthalenetriyl, or C.sub.2 -C.sub.18 alkanetriyl which is interrupted by one or more groups selected from --S--, --O-- and --NR.sup.2 --,
- R.sup.1 is methyl or tert-butyl,
- R.sup.2 is H or C.sub.1 -C.sub.4 alkyl,
- R.sup.3 and R.sup.4, independently of one another, are C.sub.1 -C.sub.4 alkyl, and with the proviso that, when n is 4, R.sup.1 methyl, tert-butyl or cyclohexyl, and with the further proviso that, when m is 1 or 2 and A is alkenyl or phenylalkenyl or alkenylene, R.sup.1 is methyl.
A composition containing an organic material sensitive to thermal, oxidative or/and actinic degradation and an effective stabilising amount of a compound of the formula IV ##STR67## in which n is an integer from the range from 4 to 8 and R.sup.1 is method and R.sup.1' is tert-butyl
Dependencies are inferred from the claim text.