Use of isoindolinone derivatives as stabilizers for organic...

Details Use of isoindolinone derivatives as stabilizers for organic... Use of isoindolinone derivatives as stabilizers for organic...

1998-12-09

2001-04-03

Dees, Jose′ G. (Department: 1616)

Drug, bio-affecting and body treating compositions

Topical sun or radiation screening, or tanning preparations

C424S060000, C424S070900, C424S401000, C514S844000, C514S970000, C514S972000

Reexamination Certificate

active

06210657

ABSTRACT:

The invention relates to the use of isoindolinone derivatives as stabilizers for organic materials.
As is known, organic material, in particular plastics and surface coatings, is destroyed very rapidly, especially by the effect of light. This destruction usually becomes apparent by the material yellowing, discoloring, cracking or becoming brittle. The stabilizers and light protection agents used to date have been unable to achieve satisfactory protection against the destruction of organic material by light, oxygen and heat.
Thus, for example, EP-A-057 160 recommends o-hydroxyphenylbenzotriazole derivatives of the formula
in which A is, for example, polyethyleneoxycarbonylalkyl radicals or polyethyleneoxycarbonylalkylene bridge members connecting two o-hydroxyphenylbenzotriazole systems, as UV absorbers for plastics and surface coatings. Although said o-hydroxyphenylbenzotriazole derivatives have the desired spectroscopic properties (strong absorption bands in the range from 280 to 360 nm), they do not satisfy today's requirements as regards their stabilization and light protection action.
It is an object of the present invention to provide stabilizers and light protection agents which effectively protect organic material.
We have found that this object is achieved according to the invention by the use of isoindolinone derivatives of the formula I,
in which the variables independently of one another have the following meanings:
R
1
is hydrogen, COOR
4
, COR
4
, CONR
4
R
5
, CN, C
1
-C
20
-alkyl, C
2
-C
10
-alkenyl, C
3
-C
10
-cycloalkyl, C
3
-C
10
-cycloalkenyl, aryl or heteroaryl, substituted or unsubstituted;
R
2
is COOR
4
, COR
4
, CONR
4
R
5
or CN;
R
1
and R
2
together are C
7
-C
10
-bicycloalkyl or C
7
-C
10
-bicycloalkenyl;
R
3
is hydrogen, C
1
-C
20
-alkyl, C
2
-C
10
-alkenyl, C
3
-C
10
-cycloalkyl, C
3
-C
10
-cycloalkenyl, C
1
-C
12
-alkoxy, C
1
-C
20
-alkoxycarbonyl, C
1
-C
12
-alkylamino, C
1
-C
12
-dialkylamino, aryl or heteroaryl, substituted or unsubstituted, substituents which confer solubility in water, selected from the group consisting of carboxylate, sulfonate or alkylammonium radicals;
R
4
and R
5
independently of one another are hydrogen, C
1
-C
20
-alkyl, C
2
-C
10
-alkenyl, C
3
-C
10
-cycloalkyl, C
3
-C
10
-cycloalkenyl; aryl or heteroaryl, substituted or unsubstituted;
as stabilizers for organic materials.
Alkyl radicals R
1
and R
3
to R
5
which may be mentioned are branched or unbranched C
1
-C
20
-alkyl chains, preferably methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl,
1
,
1
-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,
1,1-dimetliylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, n-heptyl, 2-ethylhexyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl or n-eicosyl.
Alkenyl radicals R
1
and R
3
to R
5
which may be mentioned are branched or unbranched C
2
-C
10
-alkenyl chains, preferably vinyl, propenyl, isopropenyl, 1-butenyl, 2-butenyl, 1-pentenyl, 2-pentenyl, 2-methyl-1-butenyl, 2-methyl-2-butenyl, 3-methyl-1-butenyl, 1-hexenyl, 2-hexenyl, 1-heptenyl, 2-heptenyl, 1-octenyl or 2-octenyl.
Cycloalkyl radicals R
1
and R
3
to R
5
which may be mentioned are, preferably, branched or unbranched C
3
-C
10
-cycloalkyl radicals, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclopropyl, 1-ethylcyclopropyl, 1-propylcyclopropyl, 1-butylcyclopropyl, 1-pentylcyclopropyl, 1-methyl-1-butylcyclopropyl, 1,2-dimethylcyclopropyl, 1-methyl-2-ethylcyclopropyl, cyclooctyl, cyclononyl or cyclodecyl.
Cycloalkenyl radicals R
1
and R
3
to R
5
which may be mentioned are, preferably, branched or unbranched C
3
-C
10
-cycloalkenyl radicals having one or more double bonds, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, 1,3-cyclohexadienyl, 1,4-cyclohexadienyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, 1,5-cyclooctadienyl, cyclooctatetraenyl, cyclononenyl or cyclodecenyl.
The cycloalkenyl and cycloalkyl radicals may be unsubstituted or substituted by one or more, e.g. one to three, radicals, such as halogen, e.g. fluorine, chlorine or bromine, cyano, nitro, amino, C
1
-C
4
-alkylamino, C
1
-C
4
-dialkylamino, hydroxyl, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy or other radicals, or may contain from 1 to 3 heteroatoms, such as sulfur or nitrogen, whose free valences may be saturated by hydrogen or C
1
-C
4
-alkyl, or oxygen in the ring.
Bicycloalkyl or bicycloalkenyl radicals, which may be formed by R
1
and R
2
together, which may be mentioned are saturated or unsaturated C
7
-C
10
bicyclic ring systems, in particular bicyclic terpenes; such as pinane, pinene, bornane, camphor derivatives or also adamantine.
Suitable alkoxy radicals R
3
are those containing from 1 to 12 carbon atoms, preferably from 1 to 8 carbon atoms.
The following are given by way of example:
methoxy
ethoxy
iso-propoxy
n-propoxy
1-methylpropoxy
n-butoxy
n-pentoxy
2-methylpropoxy
3-methylbutoxy
1,1-dimethylpropoxy
2,2-dimethylpropoxy
hexoxy
1-methyl-1-ethylpropoxy
heptoxy
octoxy
2-ethylhexoxy
Alkoxycarbonyl radicals R
3
are, for example, esters which contain the abovementioned alkoxy radicals or radicals of higher alcohols, for example, containing up to 20 carbon atoms, such as iso-C
15
-alcohol.
Suitable mono- or dialkylamino radicals R
3
are those which contain alkyl radicals having from 1 to 12 carbon atoms, for example methyl, n-propyl, n-butyl, 2-methylpropyl, 1,1-dimethylpropyl, hexyl, heptyl, 2-ethylhexyl, isopropyl, 1-methylpropyl, n-pentyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-methyl-1-ethylpropyl and octyl.
Aryl is taken to mean aromatic rings or ring systems having from 6 to 18 carbon atoms in the ring system, for example phenyl or naphthyl, which may be unsubstituted or substituted by one or more radicals such as halogen, for example fluorine, chlorine or bromine, cyano, nitro, amino, C
1
-C
4
-alkylamino, C
1
-C
4
-dialkylamino, hydroxyl, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy or other radicals. Preference is given to unsubstituted or substituted phenyl, methoxyphenyl and naphthyl.
Heteroaryl radicals are advantageously simple or fused aromatic ring systems having one or more heteroaromatic 3- to 7-membered rings. The heteroatoms present in the ring or ring system may be one or more nitrogen, sulfur and/or oxygen atoms.
Examples of hydrophilic radicals, i.e. radicals imparting water solubility to the compounds of the formula I, R
3
are carboxyl and sulfoxy radicals and, in particular, salts thereof with any desired physiologically compatible cations, such as the alkali metal salts or the trialkylammonium salts, such as tri-(hydroxyalkyl) ammonium salts or the 2-methylpropan-1-ole-2-ammonium salts. Alkylammonium radicals containing any desired physiologically compatible anion are also suitable.
Preference is given to those compounds of the formula I in which the variables independently of one another have the following meanings:
R
1
and R
2
are COOR
4
, COR
4
, CONR
4
R
5
or CN;
R
3
is hydrogen, C
1
-C
8
-alkyl, C
1
-C
8
-alkoxy, C
1
-C
20
-alkoxycarbonyl, C
1
-C
12
-alkylamino, C
1
-C
12
-dialkylamino, aryl or heteroaryl, substituted or unsubstituted, substituents which confer solubility in water, selected from the group consisting of carboxylate, sulfonate or alkylammonium radicals;
R
4
and R
5
are hydrogen, C
1
-C
8
-alkyl, C
5
-C
6
-cycloalkyl or phenyl.
Particular preference is given to those compounds of the formula I in which the variables independently of one another have the following meanings:
R
1
and R
2
are COOR
4
, COR
4
, CONR
4
R
5
or CN;
R
3
is hydrogen, C
1
-C
8
-alkyl, C
1
-C
8
-alkoxy, C
1
-C
20
-alkoxycarbonyl, C

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