Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-08-16
2003-05-13
Shah, Mukund J. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S724000, C544S171000, C544S173000, C544S175000, C562S575000, C562S553000
Reexamination Certificate
active
06562815
ABSTRACT:
The invention relates to new 3,3,5,5-tetrasubstituted 2-morpholinones, their use as stabilizers for organic material against deleterious effects of light, oxygen and/or heat, organic material correspondingly stabilized and a process for stabilizing organic material.
Structure and numbering of 2-morpholinone is as shown in the formula:
An important type of stabilizers-for organic material are the hindered amine light stabilizers, whose chemical structure is usually derived from 2,2,6,6-tetramethylpiperidine.
The use of some 3,3-disubstituted 2-morpholinones as an additive for fuels or lubricants is described in U.S. Pat. No. 3,371,040.
U.S. Pat. Nos. 4,528,370, 4,914,232 and 5,089,614 disclose as a new class of light stabilizers for organic materials some specific 3,3,5,5-tetrasubstituted 2-morpholinones. Some of these compounds are also described by J. T. Lai in Synthesis (1984), 122.
EP-A-248494 describes the formation of a polybutadiene capped by reaction with 3,3,5,5-tetramethy-morpholin-2-one.
It has now been found that a modified class of compounds of the 2-morpholinone type is especially well suitable for protecting organic material against harmful effects of light, oxygen and/or heat.
Object of the invention is therefore a compound of the formula F
(A′—Z)
m
—X (F),
wherein
m is a number from 1 to 8;
Z is a direct bond, —O—, —S—, —SO—, —SO
2
— or —NR′
14
—;
X is an organic anchor group of valency m comprising 1-300 carbon and 0-60 hetero atoms; and in case that m is not 1, X may also be a direct bond, SO
2
, P or PO;
A′ is a monovalent group of the formula E
containing one linking group;
G
1
is hydrogen; C
1
-C
18
alkyl; C
2
-C
18
alkyl substituted by OH and/or phenyl; oxyl; OH; C
2
-C
12
cyanoalkyl; C
2
-C
12
cyanoalkoxy; C
1
-C
18
alkoxy; C
5
-C
12
cycloalkoxy; C
3
-C
8
alkenyl; C
3
-C
8
alkynyl; C
3
-C
8
alkenyloxy; C
7
-C
12
phenylalkyl; C
7
-C
12
phenylalkyl substituted by hydroxy, C
1
-C
4
alkyl and/or C
1
-C
4
alkoxy; C
7
-C
15
phenylalkoxy; C
7
-C
15
phenylalkoxy, which is substituted by C
1
-C
4
alkyl and/or C
1
-C
4
alkoxy; or G
1
is C
1
-C
8
alkanoyl; C
3
-C
5
alkenoyl; C
1
-C
18
alkanoyloxy; C
3
-C
8
epoxyalkyl;
or G
1
is the linking group —R
10
—;
G
2
and G
4
are, independently of one another, C
1
-C
18
alkyl, C
3
-C
8
alkenyl, C
5
-C
12
cycloalkenyl, C
5
-C
12
cycloalkyl, or an oligocydic hydrocarbon residue of 6-12 carbon atoms;
G
3
is as defined for G
2
or is C
1
-C
8
hydroxyalkyl; or G
2
and G
3
together are (CH
2
)
e
, where e is a number from 4 to 11;
or G
3
is the linking group —R
5
—;
G
5
is as defined for G
4
or is C
1
-C
8
hydroxyalkyl; or G
4
and G
5
together are (CH
2
)
e
, where e is a number from 4 to 11;
or G
5
is the linking group —R
5
—;
G
6
is as defined for G
4
or is hydrogen;
or G
6
is the linking group, which is a direct bond or —R
5
—;
R
5
is C
1
-C
8
alkylene; C
1
-C
8
alkylene-CO—; or C
1
-C
8
alkylene substituted by OH or OCOR
15
;
R
10
is C
1
-C
8
alkylene or —CO— or C
1
-C
8
alkylene-CO—;
R′
10
is hydrogen or C
1
-C
8
alkyl or C
5
-C
12
cycloalkyl;
R′
14
is hydrogen, C
1
-C
18
alkyl; C
5
-C
12
cycloalkyl; C
3
-C
18
alkyl interrupted by O or NR′
10
;
C
5
-C
12
cycloalkyl, which is substituted by C
1
-C
4
alkyl; C
2
-C
17
alkenyl; C
7
-C
15
phenylalkyl; C
7
-C
15
phenylalkyl, which is substituted by C
1
-C
4
alkyl, C
1
-C
4
alkoxy;
R
15
is hydrogen; C
1
-C
17
alkyl; C
3
-C
50
alkyl interrupted by O; C
5
-C
12
cycloalkyl; C
5
-C
12
cycloalkyl, which is substituted by C
1
-C
4
alkyl; C
2
-C
17
alkenyl; phenyl; phenyl which is substituted by C
1
-C
4
alkyl, C
1
-C
4
alkoxy and/or hydroxy; C
7
-C
15
phenylalkyl; C
7
-C
15
phenylalkyl, which is substituted by C
1
-C
4
alkyl, C
1
-C
4
alkoxy and/or hydroxy; or is C
8
-C
12
phenylalkenyl;
provided that Z is —O—, —S—, —SO—, —SO
2
— or —NR′
14
— if m is 1 and the linking group in formula E is G
3
or G
5
.
All residues may be straight chain or branched unless otherwise indicated.
An oligocyclic hydrocarbon residue of 6-12 carbon atoms is mainly bicycloalkyl, bicydoalkenyl, tricycloalkyl or tricycloalkenyl of 6-12 carbon atoms.
A substituent halogen is —F, —Cl, —Br or —I; preferably —F or —Cl, especially —Cl.
Alkali metal is mainly Li, Na, K, Rb, Cs, especially Na or K; it is often present as cation forming a salt of a carboxy group.
Open bonds in alkylene or cycloalkylene residues may be attached on different carbon atoms or on the same carbon atom, thus embracing alkylidene or cycloalkylidene. Alkylidene and cycloalkylidene are saturated divalent hydrocarbons having both open bonds localized on the same carbon atom; for instance, C
1
-C
4
alkylidene embraces C
1
alkylidene which is methylene.
Organic residues like X as an organic anchor group are hydrocarbons which may additionally contain hetero atoms as specified. A hydrocarbon alone, i.e. without hetero atoms, consists of carbon and hydrogen; if there is more than one carbon atom present, these can be linked to each other by single, double or triple bonds, open bonds being linked to hydrogen as known in organic chemistry.
Of pronounced value are compounds of the formula F wherein m is 1 and X contains at least 5 carbon or hetero atoms, especially 5 carbon atoms, or wherein m is a number from the range 2-8.
Preferably, X is an m-valent hydrocarbon radical consisting of 1-100 carbon atoms, or is an m-valent organic radical consisting of 1-200 carbon atoms and 1-60 hetero atoms selected from N, O, S, halogen, P, Si, alkali metal, Ca and Zn, and hydrogen atoms, or X is P.
Usually, m is the number of groups of the 2-morpholinone type in compounds of the formula F, and X does not comprise a group of the 2-morpholinone type.
Hetero atoms are non-carbon and non-hydrogen atoms, for instance N, O, S, halogen, P, Si; alkali metal, Ca or Zn can be contained e.g. as carboxylate. Preferred hetero atoms are N, O, S or P, especially N, S and O.
Organic residues or hydrocarbons containing heteroatoms, such as alkyl or alkylene interrupted. by hetero groups like oxygen or NH, usually contain these heteroatoms as typical functional groups like oxo, oxa, hydroxy, carboxy, ester, amino, amido, nitro, nitrilo, isocyanato, fluoro, chloro, bromo, phosphate, phosphonate, phosphite, silyl, thio, sulfide, sulfinyl, sulfo, heterocyclyl including pyrrolyl, indyl, carbazolyl, furyl, benzofuryl, thiophenyl, benzothiophenyl, pyridyl, chinolyl, isochinolyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazolyl, benzotriazolyl, triazinyl, pyrazolyl, imidazolyl, thiazoly, oxazolyl, and corresponding saturated and/or substituted groups like, for example, piperidyl, piperazinyl, morpholinyl etc. They may be interrupted by one or more of these groups; usually there are no linkages of the type O—O, O—N (except nitro, cyanato, isocyanato, nitroso), N—N (except in heterocyclic ring structures), N—P or P—P present, regardless of the order.
Preferably, in organic residues or hydrocarbons containing heteroatoms, for example alkyl or alkylene residues like X, R
5
or R
10
, there is not more than one heteroatom attached by a single bond to the same carbon atom. A spacer consisting of one or more heteroatoms such as defined below usually is embedded in a carbon chain or ring or inserted into a carbon-hydrogen bond.
Preferred compounds are those wherein R
5
is C
1
-C
4
alkylene, especially methylene, and R
10
is —CH
2
—CH(R′)— with R′ being H or C
1
-C
4
alkyl and Z is O.
Z is preferably a direct bond, —O— or —NR′
14
—; especially —O— or —NR′
14
—.
When Z in formula F is a direct bond, X directly bonds to A; when a linking group in formula E is a direct bond, the morpholinone ring directly bonds to Z or, if Z is also a direct bond, to X. In case that both Z and X are direct bonds, 2 moieties of the formula E are directly linked together.
Also preferred are compounds of formula F, wherein G
1
is the linking group —CH
2
—CH(R′)— with R′ being H or C
1
-C
4
alkyl and Z is as defined, or G
5
is the linking group C
1
-C
4
alkylene,
Of particular interest are compounds of t
Bolle Thomas
Laver Hugh Stephen
Lazzari Dario
Rossi Mirko
Ciba Specialty Chemicals Corporation
Patel Sudhaker B.
Shah Mukund J.
Stevenson Tyler A.
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