2-(2′Hydroxyphenyl) benzotriazoles and process for...

Details 2-(2′Hydroxyphenyl) benzotriazoles and process for... 2-(2′Hydroxyphenyl) benzotriazoles and process for...

2000-06-06

2001-07-31

Aulakh, Charahjit S. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C524S091000, C252S403000

Reexamination Certificate

active

06268505

ABSTRACT:

The present invention relates to 2-(2′-hydroxyphenyl)benzotriazoles.
More specifically, the present invention relates to 2-(2′-hydroxyphenyl)benzotriazoles containing a 2,4-imidazolidinedione group or a 2,4-imidazolidinedione-5,5-disubstituted group in the molecule, a process for their preparation and their use as light stabilizers for organic polymers.
The present invention also relates to the polymeric compositions stabilized with the above benzotriazoles and to the end-products obtained from these compositions.
2-(2′-hydroxyphenyl)benzotriazoles which can be used as light stabilizers are known in the art. These benzotriazoles however have various disadvantages. In fact, they are often rather volatile, they have a low thermal stability and, as they sometimes have an absorption at 400 nm, they give the polymers into which they are incorporated, a yellow colouring.
The Applicant has now surprisingly found that 2-(2′-hydroxyphenyl)benzotriazoles containing a 2,4-imidazolidinedione group or a 2,4-imidazolidinedione-5,5-disubstituted group in the molecule, are capable of overcoming the drawbacks of the known art. In fact, the above benzotriazoles have a low volatility (they are therefore able to remain inside the stabilized organic polymer for a longer period) and also a high thermal stability. In addition, they have a low absorption at &lgr;=400 nm and maintain the absorption at the two &lgr; typical of benzotriazoles, at about 300 nm and 340 nm and consequently they do not give a yellow colouring to the polymers into which they are incorporated.
The present invention therefore relates to 2-(2′-hydroxyphenyl)benzotriazoles having general formula
wherein:
X represents a hydrogen atom; a halogen atom selected from chlorine and bromine; a linear or branched C
1
-C
18
alkyl group; a linear or branched C
1
-C
18
alkoxyl group; a cyano group;
R represents a halogen atom selected from chlorine and bromine; a linear or branched C
1
-C
18
alkyl group; a linear or branched C
2
-C
18
alkenyl group; a linear or branched C
2
-C
18
alkinyl group; a C
5
-C
18
cycloalkyl group, said cycloalkyl group possibly substituted; a C
7
-C
15
arylalkyl or alkylaryl group; a C
6
-C
14
aryl group, said aryl group possibly substituted; a linear or branched C
1
-C
18
alkoxyl group; a heterocyclic group with 5 or 6 atoms containing at least one heteroatom selected from oxygen, nitrogen and sulfur, said heterocyclic group possibly substituted; a group having the formula:
a —COR
4
group or a —NR
5
R
6
group wherein R
4
, R
5
and R
6
, the same or different, represent a linear or branched C
1
-C
18
alkyl group; a linear or branched C
2
-C
18
alkenyl group; a linear or branched C
2
-C
18
alkinyl group; a C
5
-C
18
cycloalkyl group, said cycloalkyl group possibly substituted; a C
7
-C
15
arylalkyl or alkylaryl group; a C
6
-C
14
aryl group, said aryl group possibly substituted; a heterocyclic group with 5 or 6 atoms containing at least one heteroatom selected from oxygen, nitrogen and sulfur, said heterocyclic group possibly substituted;
or R represents an ester group having general formula (II), (III) or (IV):
or an amide group having general formula (V):
 wherein R′ represents a linear or branched C
1
-C
18
alkyl group; a linear or branched C
2
-C
18
alkenyl group; a linear or branched C
2
-C
18
alkinyl group; a C
5
-C
18
cycloalkyl group, said cycloalkyl group possibly substituted; a C
7
-C
15
arylalkyl or alkylaryl group; a C
6
-C
14
aryl group, said aryl group possibly substituted; a linear or branched C
1
-C
18
alkoxyl group; a heterocyclic group with 5 or 6 atoms containing at least one heteroatom selected from oxygen, nitrogen and sulfur, said heterocyclic group possibly substituted; or R represents a 4,4′-ethylidenebisphenol group having formula (VI):
R
1
represents a hydrogen atom; a linear or branched C
1
-C
18
alkyl group; a linear or branched C
2
-C
18
alkenyl group; a linear or branched C
2
-C
18
alkinyl group; a C
5
-C
18
cycloalkyl group, said cycloalkyl group possibly substituted; a C
7
-C
15
arylalkyl or alkylaryl group; a C
6
-C
14
aryl group, said aryl group possibly substituted; a heterocyclic group with 5 or 6 atoms containing at least one heteroatom selected from oxygen, nitrogen and sulfur, said heterocyclic group possibly substituted; an acyl group having general formula (VII):
or an ester group having general formula (VIII):
 wherein R′ has the same meanings described above;
R
2
and R
3
, the same or different, represent a hydrogen atom; a linear or branched C
1
-C
18
alkyl group; a phenyl group; a heterocyclic group with 5 or 6 atoms containing at least one heteroatom selected from oxygen, nitrogen and sulfur, said heterocyclic group possibly substituted.
The compounds having general formula (I) can be used as light stabilizers for organic polymers.
When the C
5
-C
18
cycloalkyl groups, the C
6
-C
14
aryl groups and the heterocyclic groups with 5 or 6 atoms are defined as being possibly substituted, these groups are substituted with: halogen atoms selected from chlorine and bromine, linear or branched C
1
-C
18
alkyl groups, linear or branched C
2
-C
18
alkenyl groups; linear or branched C
2
-C
18
alkinyl groups, OH groups, NH groups, SH groups.
Examples of C
1
-C
18
alkyl groups are: methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, t-butyl, t-amyl, 2-ethylhexyl, n-octyl, 1,1,3,3-tetramethylbutyl,-n-dodecyl, 1,1,7,7-tetramethyloctyl, n-octadecyl, etc.
Examples of C
2
-C
18
alkenyl groups are: vinyl, propylene, butylene, pentylene, hexylene, etc.
Examples of C
2
-C
18
alkinyl groups are: acetylene, propine, butine, 2-butine, etc.
Examples of C
5
-C
18
cycloalkyl groups, possibly substituted, are: cyclohexyl, cyclopentyl, methylcyclohexyl, etc.
Examples of C
7
-C
15
arylalkyl or alkylaryl groups are: benzyl, 2-phenylethyl, 4-t-butylbenzyl, etc.
Examples of C
6
-C
14
aryl groups, possibly substituted, are: phenyl, naphthyl, anthracenyl, 2-hydroxyphenyl, etc.
Examples of C
1
-C
18
alkoxyl groups are: methoxyl, ethoxyl, propoxyl, n-butoxyl, etc.
Examples of heterocyclic groups with 5 or 6 atoms, possibly substituted, are: piperidine, morpholine, piperazine, triazole, tetramethylpiperidine, pentamethylpiperidine, tetramethylmorpholine, pentamethylmorpholine, 4-hydroxy-tetramethylpiperidine, etc.
Specific examples of compounds having general formula (I), which in no way limit the scope of the present invention, are:
The compounds having general formula (I) of the present invention can be prepared with various processes.
A further object of the present invention relates to a process for the preparation of 2-(2′-hydroxyphenyl)benzotriazoles having general formula (I).
A process for the preparation of compounds having general formula (I) consists in reacting a 2-(2′hydroxyphenyl)benzotriazole having general formula (IX):
wherein X and R have the same meanings defined above, with a 2,4-imidazolidinedione-1,3-dimethylol having general formula (X) or with a 2,4-imidazolidinedione-1-methylol having general formula (Xa), preferably with a 2,4-imidazolidinedione-1-methylol having general formula (Xa):
wherein R
2
and R
3
have the same meanings described above, in the presence of concentrated sulfuric acid, for example, at a concentration ranging from 80% to 96%, at a temperature ranging from −5° C. to +80° C. The desired compound is isolated from the mixture thus obtained operating according to processes known in the art such as, for example, by diluting with water, preferably with a water-ice mixture and removing the solid obtained by filtration followed by washing and crystallization in the presence of inert organic solvents.
Inert organic solvents which can be used for the above crystallization are: linear or cyclic aliphatic hydrocarbons such as, for example, hexane, heptane, cyclohexane, methylcyclohexane, etc.; aromatic hydrocarbons such as, for example, toluene, etc.; alcohols such as, for example, methanol, isopropanol, etc.; chlorinated aromatic

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