2-(2′-hydroxyphenyl)benzotriazoles used as U.V....

Details 2-(2′-hydroxyphenyl)benzotriazoles used as U.V.... 2-(2′-hydroxyphenyl)benzotriazoles used as U.V....

2000-04-27

2002-06-18

Morris, Patricia L. (Department: 1625)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S261000

Reexamination Certificate

active

06407254

ABSTRACT:

The present invention relates to 2-(2′-hydroxyphenyl)benzatriazoles.
More specifically, the present invention relates to 2-(2′-hydoxyphenyl)benzotraizoles 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.
For Example, EP-A-0 057 160 discloses 2-(2′-hydroxyphenyl-3′-tert.-butyl)benzotriazoles comprising a hydrocarbon chain which contains a carbonyl group and their use as UV stabilizers.
U.S. Pat. No. 4,077,971 discloses tetrahydrophthalimide methyl-2-phenylbenzatriazoles useful as ultraviolet absorbers. U.S. Pat. No. 3,629,192, CH Patent No. 476 745 and FR Patent 1 324 899 disclose 2-(2′-hydroxyphenyl-)benzotriazoles comprising amine or amide groups. The compounds are said to act as light-stabilizers.
U.S. Pat. Nos. 4,069,197 and 4,044,019 disclose substituted hydantoins and their use as stabilizers for synthetic organic polymeric materials.
The benzotriazoles however have various disadvantages. In fact, they are often rather volatile, they have a low thermal stability and, as they sometimes have a significant 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 (I):
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
alkynyl group; a C
5
-C
18
cycloalkyl group, said cycloalkyl group optionally substituted; a C
7
-C
15
arylalkyl or alkylaryl group; a C
6
-C
14
aryl group, said aryl group optionally 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 optionally 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
alkynyl group; a C
5
-C
18
cycloalkyl group, said cycloalkyl group optionally substituted; a C
7
-C
15
arylalkyl or alkylaryl group; a C
6
-C
14
aryl group, said aryl group optionally substituted; a heterocyclic group with 5 or 6 atoms containing at least one heteroatom selected from oxygen, nitrogen and sulfur, said heterocyclic group optionally 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
alkynyl group; a C
5
-C
18
cycloalkyl group, said cycloalkyl group optionally substituted; a C
7
-C
15
arylalkyl or alkylaryl group; a C
6
-C
14
aryl group, said aryl group optionally substituted; a linear or branched C
1
-C
18
alkoxy group; a heterocyclic group with 5 or 6 atoms containing at least one heteroatom selected from oxygen, nitrogen and sulfur, said heterocyclic group optionally 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
alkynyl group; a C
5
-C
18
cycloalkyl group, said cycloalkyl group optionally substituted; a C
7
-C
15
arylalkyl or alkylaryl group; a C
6
-C
14
aryl group, said aryl group optionally substituted; a heterocyclic group with 5 or 6 atoms containing at least one heteroatom selected from oxygen, nitrogen and sulfur, said heterocyclic group optionally 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 optionally 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 optionally 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
alkynyl 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
1
-C
18
alkenyl groups are: vinyl, propylene, butylene, pentylene, hexylene, etc.
Examples of C
2
-C
18
alkynyl groups are: acetylene, propyne, butyne, 2-butyne, etc.
Examples of C
5
-C
18
cycloalkyl groups, optionally 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, optionally 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, optionally substituted, are: piperidine, morpholine, piperazine, triazole, tetramethylpiperidine, pentamethylpiperidine, tetramethylmorpholine, pentamethylmorpholine, 4-hydroxy-tetramethylpiperidine, etc.
Specific examples of compounds having general formula (I) 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) comprises:
(a) reacting a 2-(2′hydroxyphenyl)benzotriazole having general formula (IX):
 wherein X and R have the same meanings defined above, with a secondary amine having general formula (X):
wherein R
7
and R
8
, the same or different, preferably the same, represent a linear alkyl group having from 3 or more carbon atoms, in the presence of formaldehyde or para-formaldehyde, preferably para-formaldehyde and an inert organic solvent such as, for example, an alcohol, preferably n-butanol, at a temperature ranging from 95° C. to 100° C., for a time ranging from 40 hours to 60 hours, obt

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