Heteroaryl substituted hydroxyphenyltriazine uv-absorbers

Details Heteroaryl substituted hydroxyphenyltriazine uv-absorbers Heteroaryl substituted hydroxyphenyltriazine uv-absorbers

2003-03-31

2004-12-28

Balasubramanian, Venkataraman (Department: 1624)

Compositions

Preservative agents

Anti-oxidants or chemical change inhibitants

C424S401000, C524S091000, C524S100000, C544S215000

Reexamination Certificate

active

06835329

ABSTRACT:

The present invention relates to new compounds and, in particular, to new heterocyclic substituted hydroxyphenyltriazine compounds having excellent absorption spectrum characteristics, good resistance to exposure to UV light and excellent thermal stability, and to the use of the new compounds as UV absorbers.
If it is desired to increase the light stability of an organic material, especially a coating, a light stabilizer is usually added. A class of light stabilizers which is very frequently employed comprises the UV absorbers, which protect the material by absorbing the harmful radiation via chromophores. An important group of UV absorbers is the triphenyltriazines, which are described, e.g., in EP-A-434 608, EP-A-520 938, U.S. Pat. No. 4,619,956, EP-A-483 488, EP-A-500 496, EP-A-502 816 and EP-A-506 615.
A new group of hydroxyphenyltriazine compounds has now been found which have improved absorption spectrum characteristics, superior resistance to exposure to UV light and excellent thermal stability, relative to known triphenyltriazine compounds.
According to the present invention, there are provided compounds having the formula:
in which each of the radicals
R
1
, R
2
, R
3
and R
4
, independently, represent hydrogen, hydroxy, halogen, C
1
-C
20
-alkyl, C
1
-C
20
-alkoxy, CN or COOR
5
, in which R
5
is C
1
-C
20
-alkyl and
Z represents a heterocyclic residue selected from the 2H-benzo[1,2-d]triazol-2-yl, 2H-naphtho[1,2-d]triazol-2-yl, benzimidazol-2-yl, benzoxazol-2-yl and benzofuran-2-yl moieties, optionally substituted by C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, halogen or NHCOC
1
-C
4
-alkyl.
Preferred compounds according to the invention are those having the formula (1) in which R
1
and R
3
each, independently represent hydrogen, hydroxy, halogen, C
1
-C
10
-alkyl, C
1
-C
10
-alkoxy, CN or COOR
5
, in which R
5
is C
1
-C
4
-alkyl and R
2
and R
4
are hydrogen, compounds in which R
1
represents hydrogen, hydroxy, chlorine, C
1
-C
10
-alkyl or C
1
-C
10
-alkoxy and R
3
is hydrogen being especially preferable.
Furthermore, within the scope of the compounds of formula (1), those in which Z is a 2H-benzo[1,2-d]triazol-2-yl or a 2H-naphtho[1,2-d]triazol-2-yl residue which is unsubstituted or substituted by C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, halogen or NHCOC
1
-C
4
-alkyl and those in which Z is a benzimidazol-2-yl, benzoxazol-2-yl or a benzofuran-2-yl residue which is unsubstituted or substituted by C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, halogen or NHCOC
1
-C
4
-alkyl are of particular interest.
Particularly preferred compounds are those in which, in formula (1), R
1
represents hydrogen, hydroxy or C
1
-C
10
-alkoxy, R
2
, R
3
and R
4
are hydrogen and Z represents a 2H-benzo[1,2-d]triazol-2-yl or a 2H-naphtho[1,2-d]triazol-2-yl residue which is unsubstituted or substituted by NHCOCH
3
.
When R
1
, R
2
, R
3
and/or R
4
is halogen, such halogen substituents are fluorine, bromine, iodine or, especially, chlorine substituents.
C
1
-C
20
alkyl groups R
1
, R
2
, R
3
R
4
and/or R
5
may be branched or unbranched such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, 1,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3methylheptyl, n-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, n-nonyl, n-decyl, n-undecyl, 1-methylundecyl, n-dodecyl, 1,1,3,3,5,5-hexamethylhexyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl and n-eicosyl.
C
1
-C
20
alkoxy groups R
1
, R
2
, R
3
and/or R
4
may be branched or unbranched such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, t-butoxy, 2-ethylbutoxy, n-pentoxy, isopentoxy, 1-methylpentoxy, 1,3-dimethylbutoxy, n-hexoxy, 1-methylhexoxy, n-heptoxy, isoheptoxy, 1,1,3,3-tetramethylbutoxy, 1-methylheptoxy, 3-methylheptoxy, n-octoxy, 2-ethylhexoxy, 1,1,3-trimethylhexoxy, 1,1,3,3-tetramethylpentoxy, n-nonoxy, n-decoxy, n-undecoxy, 1-methylundecoxy, n-dodecoxy, 1,1,3,3,5,5-hexamethylhexoxy, n-tridecoxy, n-tetradecoxy, n-pentadecoxy, n-hexadecoxy, n-heptadecoxy, n-octadecoxy and n-eicosoxy groups.
The new compounds of formula (1) may be prepared by reacting an acid chloride of the formula
with a salicylamide derivative to yield a benzoxazinone derivative of the formula
and, subsequently, reacting the compound of formula (3) with a benzamidine hydrochloride of the formula
whereby R
1
, R
2
, R
3
, R
4
and Z are as previously defined.
The benzoxazinone compounds of formula (3) are new.
Consequently, a further aspect of the invention is a benzoxazinone compound of formula (3) in which R
1
and R
2
, independently, represent hydrogen, hydroxy, halogen, C
1
-C
20
-alkyl, C
1
-C
20
-alkoxy, CN or COOR
5
, in which R
5
is C
1
-C
20
-alkyl and Z represents a heterocyclic residue selected from the 2H-benzo[1,2-d]triazol-2-yl, 2H-naphtho[1,2-d]triazol-2-yl, benzimidazol-2-yl, benzoxazol-2-yl and benzofuran-2-yl moieties, optionally substituted by C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, halogen or NHCOC
1
-C
4
-alkyl.
Preferred compounds of formula (3) are those in which R
1
represents hydrogen, hydroxy or C
1
-C
10
-alkoxy, R
2
is hydrogen and Z represents a 2H-benzo[1,2-d]triazol-2-yl or a 2H-naphtho[1,2-d]triazol-2-yl residue which is unsubstituted or substituted by NHCOCH
3
.
The novel triazine compounds are very good UV absorbers and are therefore useful as stabilizers for organic polymers, especially coating materials, against damage thereto by light and as light stabilizers for textile fibre materials.
Particular advantages of the novel compounds include their surprisingly high absorption in the 300 to 400 nm region of the electromagnetic spectrum. Material stabilized with the compounds according to the invention features outstanding resistance to the effects of weathering and light, and outstanding photostability of the incorporated stabilizer.
The materials to be stabilized can be, for example, oils, fats, waxes, cosmetics or biocides. A particularly interesting application is in polymeric materials which are present in plastics, rubbers, paints and other coating materials, photographic material or adhesives. Examples of polymers and other substrates which can be stabilized in this way are the following:
1. Polymers of monoolefins and diolefins, for example polypropylene, polyisobutylene, polybut-1-ene, poly-4-methylpent-1-ene, polyisoprene or polybutadiene, as well as polymers of cycloolefins, for example of cyclopentene or norbornene; furthermore polyethylene (which optionally can be crosslinked), for example high density polyethylene (HDPE), polyethylene of high density and high molecular mass (HDPE-HMW), polyethylene of high density and ultra-high molecular mass (HDPE-UHMW), medium density polyethylene (MDPE), low density polyethylene (LDPE), linear low density polyethylene (LLDPE), branched low density polyethylene (BLDPE).
Polyolefins, i.e. polymers of monoolefins exemplified in the preceding paragraph, in particular polyethylene and polypropylene, can be prepared by different, and especially by the following, methods:
a) radical polymerization (normally under high pressure and at elevated temperature); or
b) catalytic polymerization using a catalyst that normally contains one or more metals of group IVb, Vb, VIb or VIII of the Periodic Table. These metals usually have one or more ligands, such as oxides, halides, alcoholates, esters, ethers, amines, alkyls, alkenyls and/or aryls that may be either &pgr;- or &sgr;-coordinated. These metal complexes may be in the free form or fixed on substrates, for example on activated magnesium chloride, titanium(III) chloride, alumina or silicon oxide. These catalysts may be soluble or insoluble in the polymerization medium. The catalysts can be activated by themselves in the polymerization or further activators may be used, for example metal alkyls, metal hydrides, metal alkyl halides, metal alkyl o

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