Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Reexamination Certificate
2001-09-27
2004-10-05
Raymond, Richard L. (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
C544S213000, C544S217000, C544S219000, C252S380000, C524S100000
Reexamination Certificate
active
06800757
ABSTRACT:
FIELD OF THE INVENTION
This invention relates generally to novel red-shifted triazines and their use to protect against degradation by environmental forces, such as actinic radiation, oxidation, moisture, atmospheric pollutants and combinations thereof.
BACKGROUND OF THE INVENTION
Exposure to sunlight and other sources of ultraviolet radiation are known to cause degradation of a variety of materials, especially polymeric materials. For example, polymeric materials such as plastics often discolor and/or become brittle as a result of prolonged exposure to ultraviolet light. Accordingly, a large body of art has been developed directed towards materials, such as ultraviolet light absorbers and stabilizers, which are capable of inhibiting such degradation.
Classes of materials known to be ultraviolet light absorbers are trisaryl-1,3,5-triazines, in which at least one of the aryl rings has a hydroxyl group ortho to the point of attachment to the triazine ring. In general this class of materials is well known in the art. Disclosures of a number of such trisaryl-1,3,5-triazines can be found in the patent literature such as those disclosed in U.S. Pat. Nos. 3,843,371 and 3,896,125.
Typically, the aforementioned phenyl ring with the hydroxyl group ortho to the point of attachment to the triazine ring is based on resorcinol and, consequently, this phenyl ring also contains a second substituent (either a hydroxyl group or a derivative thereof) para to the point of attachment to the triazine ring. For example, U.S. Pat. Nos. 3,118,887 and 3,244,708 disclose p-alkoxy-o-hydroxyphenyl triazines.
This second substituent can be “non-reactive,” as in the case of an alkyloxy group, or “reactive” as in the case of a hydroxyalkyloxy (active hydrogen reactive site) or (meth)acryloyl (ethylenic unsaturation reactive site) group.
A general disadvantage of trisaryl-1,3,5-triazines containing a resorcinol group is that they absorb less in the 360-400 nm region than other commercially available UV absorbers, e.g., hydroxyphenyl benzotriazoles. The spectral region from about 360 nm to about 400 nm is commonly known as upper wavelength UV light. An example where protection in the upper UV range is significant is epoxy resins, which are important primers in automotive and other industrial applications. Light can penetrate automotive clear and basecoats and destroy the epoxy primer at the primer/basecoat interface. This is then accompanied by loss of topcoat adhesion, even though the topcoat itself may still be in excellent condition. Exposure to high humidity facilitates this delamination phenomenon.
Increased absorbance in the upper UV region enhances the protection of substrates sensitive to longer wavelength ultraviolet light (near visible), such as primers, coatings, plastics, inks, photographic materials and fibers. Therefore, it is desirable to provide novel triazines with significant UV absorbance extending from the UV region (below about 360 nm in wavelength) into the upper UV region from about 360 nm to about 400 nm.
UV absorbance that is shifted toward the upper UV region is often referred to as red-shifted. This invention discloses novel red-shifted triazines, i.e., those comprising novel 1,3,5-triazine structures containing a 2-naphthol-derived substituent, that have significant UV absorbance in the upper UV region.
SUMMARY OF THE INVENTION
This invention relates to a novel red-shift triazine compound of Formula I:
where R
1
, R
2
, are the same or different and each is hydrogen, alkyl of 1 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, cycloalkyl of 5 to 25 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, aracyl of 6 to 24 carbons atoms, COR, CONRR′, and SO
2
R;
R
3
, R
4
, R
5
, R
6
and R
7
are the same or different and each is hydrogen, halogen, alkyl of 1 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, cycloalkyl of 5 to 25 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, aracyl of 6 to 24 carbons atoms, OR, NRR′, CONRR′, OCOR, CN, SR, SO
2
R, SO
3
H, SO
3
M, wherein M is an alkali metal, R and R′ are the same or different and each is hydrogen, alkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, cycloalkyl of 1 to 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, or aracyl of 6 to 24 carbons atoms, and Y is a direct bond, O, NR″, or S, wherein R″ is hydrogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, cycloalkyl of 1 to 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, or aracyl of 7 to 24 carbons atoms;
T is a direct bond, oxygen, NR′ or sulfur, Z is a hydrogen, halogen, substituted or unsubstituted alkyl of 1 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, aracyl of 7 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, cycloalkyl of 5 to 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, substituted or unsubstituted alkyl of 1 to 24 carbon atoms interrupted with at least one hetero atom, cycloalkyl of 5 to 24 carbon atoms interrupted with at least one hetero atoms, CONR′″R″″, SO
2
R′″ or Ar
2
wherein R′″ is substituted or unsubstituted alkyl group of 1 to 24 carbon atoms; R″″ is hydrogen or substituted or unsubstituted alkyl group of 1 to 24 carbon atoms;
where Ar
1
and Ar
2
are each independently a radical of Formula II:
where R
8
, R
9
, R
10
, R
11
, and R
12
are the same or different and each is hydrogen, halogen, alkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, aracyl of 6 to 24 carbon atoms, OR, NRR′, CONRR′, OCOR, CN, SR, SO
2
R, SO
3
H, SO
3
M, wherein M is an alkali metal, and optionally with either of R
8
and R
9
, R
9
and R
10
, R
10
and R
11
, or R
11
, and R
12
, taken together being a part of a saturated or unsaturated fused carbocyclic ring optionally containing O, N, or S atoms in the ring. Preferably the radical of Formula II is not a naphthyl substituted with a hydroxyl group ortho to the point of attachment to the triazine ring.
The novel red-shifted triazines of the present invention are particularly useful as ultraviolet light absorber additives for stabilizing a wide variety of materials including, for example, organic compounds, oils, fats, waxes, cosmetics, inks, dyes and biocides, and particularly various organic polymers (both cross-linked and non-cross-linked) used in applications such as photographic materials, plastics, rubbers, paints and other coatings, and adhesives, such as disclosed in a number of the previously incorporated references.
The present invention, consequently, also relates to a method for stabilizing a material by incorporating into such material, e.g., organic material, the inventive red-shifted triazine compounds in an amount effective to stabilize the material against the effects of actinic radiation, and the material so stabilized.
The novel red-shifted triazine compounds of the present invention are also effective as ultraviolet light screening agents in applications such as sunscreens and other cosmetic preparations, capstock layers for extruded polymers and laminated UV-screening window films, among others.
These and other features and advantages of the present invention will be more readily understood by those of ordinary skill in the art from a reading of the following detailed description.
REFERENCES:
patent: 3118887 (1964-01-01), Hardy et al.
patent: 3244708 (1966-04-01), Duennenberger et al.
patent: 3843371 (1974-10-01), Piller et al.
patent: 3896125 (1975-07-01), Helmo et al.
patent: 578
Cappadona Russell C.
Gupta Ram Baboo
Singh Hargurpreet
Balasubramanian Venkataraman
Cytec Technology Corp.
Jubinsky James A.
Raymond Richard L.
Schultz Claire M.
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