Trisaryl-1,3,5-triazine ultraviolet light absorbers

Details Trisaryl-1,3,5-triazine ultraviolet light absorbers Trisaryl-1,3,5-triazine ultraviolet light absorbers

2001-04-11

2002-03-12

Sanders, Kriellion A. (Department: 1714)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Processes of preparing a desired or intentional composition...

C252S403000, C524S094000, C528S423000

Reexamination Certificate

active

06355708

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates generally to novel trisaryl-1,3,5-triazine compounds containing active (acidic) hydrogen atoms and the use thereof to protect against degradation by environmental forces, inclusive of actinic radiation (such as ultraviolet light), oxidation, moisture, atmospheric pollutants and combinations thereof.
2. Description of Related Art
Exposure to sunlight and other sources of ultraviolet radiation is 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.
A class 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-trazines, as well as processes for preparing and uses thereof, can be found in the following publications, all of which are incorporated by reference herein for all purposes as if fully set forth: U.S. Pat. No. 3,118,887, U.S. Pat. No. 3,242,175, U.S. Pat. No. 3,244,708, U.S. Pat. No. 3,249,608, U.S. Pat. No. 3,268,474, U.S. Pat. No. 3,423,360, U.S. Pat. No. 3,444,164, U.S. Pat. No. 3,843,371, U.S. Pat. No. 4,619,956, U.S. Pat. No. 4,740,542, U.S. Pat. No. 4,775,707, U.S. Pat. No. 4,826,978, U.S. Pat. No. 4,831,068, U.S. Pat. No. 4,962,142, U.S. Pat. No. 5,030,731, U.S. Pat. No. 5,059,647, U.S. Pat. No. 5,071,981, U.S. Pat. No. 5,084,570, U.S. Pat. No. 5,106,891, U.S. Pat. No. 5,185,445, U.S. Pat. No. 5,189,084, U.S. Pat. No. 5,198,498, U.S. Pat. No. 5,288,778, U.S. Pat. No. 5,298,067, U.S. Pat. No. 5,300,414, U.S. Pat. No. 5,322,868, U.S. Pat. No. 5,354,794, U.S. Pat. No. 5,364,749, U.S. Pat. No. 5,369,140, U.S. Pat. No. 5,410,048, U.S. Pat. No. 5,412,008, U.S. Pat. No. 5,420,204, U.S. Pat. No. 5,461,151, U.S. Pat. No. 5,476,937, U.S. Pat. No. 5,478,935, U.S. Pat. No. 5,489,503, U.S. Pat. No. 5,543,518, U.S. Pat. No. 5,538,840, U.S. Pat. No. 5,545,836, U.S. Pat. No. 5,563,224, U.S. Pat. No. 5,575,958, U.S. Pat. No. 5,591,850, U.S. Pat. No. 5,597,854, GB1033387, CH480091, CH484695, EP-A-0434608, EP-A-0444323, EP-A-0532006, EP-A-0649841, EP-A-0693483, EP-A-0704560, WO94/05645, WO95/22959 and WO96/28431.
Typically, the aforementioned aryl ring with the hydroxyl group ortho to the point of attachment to the triazine ring is based on resorcinol and, consequently, this aryl ring also contains a second substituent (either a hydroxyl group or a derivative thereof) para- to the point of attachment to the triazine ring. 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. For the purposes of the present invention, the former are referred to as “non-bondable” trisaryl-1,3,5-triazines and the latter are referred to as “bondable” trisaryl-1,3,5-triazines.
Many polymer additives (such as ultraviolet light stabilizers) may suffer from a disadvantage that they volatilize or migrate out of the polymer substrate to be protected, or that they are adsorbed (chemically or physically) by one or more systems components (such as pigments), thereby diminishing their effectiveness.
Bondable stabilizers have a potential advantage in this respect in that, depending on the bondable functionality and the particular polymer system to be stabilized, they can be chemically incorporated into a polymer structure via reaction of the bondable functionality either during polymer formation (such as in the case of polymerizing monomers or a crosslinking polymer system) or subsequently with a preformed polymer having appropriate reactive functionality. Accordingly, due to such bonding, migration of these UV absorbers between layers of multi-layer coatings and into polymer substrates and between coatings and their plastic substrates is greatly reduced.
Several of the previously incorporated references disclose bondable trisaryl-1,3,5-triazines. For example, previously incorporated U.S. Pat. No. 3,423,360, U.S. Pat. No. 4,962,142 and U.S. Pat. No. 5,189,084 disclose various bondable trisaryl-1,3,5-triazines and the incorporation of these compounds into polymers by chemical bonding. However, the inventors are unaware of any prior art which discloses the novel functionalized trisaryl-1,3,5-triazines of the present invention.
SUMMARY OF THE INVENTION
The present invention provides a new class of bondable trisaryl-1,3,5-triazines in which an aryl ring attached to the triazine ring (and preferably an aryl ring containing a hydroxyl group or “latent” hydroxyl group ortho- to the point of attachment to the triazine ring) is substituted with a bondable group, containing one or more active (acidic) hydrogen containing groups para- to the point of attachment to the triazine ring. As examples of such active (acidic) hydrogen containing groups may be mentioned 1,3-dicarbonyls, 1,3-diketones, 1,3-diesters (malonate esters), 1,3-ketoesters, beta-carbonyl cyano compounds, 1,3-sulfur compounds, 1,3-disulfones and 1,3-disulfoxides.
More specifically, the new trisaryl-1,3,5-triazines of the present invention have the following general formulas (I), (II) and (III):
wherein
each X is independently selected from hydrogen and a blocking group; each of Y and Z is independently selected from an aryl ring of the general formula (IV)
each R is independently selected from a hydrogen, a hydrocarbyl group and a functional hydrocarbyl group;
each R
1
, R
2
, R
4
, R
4
′ and R
4
″ is independently selected from hydrogen, hydrocarbyl, functional hydrocarbyl, —O(hydrocarbyl), —O(functional hydrocarbyl), —SR, halogen, —SO
2
R, —SO
3
R, —COOR, —COR, —OCOR, —NRR and cyano; and
each R
3
is independently selected from —R, —OR, —SR, halogen, —SO
2
R, —SO
3
R, —COOR, —COR, —NRR and cyano;
characterized in that at least one R group of a 4-position —OR group is selected from a group of the general formulas (V), (VI) and (VII):
wherein
A is selected from —O(O)C—; —C(O)—; —SO—; —SO
2
—; and —OSO
2
—;
each of A
1
and A
3
is independently selected from —COOR
7
; —COO
−
M
+
; —C(O)R
7
; —C(O)NR
7
R
8
; —CN; —NO
2
; —SO
2
R
7
; —SO
2
OR
7
; —SO
2
OR
7
and —SO
2
NR
7
R
8
;
A
2
is selected from —C(O)—; —R
9
C(O)—; —R
9
OC(O)—; —SO—; R
9
SO—; —SO
2
; —R
9
SO
2
—; and —R
9
OSO
2
—;
M
+
is a cationic moiety;
each of R
5
and R
9
is independently a hydrocarbylene group;
R
6
is selected from H and an alkyl of 1-4 carbon atoms; and
each of R
7
, R
8
and R
10
is independently selected from H, a hydrocarbyl group and a functional hydrocarbyl group.
These tris-aryl-1,3,5-triazines of the present invention have the added benefit of being capable of chemically bonding to appropriate polymer systems via the acidic active hydrogen. Since, in the above formulas, the acidic active hydrogen is from an active methylene or methine group, the further advantage of very stable carbon-carbon bonding is possible.
These trisaryl-1,3,5-triazines may in general be prepared via a number of procedures, but preferably by reacting a trisaryl-1,3,5-triazine precursor, having at least one aryl ring with an amino, amido and/or hydroxyl group containing —OR moiety para to the point of attachment to the triazine ring (and preferably also a hydroxyl group ortho to the point of attachment to the triazine ring), with an appropriate compound or compounds to functionalize the para position —OR group with a group of the above formula (V) and/or (VI). Further preferred process details are disclosed below.
The novel trisaryl-1,3,5-triazines of the present invention are particularly useful as ultraviolet light absorbe

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