Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Reexamination Certificate
1999-06-18
2001-10-23
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...
C544S215000, C544S216000, C252S403000
Reexamination Certificate
active
06306939
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates generally to novel poly-trisaryl-1,3,5-triazine carbamates and the use thereof to protect against actinic radiation.
2. Description of Related Art
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.
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-triazines 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. Nos. 3,118,887, 3,242,175, 3,244,708, 3,249,608, 3,268,474, 3,843,371, 4,619,956, 4,740,542, 4,775,707 4,826,978, 4,962,142, 5,030,731, 5,071,981, 5,084,570, 5,106,891, 5,185,445, 5,189,084, 5,198,498, 5,288,778, 5,298,067, 5,322,868, 5,354,794, 5,369,140, 5,412,008, 5,420,204, 5,461,151 and 5,478,935; Canadian Patent Documents CA A1-2162645 and CA 2,032,669; UK Patent Documents GB1033387 and GB-A-2293823; Swiss Patent Documents CH480091 and CH484695; European Patent Documents EP-A-0434608, EP-A-0434619, EP-A-0444323, EP-A-0649841, EP-A-0654469, EP-A-0704437, EP-A-0706083; and PCT Patent Documents 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. The former are typically 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 absorbed (chemically or physically) by one or more systems components (such as pigments), thereby diminishing their effectiveness.
Although the presently claimed poly triazine carbamates are not bondable, it is believed that due to their high molecular weight, these triazines will exhibit higher permanence due to reduced volatility and reduced migration within the materials in which they are employed. In particular, it is believed that these triazines will exhibit greater thermal stability than other carbamate containing triazines formed directly from phenolic systems, particularly those in which the carbamate group is bonded directly to the aromatic ring.
EP 434,619 and CA 2,032,669 generically disclose various bondable phenolic carbamoyl triazines and the incorporation of these compounds into polymers by chemical bonding. Additionally, U.S. Pat. No. 5,354,794 discloses generically triazines with one or more carbonyl and/or ester groups. However, the inventors are unaware of any prior art which discloses the novel poly-trisaryl-1,3,5-triazine carbamates of the present invention.
SUMMARY OF THE INVENTION
The present invention provides a new class of trisaryl-1,3,5-triazines which comprise a carbamate triazine polymer. More specifically, the new poly-trisaryl-1,3,5-triazine carbamates of the present invention have the following general formulas (I), (II) and (III):
wherein
A is a polyvalent hydrocarbyl or a heterocyclic ring;
each X is independently selected from hydrogen, allyl, —COR
a
, —SO
2
R
b
, —SiR
c
R
d
R
e
, —PR
f
R
g
, and —POR
f
R
g
;
each of Y and Z are the same or different, and are independently selected from an aryl ring of the general formula (IV);
each R is independently selected from a hydrocarbyl group, a functional hydrocarbyl group and a hydroxy alkyl amide such as —CH
2
CONC
4
H
9
(CH
2
)
2
OH;
each R′ is independently selected from a hydrocarbylene group, a functional hydrocarbylene group and a group such as —CH
2
CONC
4
H
9
(CH
2
)
2
—;
each R
a
is independently selected from C
1
-C
8
allyl, halogen-substituted C
1
-C
8
alkyl, C
5
-C
12
cycloalkyl, C
2
-C
8
alkenyl, —CH
2
—CO—CH
3
, C
7
-C
12
aralkyl, C
1
-C
12
alkoxy, or phenyl which is unsubstituted or substituted by C
1
-C
12
alkyl, C
1
-C
4
alkoxy, halogen and/or benzyl;
each R
b
is independently selected from C
1
-C
12
alkyl, C
6
-C
10
aryl, or C
7
-C
18
alkylaryl;
each R
c
, R
d
, and R
e
is independently selected from C
1
-C
18
alkyl, cyclohexyl; phenyl, or C
1
-C
18
alkoxy;
each R
f
and R
g
is independently selected from C
1
-C
12
alkoxy, phenoxy, C
1
-C
12
alkyl, C
5
-C
12
cycloalkyl, benzyl, tolyl, or phenyl;
each R
1
, R
2
and R
4
is independently selected from hydrogen, hydrocarbyl, functional hydrocarbyl, —O(hydrocarbyl), —O(functional hydrocarbyl), —SR, halogen, —SO
3
R, —COOR, —COR, —OCOR, —NRR and cyano; and
each R
3
is independently selected from R, —OR, —SR, halogen, —SO
3
R, —COOR, —COR, —NRR and cyano.
n is from 2 up to about 50
These poly-trisaryl-1,3,5-triazine carbamate polymers may in general be prepared via a number of procedures described in the previously incorporated references, but preferably by reacting two or more trisaryl-1,3,5-triazine precursors, each having at least one aryl ring with a hydroxyl group ortho to the point of attachment to the triazine ring, such aryl ring being further substituted by a hydroxyl functional —O(hydrocarbyl) group, (and preferably the hydrocarbyl group para to the point of attachment to the triazine ring), with a divalent hydrocarbyl linking agent such as a diisocyanate, or a trivalent hydrocarbyl linking agent such as a triisocyanate to form the compounds of Formulas (I)-(III). Further preferred process details are disclosed below.
The novel poly-trisaryl-1,3,5-triazine carbamates 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, dyes and biocides, and particularly various organic polymers (both crosslinked and non-crosslinked) 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 novel poly-trisaryl-1,3,5-triazine carbamate in an amount effective to stabilize the material against the effects of actinic radiation, and the material so stabilized.
The novel poly-trisaryl-1,3,5-triazine carbamates 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. The present invention, consequently, also relates to a method for screening ultraviolet light from a substrate by applying to such substrate a layer of a composition comprising the novel poly-trisaryl-1,3,5-triazine carbamates, and the substrate so screened.
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.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The Poly-Trisaryl
Gupta Ram Baboo
Jakiela Dennis John
Ciba Specialty Chemicals Corporation
Sanders Kriellion A.
Stevenson Tyler A.
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