Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Reexamination Certificate
2001-02-22
2002-12-31
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...
Reexamination Certificate
active
06500887
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a polymeric material composition having improved properties in terms of weatherability and resistance to discoloration by virtue of a specific triaryltriazine compound incorporated in the composition. The triaryltriazine compound has at least one aryl group which is a 2-hydroxyphenyl group having, at the 4-position thereof, an alkyl group substituted by a (meth)acryloyloxy group.
BACKGROUND OF THE INVENTION
Polymer materials such as polyethylene, polypropylene, styrene resin, polyvinyl chloride, polycarbonate, and polyester; organic pigments; and organic dyes may not endure prolonged use, due to deterioration caused by light and resultant discoloration or lowering of mechanical strength.
Conventionally, in order to prevent deterioration of such organic materials and to control the wavelength of light penetrating the materials, a variety of UV-absorbers have been used. Examples of such UV-absorbers include benzophenone, benzotriazole, 2,4,6-triaryltriazine, and cyanoacrylate compounds.
These UV-absorbers exhibit various UV absorption spectra attributed to the structures thereof. Also, the compatibility and volatility of the UV-absorbers differ depending on the material. Therefore, an appropriate UV-absorber is chosen in accordance with the intended use of the polymer material. Particularly, a thin film-like material employed as a protective layer must contain a large amount of UV-absorber in order to enhance the UV-shielding effect of the layer. Therefore, there is demand for an UV-absorber having excellent compatibility with a substrate layer, low volatility, and high absorption coefficient.
A 2,4,6-triaryltriazine UV-absorber exhibits a high absorption coefficient and excellent heat resistance. However, when the UV-absorber is incorporated into a polymer material, the UV-absorber may impart color to a resin of the material during processing, which is detrimental to practical use.
Japanese Patent Publication (kokoku) No. 42-25303 and Japanese Patent Application Laid-Open (kokai) No. 4-117410 disclose that, when a (meth)acryloyl-group-containing UV-absorber is incorporated into a skeleton of a polymer material through polymerization, or when the UV-absorber is oligomerized to thereby form a high-molecular-weight UV-absorber, the UV-absorber thus obtained exhibits persistent UV-absorbing effect in the polymer material. During the polymerization or oligomerization, the UV-absorber is copolymerized with a compound having an ethylenic unsaturated bond, and thus (meth)acryloyl groups present in the polymer material are lost. For this reason, it has never been expected that discoloration of polymer materials could be prevented if an UV-absorber is added into a polymer material without loss of (meth)acryloyl groups.
DISCLOSURE OF THE INVENTION
In view of the foregoing, the present inventors have performed extensive studies, and have found that a triazine compound represented by the following formula (I) having a substituent at a specific position thereof and having a (meth)acryloyl group exhibits UV-absorbing effects; and that a polymeric material composition containing the triazine compound exhibits excellent weatherability and excellent heat resistance without inducing discoloration of the organic material. The present invention has been accomplished on the basis of these findings.
Accordingly, the present invention provides a polymeric material composition comprising 100 parts by weight of a polymer material and 0.001-10 parts by weight of a triazine compound represented by the following formula (I):
(wherein A represents ring A; X and Y each independently represents ring A or ring B; R
1
represents a C1-C25 alkyl group substituted by a (meth)acryloyloxy group, wherein the alkyl group may further be substituted by a hydroxyl group, a C1-C8 alkoxy group, or a C1-C8 acyloxy group, or the alkyl group may contain, as an insertion, an oxygen atom, a sulfur atom, a carbonyl group, an ester group, an amido group, or an imino group; R
2
represents a hydrogen atom; R
3
, R
4
, R
5
and R
6
each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1-C12 alkyl group, a C1-C12 alkenyl group, a C1-C12 alkoxy group, a C1-C12 alkoxycarbonyl group, or an arylalkyl group, wherein the alkyl group, the alkoxy group, the alkoxycarbonyl group, and the arylalkyl group may be substituted by a hydroxyl group, a halogen atom, a C1-C12 alkyl group, a C1-C12 alkoxy group, a sulfonic acid group, a glycidyloxy group, a cyano group, an isocyanate group, or a (meth)acryloyl group, or, the alkyl group, the alkoxy group, the alkoxycarbonyl group, and the arylalkyl group may contain, as an insertion, an oxygen atom, a sulfur atom, a carbonyl group, an ester group, an amido group, or an imino group; and the substitution and the insertion may occur in combination, and R
3
represents a hydrogen atom in the case of R
3
being in the 5-position.) The present invention will next be described in more detail.
BEST MODES FOR CARRYING OUT THE INVENTION
Triazine Compounds
Examples of the alkyl group which is to be substituted by a (meth)acryloyloxy group to form a (meth)acryloyloxy group-substituted alkyl group R
1
include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-pentyl, tert-pentyl, hexyl, isohexyl, heptyl, octyl, isooctyl, sec-octyl, tert-octyl, and 2-ethylhexyl. Examples of the alkyl group having a substituent include 2-acetoxypropyl, 2-hydroxypropyl, and 2-butoxymethylethyl. Examples of constituent chains of the alkyl group, in which an oxygen atom or another atom is inserted, include polyoxyethylene and polyoxypropylene.
More specifically, examples of the group represented by R
1
include (meth)acryloyloxyalkyl groups such as acryloyloxyethyl, methacryloyloxyethyl, 2-hydroxy-3-methacryloyloxypropyl, 2-(2-methacryloyloxyethyloxy)ethyl, and 2-hydroxy-3-(2-methacryloyloxyethyloxy)propyl.
Examples of the alkyl groups represented by R
3
, R
4
, R
5
, or R
6
in formula (I) include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, tert-amyl, octyl, tert-octyl, decyl, undecyl, and dodecyl. Examples of the arylalkyl group include 1-methyl-1-phenylethyl, benzyl, and 2-phenylethyl.
Examples of the C1-C12 alkenyl groups represented by R
3
, R
4
, R
5
, or R
6
include linear or branched propenyl, butenyl, pentenyl, hexenyl, heptenyl, and octenyl. In such an alkenyl group, an unsaturated bond may be present at any position.
Examples of the C1-C12 alkoxy groups and the C1-C12 alkoxycarbonyl groups represented by R
3
, R
4
, R
5
, or R
6
include derivatives of alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, tert-amyl, octyl, tert-octyl, decyl, undecyl, and dodecyl. Examples of the arylalkyl group include a cumyl group and a phenylmethylene group. Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom.
Examples of the triazine compounds represented by formula (I), which are used in the present invention, include the following No. 1 to No. 6 compounds.
The method for synthesizing the triazine compounds of formula (I), which are used in the present invention, is not particularly limited, and the compounds may be synthesized by means of any customary method.
For example, any of the compounds may be synthesized by means of the following synthesis method: a method in which 2-(2,4-dihydroxyphenyl)-4,6-diaryl-s-triazine is reacted with glycidyl methacrylate, to thereby yield 2-(2-hydroxy-4-(2-hydroxy-3-methacryloyloxypropyloxy)phenyl)-4, 6-diaryl-s-triazine; a method in which 2-(2,4-dihydroxyphenyl)-4,6-diaryl-s-triazine is reacted with alkylene oxide to yield 2-(2-hydroxy-4-(2-hydroxyalkoxy)phenyl)-4,6-diaryl-s-triazine, followed by reaction with (meth)acrylic acid, to thereby yield 2-(2-hydroxy-4-(2-(meth)acryloyloxyalkoxy)phenyl)-4,6-aryl-s-triazine; or a method in which benzamidine hydrochloride is reacted with phenyl resorcylate to yield 2-(2,4-dihydroxyphenyl)-4,6-diphenyl-s-triazine, followed
Ayabe Takashi
Ishikawa Shin-ichi
Nanbu Yoko
Tobita Etsuo
Asahi Denka Kogyo K.K.
Nixon & Vanderhye PC
Sanders Kriellion A.
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