JP3333789B2 - Infrared absorbing plate and manufacturing method thereof - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an infrared absorbing plate capable of selectively absorbing light and a method for producing the same.

[0002]

2. Description of the Related Art A conventional infrared absorbing material is disclosed in U.S. Pat. No. 3,692,688. Tungsten hexachloride and tin chloride are dissolved in methyl methacrylate syrup and cast and polymerized. It is described that an excellent material can be obtained. However, the material obtained by the cast polymerization has a higher transmittance than before the polymerization, and the ability to absorb infrared rays is greatly reduced. When this is exposed to ultraviolet light or sunlight, the infrared absorbing ability is first exhibited, but there is a problem that photochromism, which is gradually faded in a dark place, occurs, and the stability is low. Infrared absorbing dyes include metal complex-based dyes and anthraquinone-based dyes. However, when cast polymerization is carried out using a radical polymerization catalyst, there is a disadvantage that fading is large and absorption in the infrared region is greatly reduced.

[0003]

Means for Solving the Problems The present inventors have conducted intensive studies on an infrared-absorbing cast polymer plate having stable infrared-absorbing performance and a method for producing the same, and as a result, an aminium-based infrared-absorbing agent was converted to methyl methacrylate. It has been found that the object can be achieved by incorporating the compound in a monomer or a monomer mixture mainly composed of methyl methacrylate and performing cast polymerization with a peroxyester catalyst. That is, the present invention relates to 100 parts by weight of a monomer mixture comprising methyl methacrylate alone or 50% by weight or more of methyl methacrylate and 50% by weight or less of at least one monomer copolymerizable therewith, and an aminium-based infrared absorbing dye. 0.01
And a method for producing the same.

Hereinafter, the present invention will be described in detail. In the present invention, the copolymerizable monomers used for the methyl methacrylate monomer mixture include ethyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, cyclohexyl (meth) acrylate, -Hydroxyethyl (meth) acrylate,
(Meth) acrylates such as 2-hydroxypropyl (meth) acrylate and dimethylaminoethyl (meth) acrylate, ethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, neopentyl glycol di (meth) (Meth) acrylic acid polyesters such as acrylate and trimethylolpropane tri (meth) acrylate, (meth) acrylic acid, (meth) acrylamide, maleic acid, acrylonitrile, styrene, α-methylstyrene and the like. One or two or more monomers are used.

[0005] The type and amount of these copolymerizable monomers can be appropriately selected depending on the desired properties of the cast plate.

[0006] Specific examples of the aminium-based infrared absorber used in the present invention include Ka, manufactured by Nippon Kayaku Co., Ltd.
yasorb IRG-002 and the like.

The content of the above-mentioned aminium-based infrared absorber is 0.01 to 100 parts by weight of methyl methacrylate monomer or a monomer mixture mainly composed of methyl methacrylate.
To 5 parts by weight, preferably 0.02 to 2 parts by weight.
When the amount is less than 0.01 part by weight, the infrared ray absorbing ability is not sufficiently improved, and when the amount exceeds 5 parts by weight, the transmittance of visible light becomes low, so that it cannot be realized.

In the present invention, the peroxyester peroxide catalyst includes t-butylperoxyacetate, t-butylperoxyisobutyrate, t-butylperoxy-2-ethylhexanoate, and t-amylperoxy. 2-ethylhexanoate and the like can be mentioned.

The content of the above polymerization initiator is 0.01 to 5 parts by weight, preferably 0.05 to 3 parts by weight, based on 100 parts by weight of a methyl methacrylate monomer or a monomer mixture mainly composed of methyl methacrylate. Parts by weight.

[0010] The infrared absorbing plate of the present invention is desirably manufactured by a casting polymerization method usually performed by those skilled in the art. As a method of casting polymerization, methyl methacrylate alone or 50% by weight or more of methyl methacrylate and 50% by weight of at least one monomer copolymerizable therewith
A predetermined amount of an aminium-based infrared absorber is added to and dissolved in a monomer mixture composed of the following, and a peroxyester-based peroxide catalyst is further added to obtain a casting raw material. There is a method in which the raw material is injected between two glass sheets facing each other with the periphery sealed with a gasket and heated. The polymerization temperature varies depending on the type of polymerization initiator used, but is generally from 30 to 150C.

In the practice of the present invention, various additives,
For example, dyes and pigments used for coloring, stabilizers such as antioxidants and ultraviolet absorbers, flame retardants, polymerization regulators, release agents and the like can be added. The type and amount of these additives can be arbitrarily selected within a range that achieves the object of the present invention.

The infrared absorbing plate thus obtained can be used as an optical filter or a heat ray shielding plate, for example, a heat ray absorbing glazing material, a naked eye protection filter,
It is suitable for an infrared absorption filter for a semiconductor light receiving element.

[0013]

EXAMPLES The present invention will be described below with reference to specific examples, but the present invention is not limited to these examples. In the examples, parts represent parts by weight, and the transmission spectrum of the obtained infrared absorbing plate was measured with a spectrophotometer (U-3410, manufactured by Hitachi, Ltd.). Example 1 To 100 parts of methyl methacrylate, 0.055 parts of Kayasorb IRG-002 (manufactured by Nippon Kayaku Co., Ltd.) as an aminium-based infrared absorbing dye was added and dissolved. To this, Tinuvin P (CIBA-GEIG) was used as an ultraviolet absorber.
Y3), 0.03 parts, Zelec UN as release agent
0.2 parts (manufactured by DU PONT), t- as a polymerization catalyst
After adding and mixing 0.2 parts of amyl peroxy 2-ethylhexanoate, the mixture was injected into a mold formed by sandwiching a gasket between two parallel glass plates according to a conventional method.
The polymer was immersed in a water bath at 80 ° C. for 3 hours, and then heated in an air bath at 120 ° C. for 2 hours to complete the polymerization.

The transmission spectrum of the obtained resin plate was measured. The result is shown in FIG. Example 2 Five parts of neopentyl glycol dimethacrylate were mixed with 95 parts of methyl methacrylate, and 0.1 part of IRG-002 was added and dissolved therein. This is Tinuvin 3
27 (manufactured by CIBA-GEIGY), 0.2 parts, Zel
ec UN 0.2 parts and t-amyl peroxy 2-ethylhexanoate 0.5 part were added and mixed.
Polymerization was carried out in the same manner as in Example 1 to obtain a resin plate having a thickness of 3 mm.

The transmission spectrum of this resin plate is shown by A in FIG.
Shown in Example 3 0.0 parts of IRG-002 was added to 100 parts of methyl methacrylate.
8 parts were added and dissolved. After 0.1 part of Tinuvin 327, 0.2 part of Zelec UN and 0.3 part of t-amyl peroxy 2-ethylhexanoate were added and mixed, polymerization was carried out in the same manner as in Example 1 to obtain a plate. A 1 mm thick resin plate was obtained.

The transmission spectrum of this resin plate is shown by B in FIG.
Shown in Example 4 IRG-002 was added to 100 parts of methyl methacrylate in 0.0 parts.
4 parts were added and dissolved. After 0.1 part of Tinuvin 327, 0.2 part of Zelec UN and 0.2 part of t-amyl peroxy 2-ethylhexanoate were added and mixed, polymerization was carried out in the same manner as in Example 1 to obtain a plate. 5.5m thick
m was obtained.

The transmission spectrum of this resin plate is indicated by C in FIG.
Shown in Example 5 IRG-002 was added to 100 parts of methyl methacrylate in an amount of 0.0
55 parts were added and dissolved. After adding 0.03 part of Tinuvin P, 0.2 part of Zelec UN and 0.1 part of t-butyl peroxyisobutyrate thereto, and mixing,
Polymerization was carried out in the same manner as in Example 1 to obtain a resin plate having a thickness of 3 mm.

The transmission spectrum of this resin plate is shown by D in FIG.
Shown in Comparative Example 1 0.0% of IRG-002 was added to 100 parts of methyl methacrylate.
55 parts were added and dissolved. The Zelec UN is set to 0.
2 parts and 0.3 part of lauroyl peroxide which is a diacyl peroxide-based peroxide catalyst as a polymerization catalyst were added and mixed, followed by polymerization in the same manner as in Example 1 to obtain a sheet thickness of 3 m.
m was obtained.

FIG. 4 shows the transmission spectrum of the resin plate. The absorption in the infrared region was greatly reduced due to the fading during the polymerization.

[0020]

According to the present invention, as described above, an aminium-based infrared absorber is contained in a methyl methacrylate monomer or a monomer mixture mainly containing methyl methacrylate,
By performing cast polymerization with a peroxyester catalyst, a cast plate having good infrared absorption performance can be stably obtained.

[Brief description of the drawings]

FIG. 1 is a diagram showing a transmission spectrum.

FIG. 2 is a diagram showing a transmission spectrum.

FIG. 3 is a diagram showing a transmission spectrum.

FIG. 4 is a diagram showing a transmission spectrum.

[Explanation of symbols]

A is a transmission spectrum of the resin plate obtained in Example 2. B is a transmission spectrum of the resin plate obtained in Example 3. C is a transmission spectrum of the resin plate obtained in Example 4. D is a transmission spectrum of the resin plate obtained in Example 5.

──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-4-261406 (JP, A) JP-A-3-179003 (JP, A) JP-A-3-215561 (JP, A) JP-A-58-1983 225110 (JP, A) (58) Field surveyed (Int. Cl. ⁷ , DB name) C08F 2/00-2/60 C08F 20/00-20/70

Claims (2)

(57) [Claims] 1. Amine-based infrared absorbing dye, 100 parts by weight of methyl methacrylate alone or 100 parts by weight of a monomer mixture comprising 50% by weight or more of methyl methacrylate and 50% by weight or less of at least one monomer copolymerizable therewith. 0.01
An infrared absorbing plate comprising a polymerized and cured product of 〜5 parts by weight and 0.01-5 parts by weight of a peroxyester peroxide catalyst. 2. An aminium-based infrared absorbing dye is added to 100 parts by weight of a monomer mixture consisting of methyl methacrylate alone or 50% by weight or more of methyl methacrylate and 50% by weight or less of at least one monomer copolymerizable therewith. 0.01
A method for producing an infrared absorbing plate, comprising adding a polymer material containing 0.01 to 5 parts by weight of a peroxyester-based peroxide catalyst, pouring it into a mold, and performing cast polymerization.