JPH0453892B2 - - Google Patents
Info
- Publication number
- JPH0453892B2 JPH0453892B2 JP60171792A JP17179285A JPH0453892B2 JP H0453892 B2 JPH0453892 B2 JP H0453892B2 JP 60171792 A JP60171792 A JP 60171792A JP 17179285 A JP17179285 A JP 17179285A JP H0453892 B2 JPH0453892 B2 JP H0453892B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- infrared absorber
- additives
- infrared
- examples
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000006096 absorbing agent Substances 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 9
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 8
- 230000002745 absorbent Effects 0.000 claims description 7
- 239000002250 absorbent Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 239000000654 additive Substances 0.000 description 29
- 239000000203 mixture Substances 0.000 description 16
- 230000000996 additive effect Effects 0.000 description 13
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
- 238000004898 kneading Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- -1 polyethylene Polymers 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000005033 polyvinylidene chloride Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920001283 Polyalkylene terephthalate Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical group [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Optical Filters (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
Description
「産業上の利用分野」
本発明は赤外線吸収剤の耐光堅牢度向上法に関
する。更に詳しくは特定な化合物を共存せしめる
ことによる特定の赤外線吸収剤の耐光堅牢度向上
法に関する。
「従来の技術」
近年赤外線吸収剤は広範な分野に利用されるよ
うになつた。例えば光学的記録媒体の分野におい
ては、赤外線吸収剤を含む層をアクリル樹脂板、
ポリカーボネート樹脂板等の基板上に形成せしめ
これに適当な光、例えばレーザー光を照射するこ
とにより情報を記録することが行われている。又
赤外線吸収剤をバインダーと有機溶媒との混合物
に混合し例えば透明なアクリル樹脂板に塗布する
ことにより赤外領域の光線に対する光遮断材（フ
イルター）が製造されている。更に赤外線吸収剤
をメチルメタクリレート樹脂のような樹脂に練り
込み成形することにより赤外領域の光が遮断され
たメガネ等として用いることも、行われている。
式
（式(1)においてＲはアルキル基を、R′は炭素
総数２〜６のアルキルアミノ基又はハロゲン原子
で置換されていてもよいフエニル基を、Ｘは陰イ
オンを表す）
で表される赤外線吸収剤も前記したような用途に
使用されている。
「発明が解決しようとする問題点」
前記式(1)で表される赤外線吸収剤はすぐれた赤
外線吸収能を有するがその耐光堅牢度が十分でな
いという欠点があり、そのため高い耐光堅牢度を
有するような用途、目的の為にはその使用が制限
されている。
「問題点を解決する為の手段」
本発明者らは前記したような時題点を解決すべ
く鋭意研究を重ねた結果本発明に至つたものであ
り、即ち本発明は式
（式(1)においてＲはアルキル基を、R′は炭素
総数２〜６のアルキルアミノ基又はハロゲン原子
で置換されていてもよいフエニル基を、Ｘは陰イ
オンを表す）
で表される赤外線吸収剤に下記(2)，(3)，(4)の化合
物
（式(2)，(3)及び(4)においてＲは前記と同じ意味
を、X′は陰イオンを表す。又式(3)においてＡは
置換していてもよいフエニル基又はナフタレン基
を表す）又はアセチルアセトンのNi（），Cu
（），Mn（）若しくはCo（）キレート化物か
ら選ばれる化合物の１種又は２種以上を併用する
ことを特徴とする式(1)で表される赤外線吸収剤の
耐光堅牢度向上法を提供する。
本発明において式(1)で表される赤外線吸収剤及
び式(2)，(3)，(4)及び前記アセチルアセトン金属キ
レート化合物（以後これらを添加剤という）の具
体的な例としては次のような化合物が挙げられ
る。
式(1)の赤外線吸収剤の例（Ｒ，R′，X-は各各
式(1)におけるものである。）
"Industrial Application Field" The present invention relates to a method for improving the light fastness of an infrared absorbent. More specifically, the present invention relates to a method for improving the light fastness of a specific infrared absorber by coexisting a specific compound. "Prior Art" In recent years, infrared absorbers have come to be used in a wide range of fields. For example, in the field of optical recording media, a layer containing an infrared absorber is formed on an acrylic resin plate,
Information is recorded by forming on a substrate such as a polycarbonate resin plate and irradiating it with appropriate light, such as laser light. Also, a light blocking material (filter) for light in the infrared region is manufactured by mixing an infrared absorber with a mixture of a binder and an organic solvent and applying the mixture to, for example, a transparent acrylic resin plate. Furthermore, by kneading an infrared absorber into a resin such as methyl methacrylate resin and molding it, the material is used as glasses that block light in the infrared region. formula (In formula (1), R represents an alkyl group, R' represents an alkylamino group having 2 to 6 carbon atoms or a phenyl group which may be substituted with a halogen atom, and X represents an anion) Absorbents are also used in the applications described above. "Problems to be Solved by the Invention" Although the infrared absorbent represented by the above formula (1) has excellent infrared absorption ability, it has the drawback that its light fastness is insufficient; therefore, it has a high light fastness. Its use is restricted for such uses and purposes. "Means for Solving the Problems" The present inventors have conducted extensive research to solve the above-mentioned current problems, and have arrived at the present invention. (In formula (1), R represents an alkyl group, R' represents an alkylamino group having 2 to 6 carbon atoms or a phenyl group which may be substituted with a halogen atom, and X represents an anion) The following compounds (2), (3), and (4) are used as an absorbent. (In formulas (2), (3) and (4), R has the same meaning as above, and X' represents an anion. In formula (3), A represents an optionally substituted phenyl group or naphthalene group. ) or acetylacetone Ni (), Cu
Provided is a method for improving the light fastness of an infrared absorber represented by formula (1), which comprises using one or more compounds selected from chelates of Mn(), Mn(), or Co() in combination. do. In the present invention, specific examples of the infrared absorber represented by formula (1), formulas (2), (3), and (4), and the acetylacetone metal chelate compound (hereinafter referred to as additives) are as follows. Compounds such as: Examples of infrared absorbers of formula (1) (R, R', X - are those in each formula (1))
【表】【table】
【表】
式(2)の添加剤の例（Ｒ及びX-は式(2)における
ものである）。[Table] Examples of additives of formula (2) (R and X - are as in formula (2)).
【表】
式(3)の添加剤の例（Ｒ，Ａ，およびX′は式(3)
におけるものである）[Table] Examples of additives of formula (3) (R, A, and X' are of formula (3)
)
【表】【table】
【表】
式(4)の添加剤の例（Ｒ，及びX′-は式(4)におけ
るものである）[Table] Examples of additives of formula (4) (R and X′ - are those in formula (4))
【表】
アセチルアセトンの金属キレート化合物の例
No.
（）−１ Ni（）アセチルアセトナート
〃 −２ Cu（）アセチルアセトナート
〃 −３ Mn（）アセチルアセトナート
〃 −４ Co（）アセチルアセトナート
本発明で式(1)の赤外線吸収剤は前記した添加剤
の１種又は２種以上を併用して後記するような塗
布法又は練り込み法によつて適用されるものであ
るが塗布法で適用する場合、式(1)の赤外線吸収
剤、及び添加剤を溶解する為の溶剤としてはジク
ロロメタン、ジクロロエタン、アセトン、メチル
エチルケトン等を挙げることが出来る。更にバイ
ンダーを併用して塗布する場合の溶剤の例として
はメチルエチルケトン、メチルイソブチルケト
ン、ジメチルホルムアミド、酢酸メチル、酢酸エ
チル、トルエン、キシレン、メタノール、エタノ
ール、イソプロピルアルコール、ジメチルホルム
アミド、ジクロロエタン等を挙げることが出来
る。そしてバインダーを併用する場合用いられる
バインダーの例としてはフエノール系、アルキツ
ド系、尿素メラミン系、エポキシ系、不飽和ポリ
エステル系、シリコン系、ポリウレタン系、ポリ
アクリレート系、ポリ酢酸ビニール系、ポリスチ
レン系樹脂等が挙げられる。
又式(1)の赤外線吸収剤を前記添加剤を併用して
樹脂に練り込み法で適用する場合の樹脂の例とし
てはポリアミド系、ポリスチレン系、ポリアクリ
レート系、ポリメタクリレート系、ポリカーボネ
ート系、セルローストリアセテート系、ポリエチ
レン系、ポリプロピレン系、ポリ塩化ビニル系、
ポリ塩化ビニリデン系、ポリアルキレンテレフタ
レート系、不飽和ポリエステル系、アクリル−ス
チレン系樹脂などが挙げられる。
式(1)に赤外線吸収剤に対する前記添加剤の添加
比率は赤外線吸収剤1.0に対し添加剤0.05〜5.0、
好ましくは0.3〜1.5である。
式(1)の赤外線吸収剤と前記添加剤を塗布して用
いる場合の基質の例としてはポリアクリレート
系、ポリメタクリレート系、ポリカーボネート
系、セルローストリアセテート系、ポリエチレン
系、ポリプロピレン系、ポリ塩化ビニル系、ポリ
塩化ビニリデン系、PVA系、ポリエステル系、
ポリアミド系、ポリイミド系、ポリスルホン系、
ポリエーテル系、ポリスチレン系、ポリアクリル
ニトリル系樹脂や必要によりこれ等の樹脂の表面
をシリコン系合成樹脂などで保護層を設けたもの
及び各種ガラス、セラミツクス、金属などが挙げ
られる。
塗布の方法としては式(1)の赤外線吸収剤と前記
添加剤の１種又は２種以上の混合物を前記した溶
剤に溶解して塗布するか赤外線吸収剤と前記添加
物を前記した溶剤に別々に溶解してから混合して
添布する。塗布法としてスプレー、或いはスピン
ナーを用いて前記したような樹脂の基板又はフイ
ルムに塗布する。又バインダーを併用する場合は
バインダーと溶媒の混合物に該赤外線吸収剤及び
添加剤を溶解せしめた液を基板又はフイルムにス
プレー、スピンナー、バーコーター、アプリケー
ター、グラビヤコーター等を用いて塗布する。
この場合基板又はフイルム上にまず添加剤の層
を設けその上に赤外線吸収剤の層を設けるか又は
その逆の順序によつて赤外線吸収剤と添加剤とか
らなる層を設けること相明数る。
練り込み法による場合は式(1)の赤外線吸収剤、
前記添加剤及び樹脂と混合し加熱溶融し、射出成
形機等で基板又はフイルム状に成型する。この場
合樹脂１００に対して式(1)の赤外線吸収剤は通常
0.001〜1.0の範囲で又添加剤は前記したような範
囲で用いられる。
本発明の方法によつて式(1)の赤外線吸収剤が適
用された場合その耐光堅牢度が飛躍的に向上する
ので従来その耐光性が不十分なため使用の制限さ
れていた分野にも式(1)の赤外線吸収剤が使われる
ようになり又従来から用いられている分野にあつ
てもその耐光堅牢度が飛躍的に向上したので性能
の一層の改善がはかられた。
「実施例」
実施例によつて本発明を更に詳細に説明する。
実施例 １
（）−４の赤外線吸収剤 １ｇ
（）−a9の化合物（添加剤） １ｇ
ジクロロエタン 100ml
からなる溶液をアクリル板上にスピンナーを使用
して、2000r.p.mでコートした。この試験片を(A)
とする。比較例として、上記組成から（）−a9
の化合物を除いた組成の溶液を上記同様にコート
し、この試験片を(B)とし耐光試験を行つた。
耐光試験機はスガ試験機(株)製、Xenon Fade
Meter（型式FA−25X型、容量6KVA）を用い
た。
露光前及び一定時間露光後のλmaxにおける吸
光度を測定し、残存率Ｈを下記の式により算出し
た。結果は表の通りであつた。
Ｈ＝一定時間露光後の吸光度／露光前の吸光度×100
（％）
Ｈの値（％）の大きいもの程耐光堅牢度が良好な
ことを示す。
露光時間
試験片 10時間 82時間 154時間
(A) 100.0 99.6 99.4
(B) 88.6 ０ −
試験片(A)の残存率がたかく耐光堅牢度がすぐれ
ていることがわかる。
実施例 ２〜４
実施例１において添加剤を下記の表のように変
える以外は実施例１と同様な操作を行つて次の結
果をえた。（Ｈの値（％））
露光時間
実施例 添加剤 82時間 154時間
２ （）−a10 97.6 96.1
３ （）−c9 93.9 89.1
４ （）−b3 98.2 96.3
実施例 ５
（）−７の赤外線吸収剤 1.0ｇ
（）−１の化合物（添加剤） 0.3ｇ
ジクロロエタン 100ml
からなる溶液を実施例１と同様にコートしこの試
験片を(A)とする。比較例として、上記組成から
（）−１を除いて作製した試験片を(B)とする。実
施例１と同様にして行つた耐光試験によるＨの値
（％）は以下の通りであつた。
露光時間
試験片 82時間 154時間
(A) 97.5 31.4
(B) 88.6 ０
実施例 ６〜26
式(1)の赤外線吸収剤 １ｇ
添加剤 １ｇ
ジクロロエタン 100ml
からなる溶液を実施例１と同様にコートし、試験
片を作製し、耐光試験を行いＨの値（％）を算出
した。結果は以下の通りであつた。[Table] Examples of metal chelate compounds of acetylacetone No. ()-1 Ni () acetylacetonate 〃 -2 Cu () acetylacetonate 〃 -3 Mn () acetylacetonate 〃 -4 Co () acetylacetonate Book In the invention, the infrared absorber of formula (1) is applied by a coating method or a kneading method as described later using one or more of the above-mentioned additives, but it is applied by a coating method. In this case, examples of the solvent for dissolving the infrared absorber of formula (1) and additives include dichloromethane, dichloroethane, acetone, and methyl ethyl ketone. Furthermore, examples of solvents used when coating with a binder include methyl ethyl ketone, methyl isobutyl ketone, dimethyl formamide, methyl acetate, ethyl acetate, toluene, xylene, methanol, ethanol, isopropyl alcohol, dimethyl formamide, dichloroethane, etc. I can do it. Examples of binders that can be used in combination with binders include phenolic, alkyd, urea-melamine, epoxy, unsaturated polyester, silicone, polyurethane, polyacrylate, polyvinyl acetate, and polystyrene resins. can be mentioned. Examples of resins in which the infrared absorber of formula (1) is applied in combination with the above additives by kneading into the resin include polyamide, polystyrene, polyacrylate, polymethacrylate, polycarbonate, and cellulose. Triacetate-based, polyethylene-based, polypropylene-based, polyvinyl chloride-based,
Examples include polyvinylidene chloride resins, polyalkylene terephthalate resins, unsaturated polyester resins, and acrylic-styrene resins. In formula (1), the addition ratio of the additive to the infrared absorber is 0.05 to 5.0 of the additive to the infrared absorber of 1.0,
Preferably it is 0.3 to 1.5. Examples of substrates in which the infrared absorber of formula (1) and the additives are coated include polyacrylate-based, polymethacrylate-based, polycarbonate-based, cellulose triacetate-based, polyethylene-based, polypropylene-based, polyvinyl chloride-based, Polyvinylidene chloride, PVA, polyester,
Polyamide-based, polyimide-based, polysulfone-based,
Examples include polyether-based, polystyrene-based, polyacrylonitrile-based resins, resins whose surfaces are provided with a protective layer of silicone-based synthetic resin, etc., as well as various glasses, ceramics, and metals. The method of application is to dissolve one or more of the infrared absorber of formula (1) and the additives in the above-mentioned solvent, or to apply the infrared absorber and the additives separately in the above-mentioned solvent. Dissolve it in water, mix and apply. As a coating method, a spray or a spinner is used to coat the resin substrate or film as described above. When a binder is used in combination, a solution prepared by dissolving the infrared absorber and additives in a mixture of the binder and a solvent is applied to the substrate or film using a spray, spinner, bar coater, applicator, gravure coater, or the like. In this case, first a layer of the additive is provided on the substrate or film, and then a layer of the infrared absorber is provided thereon, or a layer consisting of the infrared absorber and the additive is provided in the reverse order. . When using the kneading method, the infrared absorber of formula (1),
The mixture is mixed with the additives and resin, heated and melted, and molded into a substrate or film using an injection molding machine or the like. In this case, the infrared absorber of formula (1) is usually
The range is from 0.001 to 1.0, and additives are used in the ranges described above. When the infrared absorbing agent of formula (1) is applied by the method of the present invention, its light fastness is dramatically improved, so that it can be used in fields where its use was previously restricted due to insufficient light resistance. Infrared absorbers (1) have come into use, and their light fastness has improved dramatically even in the fields where they have been traditionally used, leading to further improvements in performance. "Example" The present invention will be explained in more detail with reference to Examples. Example 1 A solution consisting of 1 g of the infrared absorber of ()-4 ()-a 9 (additive) and 100 ml of dichloroethane was coated on an acrylic plate at 2000 rpm using a spinner. This test piece (A)
shall be. As a comparative example, from the above composition ()−a 9
A solution having the composition except for the compound was coated in the same manner as above, and this test piece was used as (B) and a light resistance test was conducted. The light resistance tester is Xenon Fade manufactured by Suga Test Instruments Co., Ltd.
A meter (model FA-25X, capacity 6KVA) was used. The absorbance at λmax before exposure and after exposure for a certain period of time was measured, and the residual rate H was calculated using the following formula. The results were as shown in the table. H = Absorbance after exposure for a certain period of time / Absorbance before exposure x 100
(%) The larger the H value (%), the better the light fastness. Exposure time test piece 10 hours 82 hours 154 hours (A) 100.0 99.6 99.4 (B) 88.6 0 - It can be seen that the survival rate of the test piece (A) is high and the light fastness is excellent. Examples 2 to 4 The same operations as in Example 1 were performed except that the additives were changed as shown in the table below, and the following results were obtained. (Value of H (%)) Exposure time Example Additive 82 hours 154 hours 2 ()-a 10 97.6 96.1 3 ()-c 9 93.9 89.1 4 ()-b 3 98.2 96.3 Example 5 ()-7 A solution consisting of 1.0 g of infrared absorber ()-1 (additive) 0.3 g and 100 ml of dichloroethane was coated in the same manner as in Example 1, and this test piece was designated as (A). As a comparative example, a test piece prepared by removing ()-1 from the above composition is designated as (B). The H values (%) determined by the light fastness test conducted in the same manner as in Example 1 were as follows. Exposure time Test piece 82 hours 154 hours (A) 97.5 31.4 (B) 88.6 0 Examples 6 to 26 A solution consisting of 1 g of infrared absorber of formula (1), 1 g of additive, and 100 ml of dichloroethane was coated in the same manner as in Example 1, A test piece was prepared, a light resistance test was conducted, and the value of H (%) was calculated. The results were as follows.
【表】【table】
【表】
実施例 27
（）−11の赤外線吸収剤 0.3ｇ
（）−a5（添加剤） 0.05ｇ
ニトロセルロース 100ｇ
メタノール 20ｇ
メチルエチルケトン 10ｇ
トルエン 10ｇ
からなる組成液を磁製ボールミル中で16時間混合
し、１mm厚のポリエステルフイルム上へNo.12バー
コーターを用いて塗布し自然乾燥した。この試験
片を(A)とする。比較例として、上記組成から、
（）−a5の添加剤を除いた組成液で前記同様にし
て試験片(B)を作製した。(A)(B)について実施例１と
同様に耐光試験を行いＨの値（％）を算出した。
結果は以下の通りであつた。[Table] Example 27 A composition solution consisting of ()-11 infrared absorber 0.3 g ()-a 5 (additive) 0.05 g, nitrocellulose 100 g, methanol 20 g, methyl ethyl ketone 10 g, and toluene 10 g was mixed in a porcelain ball mill for 16 hours. It was applied onto a 1 mm thick polyester film using a No. 12 bar coater and air-dried. This test piece is designated as (A). As a comparative example, from the above composition,
()-a A test piece (B) was prepared in the same manner as described above using the composition solution excluding the additive 5 . A light fastness test was performed on (A) and (B) in the same manner as in Example 1, and the H value (%) was calculated.
The results were as follows.
【表】
実施例 28
（）−３の赤外線吸収剤 0.3ｇ
（）−c5（添加剤） 0.3ｇ
アクリルメラミンクリヤー 100ｇ
メチルイソブチルケトン 15ｇ
トルエン ５ｇ
酢酸エチル ５ｇ
の組成液を用いて実施例27と同様にして添加剤の
入つたものと入つていない試験片(A)，(B)を作製
し、耐光試験を行つた結果は以下の通りであつ
た。[Table] Infrared absorber of Example 28 ()-3 0.3g ()-c 5 (additive) 0.3g Acrylic melamine clear 100g Methyl isobutyl ketone 15g Toluene 5g Ethyl acetate 5g Using the composition solution of Example 27 Test pieces (A) and (B) with and without additives were prepared in the same manner, and a light resistance test was conducted.The results were as follows.
【表】
実施例 29
（）−４の赤外線吸収剤 0.03ｇ
（）−１（添加剤） 0.03ｇ
ポリメチルメタクリレート樹脂 100ｇ
上記組成物を加熱ニーダーで10分間混練した
後、混合物を取り出し冷却固化後ハンマーミルで
粗粉砕し、次に射出成形機で厚さ１mmのブレート
に成形した。
この試験片を(A)とする。比較例として上記組成
物から（）−１の添加剤を除いた組成物につい
て前記と同様にして試験片(B)を作製した。スガ試
験機(株)製スタンダード紫外線ロングライフ・フエ
ードメーター（型式FAL−3H型、電源容量200V
7KVA 50Hz）を用い耐光試験を行い、以下の結
果を得た。（Ｈの値、％）[Table] Example 29 Infrared absorber of ()-4 0.03g ()-1 (additive) 0.03g Polymethyl methacrylate resin 100g After kneading the above composition in a heating kneader for 10 minutes, the mixture was taken out and cooled and solidified. It was coarsely ground using a hammer mill, and then molded into a plate with a thickness of 1 mm using an injection molding machine. This test piece is designated as (A). As a comparative example, a test piece (B) was prepared in the same manner as above using a composition obtained by removing the additive ()-1 from the above composition. Standard ultraviolet long life fade meter manufactured by Suga Test Instruments Co., Ltd. (model FAL-3H, power capacity 200V)
A light resistance test was conducted using 7KVA 50Hz) and the following results were obtained. (value of H, %)
【表】
「発明の効果」
式(1)に示される赤外線吸収剤を適用するにあた
り特定の添加剤を使用することによつて該赤外線
吸収剤の耐光堅牢度を飛躍的に向上させることが
出来た。[Table] "Effects of the Invention" By using specific additives when applying the infrared absorbent shown in formula (1), the light fastness of the infrared absorbent can be dramatically improved. Ta.
Claims (1)
総数２〜６のアルキルアミノ基又はハロゲン原子
で置換されていてもよいフエニル基を、Ｘは陰イ
オンを表す） で表される赤外線吸収剤に下記(2)，(3)，(4)の化合
物 （式(2)，(3)及び(4)においてＲは前記と同じ意味
を、X′は陰イオンを表す。又式(3)においてＡは
置換していてもよいフエニル基又はナフタレン基
を表す） 又はアセチルアセトンのNi（），Cu（），Mn
（）若しくはCo（）キレート化物 から選ばれる化合物の１種又は２種以上を併用す
ることを特徴とする式(1)で表される赤外線吸収剤
の耐光堅牢度向上法。[Claims] 1 formula (In formula (1), R represents an alkyl group, R' represents an alkylamino group having 2 to 6 carbon atoms or a phenyl group which may be substituted with a halogen atom, and X represents an anion) The following compounds (2), (3), and (4) are used as an absorbent. (In formulas (2), (3) and (4), R has the same meaning as above, and X' represents an anion. In formula (3), A represents an optionally substituted phenyl group or naphthalene group. ) or acetylacetone Ni(), Cu(), Mn
A method for improving the light fastness of an infrared absorber represented by formula (1), which comprises using one or more compounds selected from Co() and Co() chelates.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60171792A JPS6232132A (en) | 1985-08-06 | 1985-08-06 | Improvement of light fastness of infrared absorber |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60171792A JPS6232132A (en) | 1985-08-06 | 1985-08-06 | Improvement of light fastness of infrared absorber |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6232132A JPS6232132A (en) | 1987-02-12 |
| JPH0453892B2 true JPH0453892B2 (en) | 1992-08-27 |
Family
ID=15929780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60171792A Granted JPS6232132A (en) | 1985-08-06 | 1985-08-06 | Improvement of light fastness of infrared absorber |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6232132A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0796335B2 (en) * | 1987-10-27 | 1995-10-18 | キヤノン株式会社 | Optical recording medium |
| JP2000007871A (en) * | 1998-06-23 | 2000-01-11 | Kureha Chem Ind Co Ltd | Resin composition and its production, optical filter and device equipped with the same, and athermanous filter, optical fiber and glass lens |
| EP1385024B1 (en) | 2001-05-01 | 2010-05-19 | Bridgestone Corporation | Near infrared absorbtion film |
| US8865293B2 (en) | 2008-12-15 | 2014-10-21 | 3M Innovative Properties Company | Optically active materials and articles and systems in which they may be used |
| WO2019146506A1 (en) * | 2018-01-25 | 2019-08-01 | キヤノン株式会社 | Compound, liquid composition, thermal transfer recording sheet, toner, resist composition for color filter, and color filter |
-
1985
- 1985-08-06 JP JP60171792A patent/JPS6232132A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6232132A (en) | 1987-02-12 |
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