JPH0657798B2 - Blue dye for filters - Google Patents
Blue dye for filtersInfo
- Publication number
- JPH0657798B2 JPH0657798B2 JP28674986A JP28674986A JPH0657798B2 JP H0657798 B2 JPH0657798 B2 JP H0657798B2 JP 28674986 A JP28674986 A JP 28674986A JP 28674986 A JP28674986 A JP 28674986A JP H0657798 B2 JPH0657798 B2 JP H0657798B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- parts
- dye
- filters
- resin
- 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
- 239000001045 blue dye Substances 0.000 title claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000004056 anthraquinones Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 description 25
- -1 heptamethylene group Chemical group 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000004040 coloring Methods 0.000 description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 230000003595 spectral effect Effects 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZINRVIQBCHAZMM-UHFFFAOYSA-N 1-Amino-2,4-dibromoanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC(Br)=C2N ZINRVIQBCHAZMM-UHFFFAOYSA-N 0.000 description 1
- FJJMTRXALHEJFS-UHFFFAOYSA-N 2,4-dibromo-1-(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC(Br)=C2NC FJJMTRXALHEJFS-UHFFFAOYSA-N 0.000 description 1
- 125000004813 2-ethylethylene group Chemical group [H]C([H])([H])C([H])([H])C([H])([*:2])C([H])([H])[*:1] 0.000 description 1
- 125000004807 2-methylethylene group Chemical group [H]C([H])([H])C([H])([*:2])C([H])([H])[*:1] 0.000 description 1
- JDIOBXDRZVLCFV-UHFFFAOYSA-N 2-oxopyran-3-carbaldehyde Chemical compound O=CC1=CC=COC1=O JDIOBXDRZVLCFV-UHFFFAOYSA-N 0.000 description 1
- JNRLEMMIVRBKJE-UHFFFAOYSA-N 4,4'-Methylenebis(N,N-dimethylaniline) Chemical compound C1=CC(N(C)C)=CC=C1CC1=CC=C(N(C)C)C=C1 JNRLEMMIVRBKJE-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000004696 Poly ether ether ketone Substances 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical group CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 238000000411 transmission spectrum Methods 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Optical Filters (AREA)
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は、光学カラーフィルター用の青色色素に関す
る。TECHNICAL FIELD The present invention relates to a blue dye for optical color filters.
（従来の技術） 現在、フィルターの多くはゼラチン類を基材としている
ため、耐久性が充分でなかった。そこで基材として、耐
久性の良好な樹脂または無機の透明な物質の利用が検討
されている（特開昭59-127036）。(Prior Art) Currently, many filters have gelatin as a base material, and thus have insufficient durability. Therefore, use of a resin having good durability or an inorganic transparent substance as a substrate has been studied (Japanese Patent Laid-Open No. 59-127036).
（発明が解決しようとする問題点） 樹脂または無機物質の透明着色材としては、油溶性染料
または分散染料が知られている（染料便覧、丸善刊）。(Problems to be Solved by the Invention) As a transparent coloring material of a resin or an inorganic substance, an oil-soluble dye or a disperse dye is known (Dye Handbook, published by Maruzen).
しかし、これらの色素の中では、充分な着色性、耐久性
（特に耐光、耐熱性）を有し、かつ分光特性に優れた色
素がなかった。However, among these dyes, no dye has sufficient coloring properties and durability (particularly light resistance and heat resistance) and has excellent spectral characteristics.
又、新しいフィルターの製造方法として検討されている
昇華蒸着法（特開昭59-127036など）の方法に適する色
素もなかった。Further, there is no dye suitable for the sublimation vapor deposition method (Japanese Patent Laid-Open No. 59-127036, etc.) which is being investigated as a method for producing a new filter.
（問題点を解決するための手段） 本発明者らは、上記目的に適した色素について、鋭意検
討の結果、耐光、耐熱性のよい色素を見出し、本発明を
完成した。(Means for Solving Problems) The inventors of the present invention have conducted intensive studies on dyes suitable for the above purposes, and have found a dye having good light resistance and heat resistance, and completed the present invention.
即ち、本発明は一般式（Ｉ） （式中、Ｒは、水素原子またはアルキル基を示し、-X-
は-O-または-S-を示し、-A-は直鎖状もしくは分岐鎖状
のアルキレン基、アルキレン-O-アルキレン基、アルキ
レン-S-アルキレン基、-CH2CH(OH)-CH2-、 を示す。）で表わされるフィルター用青色色素に関す
る。That is, the invention has the general formula (I) (In the formula, R represents a hydrogen atom or an alkyl group, and -X-
Represents -O- or -S-, and -A- represents a linear or branched alkylene group, alkylene-O-alkylene group, alkylene-S-alkylene group, -CH 2 CH (OH) -CH 2 -, Indicates. ) Relates to a blue dye for a filter.
本発明の色素は、前記一般式（Ｉ）で表わされるもので
あり、式中のＲで表わされるアルキル基としては、炭素
数１〜20の直鎖もしくは分岐のアルキル基を意味する。The dye of the present invention is represented by the general formula (I), and the alkyl group represented by R in the formula means a linear or branched alkyl group having 1 to 20 carbon atoms.
また、-A-としてはつぎが挙げられる。すなわち、炭素
数１〜８の直鎖状または分岐鎖状のアルキレン基、具体
的にはメチレン基材、エチレン基、トリメチレン基、テ
トラメチレン基、ペンタメチレン基、ヘキサメチレン
基、ヘプタメチレン基、オクタメチレン基、2-メチルエ
チレン基、2-エチルエチレン基、2-メチルトリメチレン
基、2-ヒドロキシトリメチレン基、3-メチルトリメチレ
ン基、2,2-ジメチルトリメチレン基、2-エチル-2-メチ
ルトリメチレン基、2-メチル-2-プロピルトリメチレン
基、2-ブチル-2-メチルトリメチレン基、2,2-ジエチル
トリメチレン基、2-ブチル-2-エチルトリメチレン基、2
-メチルテトラメチレン基、2-メチルペンタメチレン
基、3-メチルペンタメチレン基、3-エチル-3-メチルペ
ンタメチレン基、3,3-ジメチルペンタメチレン基、2-メ
チルヘキサメチレン基、2-メチルヘプタメチレン基、４
−メチルヘプタメチレン基、シクロヘキシレン基、フェ
ニレン基等の基が挙げられる。The following are examples of -A-. That is, a linear or branched alkylene group having 1 to 8 carbon atoms, specifically, a methylene base material, ethylene group, trimethylene group, tetramethylene group, pentamethylene group, hexamethylene group, heptamethylene group, octane group. Methylene group, 2-methylethylene group, 2-ethylethylene group, 2-methyltrimethylene group, 2-hydroxytrimethylene group, 3-methyltrimethylene group, 2,2-dimethyltrimethylene group, 2-ethyl-2 -Methyltrimethylene group, 2-methyl-2-propyltrimethylene group, 2-butyl-2-methyltrimethylene group, 2,2-diethyltrimethylene group, 2-butyl-2-ethyltrimethylene group, 2
-Methyltetramethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group, 3-ethyl-3-methylpentamethylene group, 3,3-dimethylpentamethylene group, 2-methylhexamethylene group, 2-methyl Heptamethylene group, 4
Examples include groups such as a methylheptamethylene group, a cyclohexylene group, and a phenylene group.
本発明の色素は、公知の方法により、下記式の化合物と シクロヘキシルアミンを反応させたのち、アルコールま
たはチオアルコール類と反応させることにより得られ
る。The dye of the present invention, by a known method, a compound of the following formula It is obtained by reacting cyclohexylamine and then reacting with alcohol or thioalcohol.
このような方法により得られる本発明の色素としては、
表-1に示すような色素があげられる。The dye of the present invention obtained by such a method,
The dyes shown in Table 1 are listed.
表-1に本発明の色素とフイルターとしての性能を示し
た。Table 1 shows the dyes of the present invention and their performance as filters.
表-1において、性能試験および評価はつぎの通りであ
る。 In Table-1, the performance tests and evaluations are as follows.
1)着色性 PET（ポリエチレンテレフタレート）：フィルムと色素
原体とエチレングリコールを入れ130℃にて１時間染色
した時の着色性 PS（ポリスチレン）：樹脂と色素を混合し成型した時の
着色性 Al：アルミナゲルをガラスに塗布、焼成して得た基材
（γ−アルミナ）に色素を転写した時の着色性 2)耐熱性 着色をした各基材(PET、PS、Al)での大気中180℃で４時
間加熱後の透過スペクトル変化量が 変化なし ◎ 10％以下 ○ 30％以内 △ 30％以上 × 3)耐光性 着色をした各基材(PET、PS、Al)のフエードメーター20
時間後のスペクトル変化量が 変化なし ◎ 10％以下 ○ 30％以内 △ 30％以上 × 4)昇華性 大気圧下、200℃以下で昇華する時を○、昇華しない時
を×とした。1) Colorability PET (polyethylene terephthalate): Colorability when a film, a dye base and ethylene glycol are put and dyed at 130 ° C for 1 hour PS (polystyrene): Colorability when a resin and a dye are mixed and molded Al : Coloring properties when dyes are transferred to a substrate (γ-alumina) obtained by coating and firing alumina gel on glass 2) Heat resistance In the atmosphere with each colored substrate (PET, PS, Al) No change in transmission spectrum change after heating at 180 ℃ for 4 hours ◎ 10% or less ○ Within 30% △ 30% or more × 3) Light resistance Fade meter of each colored substrate (PET, PS, Al) 20
No change in spectrum after time ◎ 10% or less ○ Within 30% △ 30% or more × 4) Sublimation property At atmospheric pressure, when sublimation occurs at 200 ° C or less, it is indicated as ○, and when it does not sublimate, it is indicated as ×.
5)フィルター性能 540nmの透過率が５％以下となる様な濃度で着色した基
材の460nmの透過率が 55％以上 ○ 、55％未満 × 本発明の色素を用いて、着色する基材としては熱可塑性
樹脂（ポリスチレン、ポリエチレン、ポリプロピレン、
アクリル樹脂、ＡＢＳ樹脂、ポリアセタール、ポリカー
ボネートなど）、熱硬化性樹脂（アミノ樹脂、フェノー
ル樹脂、ポリウレタン、ポリエステル。ポリエーテルス
ルホン、ポリエーテルエーテルケトンなど）、アルミナ
膜（ガラスまたは樹脂に保持）、シリカ膜（ガラスまた
は樹脂に保持）などが挙げられ、その着色方法は煉り込
み、転写、染色、昇華蒸着などがある。5) Filter performance: The substrate colored at a concentration such that the transmittance at 540 nm is 5% or less has a transmittance at 460 nm of 55% or more. ○, less than 55% × As a substrate to be colored using the dye of the present invention Is a thermoplastic resin (polystyrene, polyethylene, polypropylene,
Acrylic resin, ABS resin, polyacetal, polycarbonate, etc., thermosetting resin (amino resin, phenol resin, polyurethane, polyester, polyether sulfone, polyether ether ketone, etc.), alumina film (retained on glass or resin), silica film (Holding on glass or resin) and the like, and coloring methods thereof include bricking, transfer, dyeing, and sublimation deposition.
（作用及び効果） 従来のフィルターは耐久性、着色性等に問題があった
が、本発明のフィルターは着色性、耐熱性、耐光性、昇
華性にすぐれ、更に分光特性にも優れた実用上極めて有
用な色素である。(Operation and effect) The conventional filter had problems in durability, coloring property, etc., but the filter of the present invention is excellent in coloring property, heat resistance, light resistance, sublimation property, and practically excellent in spectral characteristics. It is a very useful dye.
（実施例） 以下、実施例により本発明を詳しく説明する。(Examples) Hereinafter, the present invention will be described in detail with reference to Examples.
ただし、「部」は重量部を表す。However, "parts" represent parts by weight.
実施例−１ スルホラン50部、酢酸カリ3.4部、臭化銅0.1部、1-アミ
ノ-2,4-ジブロムアントラキノン10部、シクロヘキシル
アミン3.0部を混合し、150℃で５時間加熱攪拌したの
ち、メタノール排出より取り出した。Example-1 50 parts of sulfolane, 3.4 parts of potassium acetate, 0.1 part of copper bromide, 10 parts of 1-amino-2,4-dibromoanthraquinone, and 3.0 parts of cyclohexylamine were mixed, and after heating and stirring at 150 ° C. for 5 hours. , Methanol was taken out.
下記構造式 で示されるアントラキノン系化合物10部、スルホラン75
部、炭酸カリ3.3部、メルカプトエタノール４部を混合
し、50℃で１時間加熱撹拌した。室温まで放置冷却後、
メタノール水に排出し、析出した固体を濾別し、カラム
精製にて下記色素４部を得た。The following structural formula 10 parts of anthraquinone compound represented by, sulfolane 75
Parts, potassium carbonate 3.3 parts, and mercaptoethanol 4 parts were mixed, and the mixture was heated with stirring at 50 ° C. for 1 hour. After cooling to room temperature,
It was discharged into methanol water, the precipitated solid was filtered off, and 4 parts of the following dye was obtained by column purification.
λmax（クロロホルム中） 632nm 元素分析 この色素10部を、ポリプロピレングリコール100部と混
合し、微粒子化後、紙に塗布、乾燥し転写紙をつくり、
アルミナゲルを塗布、焼成した厚さ3mmガラス板に200℃
にて転写し、青色フィルターをつくった。このフィルタ
ーの分光特性（透過性）を分光光度計で測定したチヤー
トを図-1に示す。 λmax (in chloroform) 632nm Elemental analysis 10 parts of this dye is mixed with 100 parts of polypropylene glycol, and after being made into fine particles, coated on paper and dried to make a transfer paper,
200 ℃ on a 3mm thick glass plate coated with alumina gel and baked.
, And made a blue filter. Figure 1 shows the chart obtained by measuring the spectral characteristics (transmittance) of this filter with a spectrophotometer.
実施例−２ スルホラン50部、酢酸カリ3.4部、臭化銅0.1部、1-メチ
ルアミノ-2,4-ジブロムアントラキノン10部、シクロヘ
キシルアミン3.0部を混合し、150℃で５時間加熱撹拌し
たのち、メタノール排出より取り出した下記構造式 で示されるアントラキノン系化合物10部、苛性カリ２
部、エチレングリコール50部を混合し、130℃で３時間
加熱撹拌した。室温まで放置冷却後、70％メタノールに
排出し、析出した固体を濾別し、カラム精製にて下記色
素4.5部を得た。Example-2 50 parts of sulfolane, 3.4 parts of potassium acetate, 0.1 part of copper bromide, 10 parts of 1-methylamino-2,4-dibromoanthraquinone, and 3.0 parts of cyclohexylamine were mixed and heated and stirred at 150 ° C. for 5 hours. After that, the following structural formula taken from the methanol discharge 10 parts of anthraquinone compound represented by, caustic potash 2
And 50 parts of ethylene glycol were mixed and heated and stirred at 130 ° C. for 3 hours. After cooling to room temperature, it was discharged into 70% methanol, the precipitated solid was separated by filtration, and 4.5 parts of the following dye was obtained by column purification.
λmax（クロロホルム中） 610nm 元素分析 ポリエステルフイルム10部、エチレングリコール2000部
と得られた色素２部を入れ、130℃１時間で染色し、青
色フイルターをつくった。 λmax (in chloroform) 610nm Elemental analysis 10 parts of polyester film, 2000 parts of ethylene glycol and 2 parts of the obtained dye were added and dyed at 130 ° C. for 1 hour to prepare a blue filter.
このフィルターの分光特性（透過率）を分光光度計で測
定したチヤートを図-2に示す。Figure 2 shows the chart obtained by measuring the spectral characteristics (transmittance) of this filter with a spectrophotometer.
実施例−３ 実施例１及び２と同様の方法で合成した下記構造式で示
されるアントラキノン系化合物 10部、苛性カリ２部、ハイドロキノン10部、スルホラン
50部を混合し、130℃で４時間加熱撹拌した。室温まで
放置冷却後、70％メタノールに排出し、析出した固体を
濾別し、カラム精製にて下記色素5.1部を得た。Example-3 Anthraquinone compound represented by the following structural formula synthesized by the same method as in Examples 1 and 2 10 parts, caustic potash 2 parts, hydroquinone 10 parts, sulfolane
50 parts were mixed and heated and stirred at 130 ° C. for 4 hours. After cooling to room temperature, it was discharged into 70% methanol, the precipitated solid was separated by filtration, and 5.1 parts of the following dye was obtained by column purification.
λmax（クロロホルム中） 612nm 元素分析 ポリメチルメタアクリレート樹脂板に、得られた色素１
部とパイロナールＭＤ−1200（東洋紡績社製品）10部と
シリカゲル１部より調製、作製した転写紙（フィルター
用に色素を配置）をのせ、200℃でカレンダーを通した
ところ、青色のフィルターが得られた。 λmax (in chloroform) 612nm Elemental analysis Dye 1 obtained on a polymethylmethacrylate resin plate
Part, Pyronal MD-1200 (product of Toyobo Co., Ltd.) and 1 part of silica gel, transfer paper prepared (prepared with dyes for filters) was placed on it and passed through a calendar at 200 ° C to obtain a blue filter. Was given.
このフィルターの分光特性（透過率）を分光光度計で測
定したチヤートを図-3に示す。Figure 3 shows the chart obtained by measuring the spectral characteristics (transmittance) of this filter with a spectrophotometer.
図-1、-2、及び図-3は本発明に係る色素を用いて、実施
例-1、-2、及び実施例-3にて作製したフィルターの各波
長での分光光度計での透過率を示す図である。FIGS. -1, -2, and -3 are transmissions in the spectrophotometer at each wavelength of the filters prepared in Examples -1, -2, and Example -3, using the dye according to the present invention. It is a figure which shows a rate.
Claims (1)
は−Ｏ−または−Ｓ−を示し、−Ａ−は直鎖状もしくは
分岐鎖状のアルキレン基、−ＣＨ２ＣＨ（ＯＨ）ＣＨ２
−、 を示す。ただし、Ｒが水素原子の時は−Ｘ−は−Ｓ−を
示し、Ｒがアルキル基の時は−Ｘ−は−Ｏ−を示す〕で
表されるアントラキノン系フィルター用青色色素。1. A general formula (I) [In the formula, R represents a hydrogen atom or an alkyl group, and -X-
It represents -O- or -S-, -A- is a linear or branched alkylene group, -CH 2 CH (OH) CH 2
-, Indicates. However, when R is a hydrogen atom, -X- represents -S-, and when R is an alkyl group, -X- represents -O-.], A blue dye for anthraquinone filters.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28674986A JPH0657798B2 (en) | 1986-12-03 | 1986-12-03 | Blue dye for filters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28674986A JPH0657798B2 (en) | 1986-12-03 | 1986-12-03 | Blue dye for filters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63139948A JPS63139948A (en) | 1988-06-11 |
| JPH0657798B2 true JPH0657798B2 (en) | 1994-08-03 |
Family
ID=17708537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28674986A Expired - Lifetime JPH0657798B2 (en) | 1986-12-03 | 1986-12-03 | Blue dye for filters |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0657798B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2476886C (en) * | 2002-03-22 | 2011-02-15 | Ciba Specialty Chemicals Holding Inc. | Anthraquinone dyes |
| JP4500053B2 (en) * | 2002-03-22 | 2010-07-14 | チバ ホールディング インコーポレーテッド | Anthraquinone dye |
| CN106997068B (en) * | 2017-04-26 | 2023-03-28 | 杭州科汀光学技术有限公司 | Infrared-isolating filter using glass with blue ink dipped as substrate and preparation method thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH635123A5 (en) * | 1978-04-21 | 1983-03-15 | Ciba Geigy Ag | MIXTURE OF 6/7 HALOGEN ANTHRACHINONE COMPOUNDS AND THEIR PRODUCTION. |
-
1986
- 1986-12-03 JP JP28674986A patent/JPH0657798B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63139948A (en) | 1988-06-11 |
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