JPS63225667A - Novel monoazo lake pigment - Google Patents
Novel monoazo lake pigmentInfo
- Publication number
- JPS63225667A JPS63225667A JP62058869A JP5886987A JPS63225667A JP S63225667 A JPS63225667 A JP S63225667A JP 62058869 A JP62058869 A JP 62058869A JP 5886987 A JP5886987 A JP 5886987A JP S63225667 A JPS63225667 A JP S63225667A
- Authority
- JP
- Japan
- Prior art keywords
- diffraction
- pigment
- formula
- parts
- diffraction intensity
- 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.)
- Granted
Links
- 239000000049 pigment Substances 0.000 title claims abstract description 43
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims abstract description 21
- 238000002441 X-ray diffraction Methods 0.000 claims abstract description 10
- 238000010586 diagram Methods 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 14
- 239000003973 paint Substances 0.000 abstract description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 9
- 239000000203 mixture Substances 0.000 abstract description 8
- 239000000725 suspension Substances 0.000 abstract description 8
- 239000013078 crystal Substances 0.000 abstract description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 2
- 150000001412 amines Chemical class 0.000 abstract description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000000976 ink Substances 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000004040 coloring Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 5
- 238000005755 formation reaction Methods 0.000 description 5
- 159000000009 barium salts Chemical class 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- 229920000180 alkyd Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 229910002483 Cu Ka Inorganic materials 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 238000006149 azo coupling reaction Methods 0.000 description 2
- ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 2
- IWOUKMZUPDVPGQ-UHFFFAOYSA-N barium nitrate Chemical compound [Ba+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O IWOUKMZUPDVPGQ-UHFFFAOYSA-N 0.000 description 2
- MPHCLXFWCXFAFC-UHFFFAOYSA-L barium(2+);dichloride;hydrate Chemical compound O.[Cl-].[Cl-].[Ba+2] MPHCLXFWCXFAFC-UHFFFAOYSA-L 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- -1 polyethylene Polymers 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 229910017488 Cu K Inorganic materials 0.000 description 1
- 229910017541 Cu-K Inorganic materials 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000011981 development test Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 229920006284 nylon film Polymers 0.000 description 1
- 229940104573 pigment red 5 Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
- C09B67/0015—Influencing the physical properties by treatment with a liquid, e.g. solvents of azoic pigments
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0025—Crystal modifications; Special X-ray patterns
- C09B67/0028—Crystal modifications; Special X-ray patterns of azo compounds
- C09B67/0029—Crystal modifications; Special X-ray patterns of azo compounds of monoazo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は、鮮明性、着色力、光沢、耐水性、耐熱性等に
優れ、印刷インキ、塗料、グラスチック、文具用等に賞
月される赤色系新規モノアゾレーキ顔料に関するもので
ある。[Detailed Description of the Invention] <Industrial Application Field> The present invention has excellent clarity, coloring power, gloss, water resistance, heat resistance, etc., and has been praised for use in printing inks, paints, glass sticks, stationery, etc. This invention relates to a new red monoazo lake pigment.
〈従来の技術及びその問題点〉
従来、式（Ｉ）
で示されるモノアゾレーキ顔料は、例えば式（ＩＩ）で
示されるアミンを５℃以下でジアゾ化して得たジアゾ成
分と、式（ＩＩＩ）
で示される酸を苛性ソーダ水溶液に溶解して得たカフプ
ラー成分とを、５℃以下でカップリング反応させて得ら
れた式（Ｉ’Ｖ）
で示されるモノアゾ染料の懸濁液にバリウム塩の水溶液
を加え、５℃以下で反応させてレーキ化することにより
得られていた。<Prior art and its problems> Conventionally, monoazo lake pigments represented by the formula (I) have been produced by combining a diazo component obtained by diazotizing an amine represented by the formula (II) at 5°C or lower, and a diazo component represented by the formula (III). An aqueous solution of a barium salt was added to a suspension of a monoazo dye represented by formula (I'V) obtained by a coupling reaction at 5° C. or below with a cuff puller component obtained by dissolving the acid shown in an aqueous solution of caustic soda. In addition, it was obtained by reacting at 5° C. or lower to form a lake.
こうして得られた式（Ｉ）で示される従来のモノアゾレ
ーキ顔料は、Ｘ線回折図において回折角度（２θ±０．
２°： Ｃｕ −Ｋａ ） ４．９°に強い回折強度を
有し、２６．２°に中程度の回折強度を有し、１４．８
°に比較的弱い回折強度を有している。The conventional monoazo lake pigment represented by the formula (I) thus obtained has a diffraction angle (2θ±0.
2°: Cu-Ka) has strong diffraction intensity at 4.9°, moderate diffraction intensity at 26.2°, and 14.8°
It has a relatively weak diffraction intensity at °.
しかし、上記のＸ線回折パターンを有する結晶型（以下
、α型と称す）のモノアゾレーキ顔料は、現在上布され
ているＣ、１．ピグメントレッド５７：１で知られるカ
ルシウムレーキ顔料に比べ耐水性は良好であるが、印刷
インキや塗料にした場合、鮮明性、着色力、光沢が劣シ
、プラスチックの着色に用いた場合、耐熱性に劣るため
、実際１ｃ顔料として上布されるＫは至っていない。However, the crystal type (hereinafter referred to as α type) monoazo lake pigment having the above-mentioned X-ray diffraction pattern is currently available in C, 1. It has better water resistance than the calcium lake pigment known as Pigment Red 57:1, but when used in printing inks and paints, it has poor clarity, coloring power, and gloss, and when used to color plastics, it has poor heat resistance. In fact, K has not been used as a 1c pigment on textiles because of its inferiority.
く問題点を解決するための手段〉
本発明者等は、かかる難点を解消するため、式で示され
るモノアゾ染料の顔料化法について鋭意検討した結果、
当該染料を加熱した後、レーキ化すると、従来のα型顔
料とはＸ線回折ノ４ターンを異にする、鮮明性、着色力
、光沢、耐水性、耐熱性等に優れた新しい結晶型の顔料
が得られる事を見い出し、本発明を完成するに至った。Means for Solving the Problems> In order to solve the problems, the inventors of the present invention have conducted intensive studies on the method of converting the monoazo dye represented by the formula into a pigment, and have found that:
When the dye is heated and turned into a lake, a new crystal type with excellent clarity, coloring power, gloss, water resistance, heat resistance, etc., which differs from conventional α-type pigments in four turns of X-ray diffraction, is created. They discovered that pigments can be obtained and completed the present invention.
即ち、本発明は、Ｘ線回折図において回折角度（２θ±
０．２°； Ｃｕ −Ｋａ） ５．０’に強い回折強度
を有し、１４．８°、２４．７°、２５．３°に中程度
の回折強度を有し、９．８°、１１．１°、１８．３°
、１９．３°、２６．６°。That is, the present invention provides diffraction angles (2θ±
0.2°; Cu-Ka) has strong diffraction intensity at 5.0', moderate diffraction intensity at 14.8°, 24.7°, 25.3°, 9.8°, 11.1°, 18.3°
, 19.3°, 26.6°.
２７．４°に比較的弱い回折強度を有することを特徴と
する式（Ｉ）
で示される新規モノアゾレーキ顔料に関するものである
。This invention relates to a novel monoazo lake pigment represented by formula (I), which is characterized by having a relatively weak diffraction intensity at 27.4°.
本発明のモノアゾレーキ顔料は、上記した様に従来のα
型顔料とは全く異なるＸ線回折・母ターンを有する結晶
型（以下、ｒ型と称す）の顔料であシ、例えば従来と同
様にして得た式（■）で示されるモノアゾ染料の懸濁液
を、４６〜７０℃、好ましくは５０〜７０℃に加熱した
後、バリウム塩の水溶液を加え、通常７０℃以下で反応
させてレーキ化することによシ得られる。なかでも鮮明
性、着色力、光沢等に優れるｒ型顔料が収率よく得られ
る点で、該染料の懸濁液を加熱して５５〜６５℃に２〜
２０分間保持した後、バリウム塩の水溶液を加え、０〜
６５℃で反゛応させてレーキ化する方法が特に好ましい
。As mentioned above, the monoazo lake pigment of the present invention has a conventional α
It is a crystal-type pigment (hereinafter referred to as r-type) that has an X-ray diffraction pattern and mother turn that are completely different from type pigments, for example, a suspension of a monoazo dye represented by the formula (■) obtained in the same manner as before. After heating the liquid to 46 to 70°C, preferably 50 to 70°C, an aqueous solution of barium salt is added, and the mixture is reacted at usually 70°C or lower to form a lake. Among them, R-type pigments with excellent clarity, coloring power, gloss, etc. can be obtained in high yield, and a suspension of the dye is heated to 55-65°C for 2 to 65°C.
After holding for 20 minutes, add an aqueous solution of barium salt and
Particularly preferred is a method of reacting at 65°C to form a lake.
本発明で使用されるレーキ化用のバリウム塩としては、
例えば塩化バリウム、硝酸バリウム、酢酸バリウム等を
挙げることができる。The barium salt for lake formation used in the present invention includes:
Examples include barium chloride, barium nitrate, barium acetate, and the like.
〈発明の効果〉
本発明に係る新規なｒ型の赤色系モノアゾレーキ顔料は
、印刷インキや塗料等に使用した場合、非常に鮮明で着
色力、光沢、耐水性に優れ、更にグラスチックの着色に
使用した場合、耐熱性に優れるものである。<Effects of the Invention> The new r-type red monoazo lake pigment of the present invention is very clear and has excellent coloring power, gloss, and water resistance when used in printing inks, paints, etc., and is also suitable for coloring glass materials. When used, it has excellent heat resistance.
〈実施例〉
以下に実施例、比較例及び試験例を挙げ、本発明を更に
詳細に説明するが、本発明はこれＫより限定されるもの
ではない。尚、型中の部及びチは重量基準である。<Example> The present invention will be explained in more detail by referring to Examples, Comparative Examples, and Test Examples below, but the present invention is not limited thereto. Note that the parts and parts in the mold are based on weight.
実施例１
２−−ｒミノ−５−メチルベンゼンスルホン酸２０．０
部を水２００部に分散後、２０％塩酸２２．０部を加え
、０℃に保ちながら３０％亜硝酸ソーダ水溶液２５．１
部を滴下し、ジアゾ化してジアゾ液を得た。Example 1 2-rmino-5-methylbenzenesulfonic acid 20.0
After dispersing 1 part in 200 parts of water, 22.0 parts of 20% hydrochloric acid was added, and 25.1 parts of a 30% sodium nitrite aqueous solution was added while maintaining the temperature at 0°C.
was added dropwise to diazotize the mixture to obtain a diazo liquid.
次に２−ヒドロキシ−３−ナフトエ酸２０．６部を６０
℃で水２４２部に分散後、４８％苛性ソーダ水溶液２２
．０部を加えて溶解してカッグラ−溶液を得た。このカ
ップラー溶液を０℃に冷却し、攪拌しながら上記ジアゾ
液を滴下し、０℃で６０分間攪拌してカップリング反応
を終了させた後、１０％口ジンソーダ水溶液６０部を加
え、６０分間攪拌してモノアゾ染料の懸濁液を得た。Next, 20.6 parts of 2-hydroxy-3-naphthoic acid was added to 60 parts of 2-hydroxy-3-naphthoic acid.
After dispersing in 242 parts of water at ℃, 22 parts of 48% caustic soda aqueous solution
．． 0 parts were added and dissolved to obtain a Kaglar solution. This coupler solution was cooled to 0°C, and the above diazo solution was added dropwise while stirring. After stirring at 0°C for 60 minutes to complete the coupling reaction, 60 parts of a 10% gin-soda aqueous solution was added and stirred for 60 minutes. A suspension of monoazo dye was obtained.
この染料懸濁液を２９分間かけて５７℃まで加熱した後
、同温度に１０分間保持し、次いで塩化バリウム水和物
３８．６部を水１５０部に溶解した液を加え、５７℃に
て１０分間攪拌後、−を７．６に調整し、更に６０分間
攪拌してレーキ化反応を終了した。レーキ化反応終了後
、８０℃で６０分間加熱攪拌してから熱時ｐ遇し水洗後
、８０℃で乾燥して黄味赤色のモノアゾレーキ顔料粉末
５８．７部を得た。This dye suspension was heated to 57°C over 29 minutes, kept at the same temperature for 10 minutes, then a solution of 38.6 parts of barium chloride hydrate dissolved in 150 parts of water was added, and the mixture was heated at 57°C. After stirring for 10 minutes, - was adjusted to 7.6, and the mixture was further stirred for 60 minutes to complete the lake formation reaction. After completion of the lake formation reaction, the mixture was heated and stirred at 80° C. for 60 minutes, heated, washed with water, and dried at 80° C. to obtain 58.7 parts of yellowish red monoazo lake pigment powder.
この顔料は、第１図に示す様に、Ｘ線回折図において回
折角度（２θ±０．２°：Ｃｕ−にα）５．０°に強い
回折強度を有し、１４．８°、２４．７°、２５．３°
に中程度の回折強度を有し、９．８°、 １１．１’、
１８．３°。As shown in Figure 1, this pigment has a strong diffraction intensity at a diffraction angle of 5.0° (2θ±0.2°: α for Cu-), 14.8°, 24 .7°, 25.3°
It has a moderate diffraction intensity at 9.8°, 11.1',
18.3°.
１９．３°、２６．６°、２７．４°に比較的弱い回折
強度を有していた。尚、第３図にこの顔料の赤外線吸収
スペクトルを示す。It had relatively weak diffraction intensities at 19.3°, 26.6°, and 27.4°. Incidentally, FIG. 3 shows the infrared absorption spectrum of this pigment.
実施例２
実施例１と同様にジアゾカップリング反応を行って得ら
れた染料懸濁液を３２分間かけて６３℃まで加熱した後
、同温度に１５分間保持し、次いで再びＩＯＣまで冷却
した後、酢酸バリウム４３．２部を水２００部に溶解し
た液を加え、１０℃にて６０分間攪拌後、−を７．６に
調整し、更に６０分間攪拌してレーキ化反応を終了した
以外は実施例１と同様にして、黄味赤色のモノアゾレー
キ顔料粉末５９．０部を得た。Example 2 A dye suspension obtained by performing a diazo coupling reaction in the same manner as in Example 1 was heated to 63°C over 32 minutes, held at the same temperature for 15 minutes, and then cooled again to IOC. , except that a solution of 43.2 parts of barium acetate dissolved in 200 parts of water was added, and after stirring at 10°C for 60 minutes, - was adjusted to 7.6, and the lake formation reaction was completed by stirring for an additional 60 minutes. In the same manner as in Example 1, 59.0 parts of yellowish red monoazo lake pigment powder was obtained.
この顔料は、Ｘ線回折図において、実施例１の場合と同
様の回折角度にほぼ同様の回折強度を有していた。This pigment had almost the same diffraction intensity at the same diffraction angle as in Example 1 in the X-ray diffraction diagram.
比較例１
実施例１と同様にジアゾカップリング反応を行って得ら
れた染料懸濁液を加熱することなく用い、これに塩化バ
リウム水和物３８．６部を水１５０部に溶解した液を加
え、０℃にて６０分間攪拌した後、声を７．６１７Ｃｖ
Ｉ４整し、更に６０分間攪拌してレーキ化反応を終了し
た以外は実施例１と同様にして黄味赤色のモノアゾレー
キ顔料粉末６１．１部を得た。Comparative Example 1 A dye suspension obtained by carrying out a diazo coupling reaction in the same manner as in Example 1 was used without heating, and a solution obtained by dissolving 38.6 parts of barium chloride hydrate in 150 parts of water was added to it. After stirring at 0℃ for 60 minutes, the temperature was reduced to 7.617Cv.
61.1 parts of a yellowish red monoazo lake pigment powder was obtained in the same manner as in Example 1, except that the mixture was adjusted to I4 and the lake formation reaction was completed by further stirring for 60 minutes.
この顔料は、第２図に示す様に、Ｘ線回折図において回
折角度（２θ±０．２°：Ｃｕ−Ｋ（ｙ）４．９°に強
い回折強度を有し、２６．２°に中程度の回折強度を有
し、１４．８°に比較的弱い回折強度を有していた。尚
、第４図にこの顔料の赤外線吸収スペクトルを示す。As shown in Figure 2, this pigment has a strong diffraction intensity at a diffraction angle of 4.9° (2θ±0.2°: Cu-K(y)) and at 26.2° in an X-ray diffraction diagram. It had a medium diffraction intensity and a relatively weak diffraction intensity at 14.8°.The infrared absorption spectrum of this pigment is shown in Fig. 4.
試験例１（平版インキ展色試験）
実施例１〜２又は比較例１で得られた顔料４．０部とイ
ンキフェス１６．０部をツーパ一式マラーにて１００回
転で３回線肉してインキを調製し、こ ゛れを小型輪転
印刷機（Ｒ１テスター）を用いてアート紙に展色し、得
られた展色紙の彩度（４０勺を分光光度計によシ、光沢
（６０°）を光沢計によシ、濃度をブレタグ濃度計（反
射濃度計）によりそれぞれ測定した。その結果を第１表
に示す。Test Example 1 (Lithographic ink color development test) 4.0 parts of the pigment obtained in Examples 1 to 2 or Comparative Example 1 and 16.0 parts of the ink face were mixed 3 times at 100 revolutions with a two-piece muller to form an ink. The color saturation (40 mm) of the resulting colored paper was measured using a spectrophotometer, and the gloss (60°) was measured using a small rotary printing press (R1 tester). was measured using a gloss meter, and the density was measured using a Bretag densitometer (reflection densitometer).The results are shown in Table 1.
第 １ 表
実施例１〜２の顔料を用いたインキは、彩度が高く、光
沢良好、濃度大であった。Table 1 Inks using the pigments of Examples 1 and 2 had high chroma, good gloss, and high density.
試験例２（塗料試験）
実施例１〜２又は比較例１で得られた顔料１２部、メラ
ミンアルキッド樹脂（メラミン樹脂とアルキッド樹脂の
重量比＝３ニア）５２部、キシレン５２部及びガラスピ
ーズ１２０部をポリエチレン製ピンに入れ、ペイントコ
ンディショナーで１時間分散した後、上記メラミンアル
キッド樹脂５０部を追加して、更に１０分間ペイントコ
ンディショナーで分散し、ガラスピーズを戸別して赤色
塗料を得た。次いでこの塗料を塗装板に吹き付けて焼き
付けた後、塗膜の光沢（６０°）を光沢針によシ測定し
た。その結果を第２表に示す。Test Example 2 (Paint Test) 12 parts of the pigment obtained in Examples 1 to 2 or Comparative Example 1, 52 parts of melamine alkyd resin (weight ratio of melamine resin and alkyd resin = 3 nia), 52 parts of xylene, and 120 parts of glass beads After dispersing in a paint conditioner for 1 hour, 50 parts of the above melamine alkyd resin was added and further dispersed in a paint conditioner for 10 minutes, and the glass beads were distributed from house to house to obtain a red paint. Next, this paint was sprayed onto a painted board and baked, and the gloss (60°) of the paint film was measured using a gloss needle. The results are shown in Table 2.
第２表
実施例１〜２の顔料を用いた塗料は、光沢良好であった
。The paints using the pigments of Examples 1 and 2 in Table 2 had good gloss.
試験例３（耐水性試験）
実施例１〜２あるいは比較例１で得られた顔料又は市販
のカルシウムレーキ顔料（Ｃ，１，ピグメントレッド５
７：１）１２部、ウレタン系樹脂８４部、メチルエチル
ケトン１２部及びスチールビーズ１５０部をポリエチレ
ン製ピンに入れ、（インドコンディショナーで１時間分
散した後、スチールピーズを戸別して赤色インキを得た
。この赤色インキを０．１５ｍバーコーダ−を用いてナ
イロン製フィルム上に展色した後、このフィルムの展色
面上にろ紙を重ね合せ、これを更に２枚のアルミニウム
板ではさんでクリップで止め、水中で１時間煮沸した後
、重ね合せてあったろ紙をはがして、ろ紙上への顔料の
マイグレーションの程ｉｔ−グレタグ濃度計で濃度を計
ることにより求めた。その結果を第３表に示す。Test Example 3 (Water Resistance Test) The pigment obtained in Examples 1 to 2 or Comparative Example 1 or the commercially available calcium lake pigment (C, 1, Pigment Red 5)
7:1), 84 parts of urethane resin, 12 parts of methyl ethyl ketone, and 150 parts of steel beads were placed in a polyethylene pin (after dispersing with India conditioner for 1 hour, the steel beads were sent door to door to obtain red ink. After spreading red ink on a nylon film using a 0.15m barcoder, a filter paper was placed on top of the color spreading surface of the film, which was further sandwiched between two aluminum plates, fixed with clips, and then placed under water. After boiling for 1 hour, the overlapping filter paper was peeled off, and the concentration of pigment migration onto the filter paper was measured using an IT-Gretag densitometer.The results are shown in Table 3.
第３表
実施例１〜２及び比較例１の顔料を用いたイン中は、Ｃ
，１，ピグメントレッド５７：１よシ耐水性が良好であ
った。In Table 3, in which the pigments of Examples 1 and 2 and Comparative Example 1 were used, C
, 1, Pigment Red 57:1 had better water resistance.
試験例４（耐熱性試験）
実施例１〜２又は比較例１で得られた顔料６部、ステア
リン酸亜鉛２部から成るドライカラーをポリプロピレン
１２００部とブレンドし、３オンスインラインスクリユ
一タイプ射出成形機を用い、成形温度２８０℃で滞留時
間０分と２０分の条件でそれぞれ平板を成形し、３つの
色差（ΔＥ）を測定し、耐熱性の評価を行った。その結
果を第４表に示す。Test Example 4 (Heat Resistance Test) A dry color consisting of 6 parts of the pigment obtained in Examples 1 to 2 or Comparative Example 1 and 2 parts of zinc stearate was blended with 1200 parts of polypropylene, and the mixture was injected using a 3-ounce in-line screw type. Using a molding machine, flat plates were molded at a molding temperature of 280° C. and a residence time of 0 minutes and 20 minutes, respectively, and three color differences (ΔE) were measured to evaluate heat resistance. The results are shown in Table 4.
第４表
実施例１〜２の顔料で着色された平板は、色差（ΔＥ）
が小さく、それぞれ鮮明な赤色を呈しており、耐熱性に
優れていた。Table 4 Flat plates colored with the pigments of Examples 1 and 2 have color difference (ΔE)
They were small in size, had a bright red color, and had excellent heat resistance.
第、１図は実施例１で得られた本発明のモノアゾレーキ
顔料（ｒ型）のＸ線回折図（２θ±０．２°：Ｃｕ−に
、）、第２図は比較例１で得られた従来のモノアゾレー
キ顔料（αを）のＸ線回折図（２θ±０．２°；Ｃｕ−
にα）であり、また第３図は実施例１で得られた本発明
のモノアゾレーキ顔料（ｒ型）の赤外線吸収スペクトル
図、第４図は比較例１で得られた従来のモノアゾレーキ
顔料（α型）の赤外線吸収スペクトル図である。1 is an X-ray diffraction diagram (2θ±0.2°: Cu-) of the monoazo lake pigment (r type) of the present invention obtained in Example 1, and FIG. The X-ray diffraction diagram of the conventional monoazo lake pigment (α) (2θ±0.2°; Cu-
3 is an infrared absorption spectrum diagram of the monoazo lake pigment (r type) of the present invention obtained in Example 1, and FIG. 4 is an infrared absorption spectrum diagram of the conventional monoazo lake pigment (α FIG. 2 is an infrared absorption spectrum diagram of the
Claims (1)
−Ｋ＿α）５．０°に強い回折強度を有し、１４．８°
、２４．７°、２５．３°に中程度の回折強度を有し、
９．８°、１１．１°、１８．３°、１９．３°、２６
．６°、２７．４°に比較的弱い回折強度を有すること
を特徴とする式（ I ） ▲数式、化学式、表等があります▼・・・（ I ） で示される新規モノアゾレーキ顔料。[Claims] In the X-ray diffraction diagram, the diffraction angle (2^θ±0.2°; Cu
-K_α) has strong diffraction intensity at 5.0° and 14.8°
, 24.7°, and 25.3° have moderate diffraction intensity,
9.8°, 11.1°, 18.3°, 19.3°, 26
．． A novel monoazo lake pigment represented by the formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I), which is characterized by having relatively weak diffraction intensities at 6° and 27.4°.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62058869A JPH083052B2 (en) | 1987-03-16 | 1987-03-16 | New monoazo lake pigment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62058869A JPH083052B2 (en) | 1987-03-16 | 1987-03-16 | New monoazo lake pigment |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63225667A true JPS63225667A (en) | 1988-09-20 |
| JPH083052B2 JPH083052B2 (en) | 1996-01-17 |
Family
ID=13096747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62058869A Expired - Fee Related JPH083052B2 (en) | 1987-03-16 | 1987-03-16 | New monoazo lake pigment |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH083052B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5055564A (en) * | 1988-09-15 | 1991-10-08 | Dainippon Ink And Chemicals, Inc. | Modified crystalline monoazo lake pigment |
-
1987
- 1987-03-16 JP JP62058869A patent/JPH083052B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5055564A (en) * | 1988-09-15 | 1991-10-08 | Dainippon Ink And Chemicals, Inc. | Modified crystalline monoazo lake pigment |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH083052B2 (en) | 1996-01-17 |
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| LAPS | Cancellation because of no payment of annual fees |