JPH05295287A - Monoazo lake pigment, its production and pigment dispersion - Google Patents
Monoazo lake pigment, its production and pigment dispersionInfo
- Publication number
- JPH05295287A JPH05295287A JP4122590A JP12259092A JPH05295287A JP H05295287 A JPH05295287 A JP H05295287A JP 4122590 A JP4122590 A JP 4122590A JP 12259092 A JP12259092 A JP 12259092A JP H05295287 A JPH05295287 A JP H05295287A
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- parts
- rosin
- lake
- monoazo lake
- 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
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
- C09B63/00—Lakes
- C09B63/005—Metal lakes of dyes
-
- 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
- C09B67/0004—Coated particulate pigments or dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Paints Or Removers (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、各種の用途、特に印刷
インキ用、塗料用顔料として有用なモノアゾレーキ顔
料、その製造方法および該顔料を用いた顔料分散体に関
する。さらに詳しくは、機械的分散性、ぬれ等の分散性
を向上せしめたモノアゾレーキ顔料、その製造方法およ
び該顔料を用いた顔料分散体に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a monoazo lake pigment which is useful as a pigment for various applications, especially for printing inks and paints, a method for producing the same, and a pigment dispersion using the pigment. More specifically, the present invention relates to a monoazo lake pigment having improved mechanical dispersibility, dispersibility such as wetting, a method for producing the same, and a pigment dispersion using the pigment.
【０００２】[0002]
【従来の技術】可溶性基を有する芳香族アミンをジアゾ
成分とし、β−オキシナフトエ酸、β−ナフトール等を
カップラー成分としてカップリングして得られたモノア
ゾレーキ顔料は、印刷インキ、塗料、プラスチックスの
着色等の各種用途に広く使用されている。これらのモノ
アゾレーキ顔料は、その色調を透明、鮮明にするため、
また分散性を向上するためロジン処理がなされてきた。
このロジン処理は、通常カップラー成分中または染料中
にロジンのアルカリ塩溶液（いわゆるロジンソープ）を
添加し、ついで塩化カルシウム等のレーキ用金属塩を添
加してロジンソープを不溶性のロジンレーキ金属塩とし
て顔料の表面上に析出させる方法である。2. Description of the Related Art Monoazo lake pigments obtained by coupling an aromatic amine having a soluble group as a diazo component and β-oxynaphthoic acid, β-naphthol, etc. as a coupler component are used in printing inks, paints and plastics. Widely used for various purposes such as coloring. These monoazo lake pigments make the color tone transparent and clear.
Also, rosin treatment has been performed to improve dispersibility.
This rosin treatment is usually carried out by adding an alkali salt solution of rosin (so-called rosin soap) to a coupler component or a dye, and then adding a metal salt for lakes such as calcium chloride to the rosin soap as an insoluble rosin lake metal salt on the surface of the pigment. It is a method of depositing on top.
【０００３】上記のロジン処理は、顔料の粒子形状を微
細に制御し、かつ顔料の被覆物質として凝集を抑え、分
散性を向上させ、その結果顔料の透明性、鮮明性を向上
させるという優れた効果を有し、処理量が多い程その効
果は大きい。しかしその反面、ロジン処理には幾つかの
弊害が伴う。例えば、オフセットインキにおける流動性
の低下、耐水性不良に起因する印刷適性の低下、グラビ
アインキにおける高粘度化、塗料における耐衝撃性の低
下等である。The above rosin treatment is excellent in that the particle shape of the pigment is finely controlled, aggregation of the pigment coating material is suppressed, the dispersibility is improved, and the transparency and sharpness of the pigment are improved. It has an effect, and the larger the throughput, the greater the effect. However, on the other hand, the rosin treatment has some adverse effects. For example, the fluidity of the offset ink is reduced, the printability is reduced due to poor water resistance, the viscosity of the gravure ink is increased, and the impact resistance of the paint is reduced.
【０００４】[0004]
【発明が解決しようとする課題】本発明は、ロジンの使
用量を最小限に抑え、新しい表面処理技術により、ロジ
ン処理による上記各種の利点を損なうことなく分散性を
向上したモノアゾレーキ顔料、その製造方法および顔料
分散体の提供を目的とする。DISCLOSURE OF THE INVENTION The present invention is directed to a monoazo lake pigment which has a minimal amount of rosin and has improved dispersibility by a new surface treatment technology without impairing the above-mentioned various advantages of rosin treatment. It is intended to provide a method and a pigment dispersion.
【０００５】[0005]
【課題を解決するための手段】本発明は、可溶性基を有
する芳香族アミンのジアゾニウム塩とカップラー成分と
をカップリングさせたアゾ染料をレーキ化してなるモノ
アゾレーキ顔料、該モノアゾレーキ顔料を被覆するロジ
ン、およびアルキド樹脂からなる被覆処理されたモノア
ゾレーキ顔料を提供する。さらに本発明は、可溶性基を
有する芳香族アミンのジアゾニウム塩とカップラー成分
とをカップリングさせたアゾ染料の溶液中に、ロジンの
水可溶性塩およびアルキド樹脂の水分散体または水溶液
を添加し、ついでレーキ化することからなる被覆処理さ
れたモノアゾレーキ顔料の製造方法、あるいは、可溶性
基を有する芳香族アミンのジアゾニウム塩とカップラー
成分とを、ロジンの水可溶性塩およびアルキド樹脂の水
分散体または水溶液の存在下に、カップリングし、レー
キ化することからなる被覆処理されたモノアゾレーキ顔
料の製造方法を提供する。本発明はさらに、上記被覆処
理モノアゾレーキ顔料とビヒクルとからなる顔料分散体
を提供する。The present invention is directed to a monoazo lake pigment obtained by lakeizing an azo dye obtained by coupling a diazonium salt of an aromatic amine having a soluble group and a coupler component, and a rosin coating the monoazo lake pigment. And a coated monoazo lake pigment comprising an alkyd resin. Furthermore, the present invention is to add a water-soluble salt of rosin and an aqueous dispersion or aqueous solution of an alkyd resin to a solution of an azo dye in which a diazonium salt of an aromatic amine having a soluble group and a coupler component are coupled, and then add A method for producing a coated monoazo lake pigment comprising laking, or a diazonium salt of an aromatic amine having a soluble group and a coupler component, a water-soluble salt of rosin and the presence of an aqueous dispersion or aqueous solution of an alkyd resin. Provided below is a method of making a coated monoazo lake pigment comprising coupling and laking. The present invention further provides a pigment dispersion comprising the above coated monoazo lake pigment and a vehicle.
【０００６】本発明のモノアゾレーキ顔料とは、芳香族
アミンをジアゾ化したジアゾ成分とカップラー成分とを
カップリングした染料をレーキ化したものである。本発
明において、可溶性基を有する芳香族アミンとしては、
例えば１−アミノ−４−メチルベンゼン−２−スルホン
酸（ｐ−トルイジン−ｍ−スルホン酸）、１−アミノ−
４−メチル−５−クロロベンゼン−２−スルホン酸、１
−アミノ−４−クロロ−５−メチルベンゼン−２−スル
ホン酸、１−アミノ−４−メチルベンゼン−３−スルホ
ン酸、１−アミノ−３−メチルベンゼン−４−スルホン
酸等が例示される。The monoazo lake pigment of the present invention is obtained by lakeizing a dye obtained by coupling a diazo component obtained by diazotizing an aromatic amine and a coupler component. In the present invention, as the aromatic amine having a soluble group,
For example, 1-amino-4-methylbenzene-2-sulfonic acid (p-toluidine-m-sulfonic acid), 1-amino-
4-methyl-5-chlorobenzene-2-sulfonic acid, 1
-Amino-4-chloro-5-methylbenzene-2-sulfonic acid, 1-amino-4-methylbenzene-3-sulfonic acid, 1-amino-3-methylbenzene-4-sulfonic acid and the like are exemplified.
【０００７】カップラー成分は、β−オキシナフトエ酸
が代表的であるが、β−ナフトール、アセトアセトアニ
ライドであってもよい。また上記カップラー成分の誘導
体、例えば、低級アルキル基、アルコキシ基またはハロ
ゲン原子で置換された化合物であってもよい。[0007] The coupler component is typically β-oxynaphthoic acid, but may be β-naphthol or acetoacetanilide. Further, it may be a derivative of the above coupler component, for example, a compound substituted with a lower alkyl group, an alkoxy group or a halogen atom.
【０００８】本発明のモノアゾレーキ顔料は、従来公知
のモノアゾレーキ顔料の製造方法に準じて製造される。
すなわち、可溶性基を有する芳香族アミンを常法に従っ
てジアゾ化し、一方上述のカップラー成分を常法に従っ
て調製し、両者を常法に従ってカップリングし、得られ
た染料を顔料レーキ化用金属によりレーキ化する。ま
た、ジアゾ成分および／またはカップラー成分に予め顔
料レーキ化用金属を加えておきカップリングさせてもよ
い。顔料レーキ化用金属としては、カルシウム、バリウ
ム、ストロンチウム、マンガン等が例示される。The monoazo lake pigment of the present invention is produced according to a conventionally known method for producing a monoazo lake pigment.
That is, an aromatic amine having a soluble group is diazotized according to a conventional method, while the above-mentioned coupler component is prepared according to a conventional method, both are coupled according to a conventional method, and the obtained dye is laked with a pigment lake metal. To do. Further, a pigment lake forming metal may be added in advance to the diazo component and / or the coupler component for coupling. Examples of the pigment lake metal include calcium, barium, strontium, manganese and the like.
【０００９】本発明は、アルキド樹脂の水分散体あるい
は水溶液をロジンの水可溶塩と共に顔料に添加して顔料
表面を被覆処理させることに特徴を有する。アルキド樹
脂は、ロジンの水可溶塩例えばナトリウム塩、アンモニ
ウム塩に予め分散あるいは溶解させておき、カップラー
成分中、染料中あるいは顔料中に添加してもよい。アル
キド樹脂の原料としては、アマニ油、ヒマシ油、サフラ
ワー油、大豆油、キリ油、ヤシ油等の油脂またはこれら
の脂肪酸、エチレングリコール、ネオペンチルグリコー
ル、グリセリン、トリメチロールプロパン、ペンタエリ
スリトール等の多価アルコール、無水フタル酸、イソフ
タル酸、テレフタル酸、パラターシャリー安息香酸、ア
ジピン酸、セバチン酸等の多塩基酸が例示される。アル
キド樹脂としては、油脂または油脂脂肪酸４０〜８５重
量部、多価アルコール５〜３０重量部および多塩基酸５
〜３０重量部を、触媒の存在下加熱縮合して得られた油
長４０〜８５％、好ましくは５５〜８５％のアルキド樹
脂が好ましく用いられる。The present invention is characterized in that an aqueous dispersion or aqueous solution of an alkyd resin is added to a pigment together with a water-soluble salt of rosin to coat the surface of the pigment. The alkyd resin may be previously dispersed or dissolved in a water-soluble salt of rosin, such as sodium salt or ammonium salt, and added to the coupler component, the dye or the pigment. As the raw material of the alkyd resin, linseed oil, castor oil, safflower oil, soybean oil, millet oil, fats and oils such as coconut oil or these fatty acids, ethylene glycol, neopentyl glycol, glycerin, trimethylolpropane, pentaerythritol, etc. Examples are polybasic acids such as polyhydric alcohols, phthalic anhydride, isophthalic acid, terephthalic acid, paratertiary benzoic acid, adipic acid and sebacic acid. As the alkyd resin, 40 to 85 parts by weight of oil or fat or oil and fatty acid, 5 to 30 parts by weight of polyhydric alcohol and 5 of polybasic acid.
An alkyd resin having an oil length of 40 to 85%, preferably 55 to 85%, obtained by heating and condensing 30 to 30 parts by weight in the presence of a catalyst is preferably used.
【００１０】本発明の被覆処理されたモノアゾレーキ顔
料は、例えば、アルキド樹脂をロジンの水可溶塩に添加
し、２０〜８０℃で撹拌して分散または溶解させ、この
分散液または溶解液をモノアゾレーキ染料中へ加え、つ
いで１０〜９０℃の温度範囲でレーキ用金属を加えレー
キ化して製造される。ロジンの使用量は、染料に対し３
〜２０重量％、好ましくは５〜１５重量％である。ロジ
ンの使用量が上記範囲の下限よりも少ないと透明性と鮮
明性が低下し、上記範囲の上限よりも多いと着色力が低
下する。アルキド樹脂の使用量は、染料に対し３〜２０
重量％、好ましくは５〜１５重量％である。アルキド樹
脂の使用量が上記範囲の下限よりも少ないと分散性が低
下し、上記範囲の上限よりも多いと着色力が低下する。
アルキド樹脂は、ロジンに対し１０〜１００重量％、好
ましくは５０〜１００重量％の範囲で添加される。In the coated monoazo lake pigment of the present invention, for example, an alkyd resin is added to a water-soluble salt of rosin, and the mixture is dispersed or dissolved by stirring at 20 to 80 ° C., and the dispersion or solution is mixed with the monoazo lake. It is manufactured by adding it to the dye and then adding a metal for lake in the temperature range of 10 to 90 ° C. to form a lake. The amount of rosin used is 3 for the dye
-20% by weight, preferably 5-15% by weight. When the amount of rosin used is less than the lower limit of the above range, the transparency and clarity are reduced, and when it is more than the upper limit of the above range, the coloring power is reduced. The amount of alkyd resin used is 3 to 20 with respect to the dye.
%, Preferably 5 to 15% by weight. When the amount of the alkyd resin used is less than the lower limit of the above range, the dispersibility decreases, and when it is more than the upper limit of the above range, the coloring power decreases.
The alkyd resin is added in the range of 10 to 100% by weight, preferably 50 to 100% by weight, based on rosin.
【００１１】本発明は、印刷インキ用ビヒクル、塗料用
ビヒクル等にに顔料を分散した顔料分散体を提供する。
印刷インキ用ビヒクルは、例えば、オフセットインキで
はロジン変性フェノール樹脂、石油樹脂、アルキド樹
脂、またはこれらの乾性油変性樹脂等の樹脂２０〜５０
重量部、アマニ油、桐油、大豆油等の植物油０〜３０重
量部、ｎ−パラフィン、イソパラフィン、アロマテッ
ク、ナフテン、α−オレフィン等の溶剤１０〜６０重量
部からなる。このオフセットインキ用ビヒクルに本発明
の被覆処理されたモノアゾレーキ顔料を配合し、その他
のインキ溶剤、ドライヤー、レベリング改良剤、増粘剤
等の公知の添加剤を適宜配合して印刷インキ組成物とさ
れる。The present invention provides a pigment dispersion in which a pigment is dispersed in a vehicle for printing ink, a vehicle for paints and the like.
Vehicles for printing inks include, for example, resins 20 to 50 such as rosin-modified phenolic resin, petroleum resin, alkyd resin, or a drying oil-modified resin for offset ink.
Parts by weight, 0 to 30 parts by weight of vegetable oil such as linseed oil, tung oil and soybean oil, and 10 to 60 parts by weight of solvent such as n-paraffin, isoparaffin, aromatech, naphthene and α-olefin. This offset ink vehicle is blended with the coating-treated monoazo lake pigment of the present invention, and other ink solvents, dryers, leveling improvers, thickeners and other known additives are appropriately blended to obtain a printing ink composition. It
【００１２】グラビアインキ用ビヒクルは、例えば、ガ
ムロジン、ウッドロジン、トール油ロジン、石灰化ロジ
ン、ライムロジン、ロジンエステル、マレイン酸樹脂、
ギルソナイト、ダンマル、セラック、ポリアミド樹脂、
ビニル樹脂、ニトロセルロース、環化ゴム、塩化ゴム、
エチルセルロース、酢酸セルロース、エチレン−酢酸ビ
ニル共重合体樹脂、ウレタン樹脂、ポリエステル樹脂、
アルキド樹脂等の樹脂またはこれらの混合物１０〜５０
重量部、ｎ−ヘキサン、トルエン、エタノール、メタノ
ール、アセトン、酢酸エチル、乳酸エチル、セロソル
ブ、ジアセトンアルコール、クロルベンゼン、エチルエ
ーテル、アセタールエチルエーテル、アセト酢酸エチ
ル、酢酸ブチルセロソルブ等の溶剤３０〜８０重量部か
らなる。上記重量部のビヒクルに本発明のモノアゾレー
キ顔料３〜３５重量部、硫酸バリウム、炭酸バリウム、
炭酸カルシウム、石膏、アルミナ白、クレー、シリカ、
シリカ白、タルク、ケイ酸カルシウム、沈降性炭酸マグ
ネシウム等の体質顔料０〜２０重量部を加え、その他補
助剤として、可塑剤、紫外線防止剤、酸化防止剤、帯電
防止剤等を適宜添加してグラビアインキ組成物とされ
る。Vehicles for gravure ink include, for example, gum rosin, wood rosin, tall oil rosin, calcified rosin, lime rosin, rosin ester, maleic acid resin,
Gilsonite, dammar, shellac, polyamide resin,
Vinyl resin, nitrocellulose, cyclized rubber, chlorinated rubber,
Ethyl cellulose, cellulose acetate, ethylene-vinyl acetate copolymer resin, urethane resin, polyester resin,
Resins such as alkyd resins or mixtures thereof 10-50
30 to 80 parts by weight of a solvent such as n-hexane, toluene, ethanol, methanol, acetone, ethyl acetate, ethyl lactate, cellosolve, diacetone alcohol, chlorobenzene, ethyl ether, acetal ethyl ether, ethyl acetoacetate, butyl cellosolve acetate. Consists of parts. 3 to 35 parts by weight of the monoazo lake pigment of the present invention, barium sulfate, barium carbonate, and
Calcium carbonate, gypsum, white alumina, clay, silica,
0 to 20 parts by weight of extender pigment such as silica white, talc, calcium silicate, and precipitated magnesium carbonate is added, and other auxiliary agents such as a plasticizer, an anti-UV agent, an antioxidant, and an antistatic agent are appropriately added. A gravure ink composition.
【００１３】塗料用ビヒクルは、例えば、アクリル樹
脂、アルキド樹脂、エポキシ樹脂、塩化ゴム、塩化ビニ
ル、合成樹脂エマルジョン、シリコーン樹脂、水溶性樹
脂、ポリウレタン、ポリエステル、メラミン樹脂、ユリ
ア樹脂またはこれらの混合物８０〜２０重量％と炭化水
素、アルコール、ケトン、エーテルアルコール、エーテ
ル、エステル、水等の溶剤６０〜１０重量％とからな
る。この塗料用ビヒクル９９.９〜５５重量％に本発明
の顔料０.１〜１５重量％、その他の補助剤や体質顔料
０〜３０重量％を加えて塗料とされる。The vehicle for paint is, for example, acrylic resin, alkyd resin, epoxy resin, chlorinated rubber, vinyl chloride, synthetic resin emulsion, silicone resin, water-soluble resin, polyurethane, polyester, melamine resin, urea resin or a mixture thereof 80. .About.20% by weight and 60 to 10% by weight of a solvent such as hydrocarbon, alcohol, ketone, ether alcohol, ether, ester and water. A paint is prepared by adding 0.1 to 15% by weight of the pigment of the present invention and 0 to 30% by weight of other auxiliary agents and extender pigments to 99.9 to 55% by weight of the vehicle for paint.
【００１４】以下実施例に基づき本発明をより詳細に説
明する。例中、特に断りの無い限り部は重量部を、％は
重量％を意味する。 実施例１ １−アミノ−４−メチルベンゼン−２−スルホン酸９
０.６部、１−アミノ−４−メチルベンゼン−３−スル
ホン酸２.９部、２−アミノナフタレン−１−スルホン
酸１.８部を水１５００部と水酸化ナトリウム２０部か
らなる溶液に溶解する。これに３５％塩酸１２４部を加
え酸析後、氷１０００部を加え０℃に冷却する。水１０
０部と亜硫酸ナトリウム３５部からなる溶液を加え、３
℃以下で３０分間撹拌してジアゾ成分を得た。The present invention will be described in more detail based on the following examples. In the examples, "parts" means "parts by weight" and "%" means "% by weight" unless otherwise specified. Example 1 1-Amino-4-methylbenzene-2-sulfonic acid 9
0.6 part, 1-amino-4-methylbenzene-3-sulfonic acid 2.9 parts, 2-aminonaphthalene-1-sulfonic acid 1.8 parts into a solution consisting of 1500 parts water and 20 parts sodium hydroxide. Dissolve. To this, 124 parts of 35% hydrochloric acid is added, and after acid precipitation, 1000 parts of ice is added and cooled to 0 ° C. Water 10
Add a solution consisting of 0 part and 35 parts of sodium sulfite and add 3 parts.
The diazo component was obtained by stirring at 30 ° C. or lower for 30 minutes.
【００１５】β−オキシナフトエ酸９５部を水３０００
部と水酸化ナトリウム５１部とからなる溶液に溶解し、
１５℃に冷却したものをカップラー成分とする。カップ
ラー成分にジアゾ成分を２０分間で滴下し、カップリン
グ反応を進め、３０分間撹拌して染料を得た。次にヒマ
シ油８０部、ペンタエリスリトール６部、テレフタル酸
１４部を触媒存在下に合成したアルキド樹脂２１.２部
（油長８０％、染料に対し１０％）を２５％ロジンソー
プ８４.８部（染料に対し樹脂固形分として１０％）に
加え、４０℃で溶解した。このアルキド−ロジン溶液を
上記染料に加え、１％水酸化ナトリウムでｐＨ１１.５
に調整した。これに３５％塩化カルシウム水溶液を３０
０部加え、３時間撹拌を続けてレーキ化反応を完結し
た。これを８０℃に加熱後、濾過、水洗、乾燥、粉砕し
て２５４部のモノアゾレーキ顔料を得た。95 parts of β-oxynaphthoic acid was added to 3000 parts of water.
And a solution of 51 parts of sodium hydroxide,
What was cooled to 15 ° C was used as the coupler component. The diazo component was added dropwise to the coupler component over 20 minutes to advance the coupling reaction and stirred for 30 minutes to obtain a dye. Next, 21.2 parts of alkyd resin (80% oil length, 10% based on the dye) prepared by synthesizing 80 parts of castor oil, 6 parts of pentaerythritol, and 14 parts of terephthalic acid in the presence of a catalyst, 84.8 parts of rosin soap ( It was added to the dye as a resin solid content of 10%) and dissolved at 40 ° C. Add this alkyd-rosin solution to the above dye and add 1% sodium hydroxide to pH 11.5.
Adjusted to. Add 30% of 35% calcium chloride solution to this.
0 part was added and stirring was continued for 3 hours to complete the lake reaction. This was heated to 80 ° C., filtered, washed with water, dried and pulverized to obtain 254 parts of a monoazo lake pigment.
【００１６】比較例１ アルキド−ロジン溶液の代わりに２５％ロジンソープ８
４.８部（染料に対し樹脂固形分として１０％）を使用
した他は実施例１と同様に操作してモノアゾレーキ顔料
を得た。Comparative Example 1 25% rosin soap 8 instead of the alkyd-rosin solution
A monoazo lake pigment was obtained in the same manner as in Example 1 except that 4.8 parts (10% of resin solid content based on the dye) was used.
【００１７】比較例２ アルキド−ロジン溶液の代わりに２５％ロジンソープ１
６９.６部（染料に対し樹脂固形分として２０％）を使
用した他は実施例１と同様に操作してモノアゾレーキ顔
料を得た。Comparative Example 2 25% rosin soap 1 instead of the alkyd-rosin solution
A monoazo lake pigment was obtained in the same manner as in Example 1 except that 69.6 parts (20% as resin solid content based on the dye) was used.
【００１８】参考例 実施例１、比較例１および比較例２で得られた顔料のオ
フセットインキ用としての試験を実施した。使用ビヒク
ルはタマノール３６１（荒川化学(株)製、ロジン変性フ
ェノール樹脂）５０部に対し、アマニ油２０部、５号ソ
ルベント（日本石油(株)製、インキ溶剤）３０部を加
え、２００℃に加熱して溶解した。このビヒクル９８部
にオクチル酸アルミニウム２部を加えオフセットインキ
用ビヒクルとした。以下次の試験を実施した。Reference Example The pigments obtained in Example 1, Comparative Example 1 and Comparative Example 2 were tested for offset ink. The vehicle used was Tamanol 361 (Arakawa Chemical Co., Ltd., rosin-modified phenolic resin) 50 parts, linseed oil 20 parts, No. 5 solvent (Nippon Oil Co., Ltd., ink solvent) 30 parts, and the temperature was increased to 200 ° C. It was heated to dissolve. 2 parts of aluminum octylate were added to 98 parts of this vehicle to prepare a vehicle for offset ink. The following tests were conducted below.
【００１９】インキビヒクルへの濡れ試験：得られたオ
フセットインキ用ビヒクル７０部を紙コップに入れ、こ
れに各顔料２０部を加え、均一となるように混合撹拌し
てプレミックスインキを作成した。比較例１の顔料では
８分、比較例２の顔料では６分をそれぞれ均一となるま
でに要したが、実施例１の顔料では３分で均一となっ
た。このことはアルキド処理によりビヒクルへの濡れが
向上したことを意味する。Wetting test to ink vehicle: 70 parts of the obtained vehicle for offset ink was put into a paper cup, 20 parts of each pigment was added thereto, and mixed and stirred to be uniform to prepare a premix ink. It took 8 minutes for the pigment of Comparative Example 1 and 6 minutes for the pigment of Comparative Example 2 to be uniform, but the pigment for Example 1 was uniform for 3 minutes. This means that the alkyd treatment improved the wetting of the vehicle.
【００２０】分散性試験：各プレミックスインキを３本
ロールで練肉すると、比較例１の顔料では４パスで、比
較例２の顔料では３パスで粗粒子が消失した。これに対
し実施例１の顔料では２パスで粗粒子が消失した。この
ことはアルキド処理により分散性が向上したことを意味
する。Dispersibility test: When each premix ink was kneaded with three rolls, coarse particles disappeared after 4 passes with the pigment of Comparative Example 1 and after 3 passes with the pigment of Comparative Example 2. On the other hand, with the pigment of Example 1, coarse particles disappeared in 2 passes. This means that the dispersibility was improved by the alkyd treatment.
【００２１】流動性試験：各プレミックスインキを３本
ロールで練肉した各インキの流動性を２５℃で６０秒の
フローをスプレッドメーターで測定した。比較例１の顔
料では１７.２であるに対し、比較例２の顔料では１５.
８と流動性が大きく低下した。実施例１の顔料を使用し
た場合には１７.５であり、流動性の低下は認められな
かった。このことはロジン処理量の増加は流動性を低下
させるが、アルキド処理は流動性を低下させないことを
意味する。Fluidity test: The fluidity of each ink prepared by kneading each premix ink with three rolls was measured at 25 ° C. for 60 seconds with a spread meter. The pigment of Comparative Example 1 was 17.2, whereas the pigment of Comparative Example 2 was 15.2.
The fluidity was significantly reduced to 8. When the pigment of Example 1 was used, it was 17.5, and no decrease in fluidity was observed. This means that increasing the amount of rosin treatment reduces the fluidity, whereas alkyd treatment does not reduce the fluidity.
【００２２】光沢度試験：各プレミックスインキを３本
ロールで練肉した後、タック９.０〜９.５に調整したイ
ンキをアート紙へ展色刷りしたときの光沢は、比較例１
の顔料に比べ比較例２の顔料では−７％と低下した。こ
れに対し実施例１の顔料では比較例１の顔料よりも５％
高かった。Gloss test: Each premix ink was kneaded with three rolls, and the gloss of the ink adjusted to a tack of 9.0 to 9.5 was printed on art paper in a comparative example 1
The pigment of Comparative Example 2 had a decrease of -7% as compared with the pigment of Example 1. On the other hand, the pigment of Example 1 is 5% more than the pigment of Comparative Example 1.
it was high.
【００２３】オフセット印刷適性試験：各プレミックス
インキを３本ロールで練肉して得られたインキを水に乳
化して得られた水可溶分を含むインキ抽出水を作成し、
表面張力を測定した。比較例１の顔料では６４.３dyne/
cmであった。比較例２の顔料では５０.６dyne/cmであっ
た。これに対し、実施例１の顔料では６４.１dyne/cmで
あり、比較例１と相違がなかった。このことはロジン処
理量の増加はオフセット印刷適性に悪影響を与えると推
定されるが、アルキド処理はオフセット印刷適性に悪影
響を与えないものと推定される。Offset printability test: Each premix ink was kneaded with three rolls to emulsify the ink obtained in water to prepare an ink extraction water containing water-soluble components,
The surface tension was measured. In the pigment of Comparative Example 1, 64.3 dyne /
It was cm. The pigment of Comparative Example 2 had a density of 50.6 dyne / cm. In contrast, the pigment of Example 1 had 64.1 dyne / cm, which was not different from Comparative Example 1. It is estimated that the increase in the amount of rosin treatment adversely affects the offset printability, but the alkyd treatment does not affect the offset printability.
【００２４】実施例２ １−アミノ−４−メチルベンゼン−２−スルホン酸９２
部、１−アミノ−４−メチルベンゼン−３−スルホン酸
９.２部を水１５００部と水酸化ナトリウム２０部から
なる溶液に溶解した。これに３５％塩酸１２４部を加え
酸析後、氷１０００部を加え０℃に冷却した。この冷却
液に水１００部に亜硫酸ナトリウム３５部を溶解した溶
液を加え、３℃以下で３０分間撹拌してジアゾ成分を得
た。Example 2 1-Amino-4-methylbenzene-2-sulfonic acid 92
And 9.2 parts of 1-amino-4-methylbenzene-3-sulfonic acid were dissolved in a solution of 1500 parts of water and 20 parts of sodium hydroxide. To this, 124 parts of 35% hydrochloric acid was added, and after acid precipitation, 1000 parts of ice was added and cooled to 0 ° C. A solution prepared by dissolving 35 parts of sodium sulfite in 100 parts of water was added to this cooling liquid, and the mixture was stirred at 3 ° C. or lower for 30 minutes to obtain a diazo component.
【００２５】ヤシ油８２部、ペンタエリスリトール６
部、テレフタール酸１４部から触媒存在下に合成したア
ルキド樹脂１０.６部（油長８２％、染料に対し５％）
を、２５％ロジンソープ８４.８部（染料に対し樹脂固
形分として１０％）に６０℃で分散した。この水性分散
液を、β−オキシナフトエ酸９５部を水３０００部と水
酸化ナトリウム５１部からなる溶液に溶解した水溶液中
に加え、１５℃に調整し、カップラー成分を得た。カッ
プラー成分にジアゾ成分を２０分間かけて滴下し、カッ
プリング反応を進めた。これに３５％塩化カルシウム水
溶液３００部を加え、３時間撹拌してレーキ化反応を完
結させた。ついで８０℃に加熱した後、濾過、水洗、乾
燥、粉砕して２３３部のモノアゾレーキ顔料を得た。82 parts of coconut oil, pentaerythritol 6
Parts, 10.6 parts of alkyd resin synthesized from 14 parts of terephthalic acid in the presence of a catalyst (oil length 82%, dye 5%)
Was dispersed in 84.8 parts of 25% rosin soap (10% as resin solid content based on the dye) at 60 ° C. This aqueous dispersion was added to an aqueous solution prepared by dissolving 95 parts of β-oxynaphthoic acid in a solution consisting of 3000 parts of water and 51 parts of sodium hydroxide, and adjusted to 15 ° C. to obtain a coupler component. The diazo component was added dropwise to the coupler component over 20 minutes to advance the coupling reaction. To this, 300 parts of 35% calcium chloride aqueous solution was added and stirred for 3 hours to complete the lake reaction. Then, the mixture was heated to 80 ° C., filtered, washed with water, dried and pulverized to obtain 233 parts of a monoazo lake pigment.
【００２６】比較例３ アルキド−ロジン分散液の代わりに２５％ロジンソープ
８４.８部（染料に対し樹脂固形分として１０％）を使
用した他は実施例２と同様に操作してモノアゾレーキ顔
料を得た。Comparative Example 3 A monoazo lake pigment was obtained in the same manner as in Example 2 except that 84.8 parts of 25% rosin soap (10% as resin solid content based on the dye) was used in place of the alkyd-rosin dispersion. It was
【００２７】比較例４ アルキド−ロジン分散液の代わりに２５％ロジンソープ
１２７.２部（染料に対し樹脂固形分として１５％）を
使用した他は実施例２と同様に操作してモノアゾレーキ
顔料を得た。Comparative Example 4 A monoazo lake pigment was obtained in the same manner as in Example 2 except that 127.2 parts of 25% rosin soap (15% as resin solid content based on the dye) was used in place of the alkyd-rosin dispersion. It was
【００２８】参考例２ 実施例２、比較例３および比較例４で得られた顔料につ
いて、グラビアインキ試験および油性塗料試験を実施し
た。 濃色インキの調製：顔料１０部、ライムロジン系ワニス
（固形分２０％、トルエン７５％、可塑剤５％）９０部
および直径３ｍｍのガラスビーズを２２０ｃｃのマヨネ
ースビンに入れ、ペイントコンディショナーで２時間振
盪して、濃色インキを調製した。Reference Example 2 The pigments obtained in Example 2, Comparative Example 3 and Comparative Example 4 were subjected to a gravure ink test and an oil paint test. Preparation of dark ink: 10 parts of pigment, 90 parts of lime rosin varnish (solid content 20%, toluene 75%, plasticizer 5%) and glass beads having a diameter of 3 mm were put in a 220 cc mayonnaise bottle, and shaken for 2 hours in a paint conditioner. Then, a dark ink was prepared.
【００２９】粘度試験：濃色インキの粘度をＮｏ．３ザ
ーンカップで測定した。比較例３の顔料では３１秒であ
った。比較例４の顔料では４８秒と粘度が高かったのに
対し、実施例２の顔料では３１秒と粘度の上昇は見られ
なかった。このことは、ロジン処理量の増加は粘度を上
昇させるのに対し、アルキド処理は上昇させないことを
意味する。Viscosity test: The viscosity of the dark color ink 3 Measured with Zahn cup. It was 31 seconds for the pigment of Comparative Example 3. The pigment of Comparative Example 4 had a high viscosity of 48 seconds, whereas the pigment of Example 2 did not show an increase of viscosity of 31 seconds. This means that increasing rosin treatment increases viscosity while alkyd treatment does not.
【００３０】着色力の判定：濃色インキ１部に白インキ
１０部を混練した淡色インキを調整してコート紙に展色
したときの着色力を目視で判定した。比較例３の顔料に
比べ比較例４の顔料では約−３％、実施例２の顔料では
約＋３％と高着色力であった。このことは、アルキド処
理により分散性が向上し、高着色力になったことを意味
する。Judgment of tinting strength: A tinting strength when a light color ink prepared by kneading 1 part of dark ink with 10 parts of white ink was spread and coated on coated paper was visually judged. Compared with the pigment of Comparative Example 3, the pigment of Comparative Example 4 had a high tinting strength of about -3%, and the pigment of Example 2 had about + 3%. This means that the dispersibility was improved by the alkyd treatment and the coloring power was increased.
【００３１】光沢度試験：各濃色インキにトルエンを加
え、Ｎｏ．３ザーンカップで１５秒となる様に調整後、
コート紙に展色したときの光沢は、比較例３の顔料に比
べ比較例４の顔料では−５％と低下したのに対し、実施
例２の顔料では＋４％と高光沢であった。このことは、
アルキド処理により分散性が向上し、高光沢になったこ
とを意味する。Glossiness test: Toluene was added to each dark color ink, and No. After adjusting to 3 seconds for 15 seconds,
The gloss of the pigment spread on the coated paper was -5%, which was lower than that of the pigment of Comparative Example 3 by 5%, whereas the pigment of Example 2 was + 4%, which was high gloss. This is
It means that dispersibility was improved and high gloss was obtained by the alkyd treatment.
【００３２】油性塗料の調製：顔料８部、アルキド樹脂
ワニス５０部、メラミン樹脂ワニス３０部およびシンナ
ー１２部を直径２ｍｍのスチールビーズと共に２２０ｃ
ｃのマヨネーズビンに入れ、ペイントコンディショナー
で９０分振盪して油性塗料を調製した。この油性塗料の
着色力、光沢、耐衝撃性共に実施例２の顔料では比較例
３および比較例４の顔料よりも優れていた。Preparation of oil paint: 8 parts of pigment, 50 parts of alkyd resin varnish, 30 parts of melamine resin varnish and 12 parts of thinner together with steel beads having a diameter of 2 mm, 220c.
It was put in the mayonnaise bottle of c and shaken for 90 minutes with a paint conditioner to prepare an oil-based paint. The pigment of Example 2 was superior to the pigments of Comparative Examples 3 and 4 in terms of tinting strength, gloss and impact resistance of this oil-based paint.
【００３３】[0033]
【発明の効果】本発明によれば、ロジン使用量を最小限
にした新規表面処理により、印刷適性を低下させること
なく、機械的分散性、濡れなどの分散性を向上せしめた
モノアゾレーキ顔料、該顔料の製造方法および該顔料の
分散体が提供される。INDUSTRIAL APPLICABILITY According to the present invention, a monoazo lake pigment improved in mechanical dispersibility and dispersibility such as wetting without deteriorating printability by a novel surface treatment in which the amount of rosin used is minimized, Methods of making pigments and dispersions of the pigments are provided.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 水野 昇 東京都中央区京橋２丁目３番13号 東洋イ ンキ製造株式会社内 (72)発明者 梶原 盛久 東京都中央区京橋２丁目３番13号 東洋イ ンキ製造株式会社内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Noboru Mizuno 2-33-1 Kyobashi, Chuo-ku, Tokyo Toyo Inki Manufacturing Co., Ltd. Toyo Inki Manufacturing Co., Ltd.
Claims (4)
ニウム塩とカップラー成分とをカップリングさせたアゾ
染料をレーキ化してなるモノアゾレーキ顔料、該モノア
ゾレーキ顔料を被覆するロジン、およびアルキド樹脂か
らなる被覆処理されたモノアゾレーキ顔料。1. A monoazo lake pigment obtained by lake-forming an azo dye obtained by coupling a diazonium salt of an aromatic amine having a soluble group and a coupler component, a rosin coating the monoazo lake pigment, and a coating treatment comprising an alkyd resin. Monoazo lake pigment.
ニウム塩とカップラー成分とをカップリングさせたアゾ
染料の溶液中に、ロジンの水可溶性塩およびアルキド樹
脂の水分散体または水溶液を添加し、ついでレーキ化す
ることからなる被覆処理されたモノアゾレーキ顔料の製
造方法。2. A water-soluble salt of rosin and an aqueous dispersion or aqueous solution of an alkyd resin are added to a solution of an azo dye in which a diazonium salt of an aromatic amine having a soluble group and a coupler component are coupled, and then added. A process for producing a monoazo lake pigment having a coating treatment, which comprises forming a lake.
ニウム塩とカップラー成分とを、ロジンの水可溶性塩お
よびアルキド樹脂の水分散体または水溶液の存在下に、
カップリングし、レーキ化することからなる被覆処理さ
れたモノアゾレーキ顔料の製造方法。3. A diazonium salt of an aromatic amine having a soluble group and a coupler component are present in the presence of a water-soluble salt of rosin and an aqueous dispersion or aqueous solution of an alkyd resin,
A method for producing a coated monoazo lake pigment, which comprises coupling and lake formation.
顔料とビヒクルとからなる顔料分散体。4. A pigment dispersion comprising the coated monoazo lake pigment according to claim 1 and a vehicle.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12259092A JP3216225B2 (en) | 1992-04-16 | 1992-04-16 | Monoazo lake pigment, production method thereof and pigment dispersion |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12259092A JP3216225B2 (en) | 1992-04-16 | 1992-04-16 | Monoazo lake pigment, production method thereof and pigment dispersion |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05295287A true JPH05295287A (en) | 1993-11-09 |
| JP3216225B2 JP3216225B2 (en) | 2001-10-09 |
Family
ID=14839694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12259092A Expired - Fee Related JP3216225B2 (en) | 1992-04-16 | 1992-04-16 | Monoazo lake pigment, production method thereof and pigment dispersion |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3216225B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07188575A (en) * | 1993-12-28 | 1995-07-25 | Toyo Ink Mfg Co Ltd | Pigment water paste for offset ink, its production and use thereof |
| WO1997001607A1 (en) * | 1993-12-28 | 1997-01-16 | Toyo Ink Manufacturing Co., Ltd. | Aqueous pigment paste for offset ink, process for producing the paste, and use thereof |
-
1992
- 1992-04-16 JP JP12259092A patent/JP3216225B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07188575A (en) * | 1993-12-28 | 1995-07-25 | Toyo Ink Mfg Co Ltd | Pigment water paste for offset ink, its production and use thereof |
| WO1997001607A1 (en) * | 1993-12-28 | 1997-01-16 | Toyo Ink Manufacturing Co., Ltd. | Aqueous pigment paste for offset ink, process for producing the paste, and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3216225B2 (en) | 2001-10-09 |
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