JPH0977994A - Pigment dispersant for nonaqueous system, pigment composition containing the same, and nonaqueous pigment dispersion - Google Patents
Pigment dispersant for nonaqueous system, pigment composition containing the same, and nonaqueous pigment dispersionInfo
- Publication number
- JPH0977994A JPH0977994A JP7238165A JP23816595A JPH0977994A JP H0977994 A JPH0977994 A JP H0977994A JP 7238165 A JP7238165 A JP 7238165A JP 23816595 A JP23816595 A JP 23816595A JP H0977994 A JPH0977994 A JP H0977994A
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- parts
- dispersant
- dispersion
- aqueous
- 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.)
- Pending
Links
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、顔料粒子の分散剤
に関するものであり、更に詳しくは、印刷インキや塗料
の使用適性の向上を図る非水系用顔料分散剤、およびそ
れを含有する顔料組成物、ならびに非水系顔料分散体に
関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a dispersant for pigment particles, and more specifically, a non-aqueous pigment dispersant for improving suitability for use in printing inks and paints, and a pigment composition containing the same. And a non-aqueous pigment dispersion.
【０００２】[0002]
【従来の技術】一般に各種コーティングまたはインキ組
成物中において、鮮明な色調と高い着色力を発揮する実
用上有用な顔料は微細な粒子からなっている。しかしな
がら顔料の微細な粒子は、オフセットインキ、グラビア
インキおよび塗料のような非水性ビヒクルに分散する場
合、安定な分散体を得るのは難しく、製造作業上および
得られる製品の価値に重大な影響を及ぼす種々の問題を
引き起こすことが知られている。例えば、微細な粒子か
らなる顔料を含む分散体は往々にして高粘度を示し、分
散機から分散体をの取り出し、輸送したりする際に困難
を生じる。また、分散体が貯蔵中にゲル化を起こし使用
できなくなる場合もある。あるいは、異種の顔料を混合
して使用する場合、顔料の凝集による色分かれや沈降な
どの現象により、展色物において、色むらや著しい着色
力の低下を引き起こすことがある。さらに、このような
不安定な分散体の場合、展色物の塗膜表面状態が損なわ
れやすく、例えば光沢の低下、レベリング不良等が発生
することがある。2. Description of the Related Art Generally, in various coatings or ink compositions, practically useful pigments exhibiting a clear color tone and high tinting strength are composed of fine particles. However, when the fine particles of the pigment are dispersed in non-aqueous vehicles such as offset inks, gravure inks and paints, it is difficult to obtain a stable dispersion, which has a significant effect on the manufacturing operation and the value of the resulting product. It is known to cause various problems. For example, dispersions containing pigments consisting of fine particles often exhibit high viscosities, which makes it difficult to remove and transport the dispersion from the disperser. In some cases, the dispersion may gel during storage and become unusable. Alternatively, when different kinds of pigments are mixed and used, a phenomenon such as color separation or sedimentation due to aggregation of the pigments may cause color unevenness or a marked decrease in coloring power in a color-developed product. Furthermore, in the case of such an unstable dispersion, the surface state of the coating film of the color-developed product is likely to be impaired, and, for example, lowering of gloss and poor leveling may occur.
【０００３】また、一部の有機顔料では顔料の結晶状態
が変化することがある。すなわち、オフセットインキ、
グラビアインキおよび塗料等の非水性ビヒクル中でエネ
ルギー的に不安定な顔料の結晶粒子が大きさ、形態を変
化させて安定状態に移行するために展色物において著し
い色相の変化、着色力の現象、粗粒子の発生等により商
品価値を損なうことがある。In some organic pigments, the crystalline state of the pigment may change. That is, offset ink,
In the non-aqueous vehicle such as gravure ink and paint, the crystal particles of the energy-unstable pigment change in size and morphology and shift to a stable state, resulting in a marked change in hue and the phenomenon of coloring power in the developed product. , The product value may be impaired due to the generation of coarse particles.
【０００４】以上のような種々の問題点を解決するため
に、これまでも数多くの提案がされている。その内容を
技術的手法から分類すると大きく次のような３つに分け
られる。 １．USP3370971号およびUSP2965511号に見られるよう
に、酸化ケイ素、酸化アルミニウムおよび第３級ブチル
安息香酸などの無色の化合物で顔料粒子を被覆するもの
である。 ２．特公昭41-2466 号公報およびUSP2855403号に代表さ
れるように、有機顔料を母体骨格とし、側鎖にスルホン
基、スルホンアミド基、アミノメチル基およびフタルイ
ミドメチル基などの置換基を導入して得られる化合物を
混合する方法である。 ３．特公昭57-25251号公報および特開昭61-285266 号公
報に代表されるようなポリマー分散剤を混合する方法で
ある。In order to solve the above various problems, many proposals have been made so far. The contents can be roughly classified into the following three categories according to the technical method. 1. As is found in USP 3370971 and USP 2965511, pigment particles are coated with a colorless compound such as silicon oxide, aluminum oxide and tertiary butyl benzoic acid. 2. As represented by Japanese Examined Patent Publication No. 41-2466 and USP 2855403, it is obtained by using an organic pigment as a base skeleton and introducing a substituent such as a sulfone group, a sulfonamide group, an aminomethyl group and a phthalimidomethyl group into a side chain. It is a method of mixing the compound. 3. This is a method of mixing a polymer dispersant represented by JP-B-57-25251 and JP-A-61-285266.
【０００５】上記２の場合は、１の場合に比べ、非水性
ビヒクル中での顔料の非集合性、結晶安定性などに関す
る効果が著しく大きく、また比較的簡単な混合方法によ
っても十分な効果が得られる場合が多い。しかし、それ
ぞれの化合物の効果は使用するビヒクルの組成に大きく
影響され、全てのビヒクルに有効な汎用性に富む化合物
は見出されていない。上記３の場合は、比較的ビヒクル
組成の影響が少なく汎用性のある方法であるが、ポリマ
ー分散剤と顔料粒子の相互作用が弱いため、顔料の分散
安定性という点では十分な効果が得られない場合が多
い。In the case of the above 2, compared with the case of 1, the effect on the non-aggregation property of the pigment in the non-aqueous vehicle, the crystal stability, etc. is remarkably large, and a sufficient effect can be obtained even by a relatively simple mixing method. Often obtained. However, the effect of each compound is largely influenced by the composition of the vehicle used, and no compound having a wide range of versatility effective for all vehicles has been found. In the case of 3 above, the method is relatively versatile with little influence of the vehicle composition, but since the interaction between the polymer dispersant and the pigment particles is weak, a sufficient effect can be obtained in terms of pigment dispersion stability. Often not.
【０００６】一方、特開昭63-175080 号公報および特開
平4-139262号公報には、有機色素とポリマーを結合させ
たポリマー分散剤が提示されている。ポリマー分散剤に
含まれる有機色素と顔料粒子の相互作用が強くなるため
ポリマー分散剤の顔料粒子への吸着が促進され分散性が
向上するものと考えられる。しかしながら、該公報記載
のポリマー分散剤は、ポリマー中にランダムに存在する
官能基を用いて、有機色素とポリマーとを結合してい
る。この方法によると、ポリマー中にランダムに有機色
素が導入されるために、ポリマー部分と分散媒との親和
性が弱まり、分散安定化に十分な吸着層を確保しにくく
なったり、また、ポリマー中への有機色素あるいは複素
環の導入量が増加すると分散媒への溶解性が減少するた
め、分散安定化に十分な吸着層を確保できなくなったり
するという問題がある。On the other hand, JP-A-63-175080 and JP-A-4-139262 disclose a polymer dispersant in which an organic dye and a polymer are bonded. It is considered that since the interaction between the organic dye contained in the polymer dispersant and the pigment particles becomes strong, the adsorption of the polymer dispersant to the pigment particles is promoted and the dispersibility is improved. However, the polymer dispersant described in this publication uses a functional group randomly present in the polymer to bond the organic dye and the polymer. According to this method, since the organic dye is randomly introduced into the polymer, the affinity between the polymer portion and the dispersion medium is weakened, and it becomes difficult to secure an adsorption layer sufficient for dispersion stabilization. When the amount of the organic dye or the heterocycle introduced into the polymer increases, the solubility in the dispersion medium decreases, so that there is a problem that it becomes impossible to secure an adsorption layer sufficient for dispersion stabilization.
【０００７】[0007]
【発明が解決しようとする課題】本発明は、前記の種々
の欠点を改良し、良好に顔料を分散することができ、し
かも工業的に有利に製造できる非水系用顔料分散剤、お
よびそれを用いた顔料組成物、ならびに非水系顔料分散
体を提供するものである。DISCLOSURE OF THE INVENTION The present invention improves the above-mentioned various drawbacks, can disperse a pigment satisfactorily, and can be industrially advantageously produced, and a non-aqueous pigment dispersant for the same. The present invention provides a pigment composition used and a non-aqueous pigment dispersion.
【０００８】[0008]
【課題を解決するための手段】すなわち、第１の発明
は、有機色素および／または複素環を有する連鎖移動剤
を用いることにより得られる、アクリル系重合体の末端
にのみ有機色素および／または複素環を有する非水系用
顔料分散剤であり、第２の発明は、顔料および第１の発
明の非水系用顔料分散剤からなる顔料組成物である。さ
らに、第３の発明は、顔料、第１の発明の非水系用顔料
分散剤および非水系樹脂からなる非水系顔料分散体であ
る。[Means for Solving the Problems] That is, the first invention is to obtain an organic dye and / or a heterocycle only at the terminal of an acrylic polymer, which is obtained by using an organic dye and / or a chain transfer agent having a heterocycle. A non-aqueous pigment dispersant having a ring, and a second invention is a pigment composition comprising the pigment and the non-aqueous pigment dispersant of the first invention. Further, a third invention is a non-aqueous pigment dispersion comprising a pigment, the non-aqueous pigment dispersant of the first invention and a non-aqueous resin.
【０００９】[0009]
【発明の実施の形態】本発明の顔料分散剤は、ポリマー
部分の片末端あるいは両末端のみに有機色素および／ま
たは複素環を有する構造であるため、顔料表面に効率よ
く有機色素あるいは複素環を吸着せしめ、ポリマー部分
と分散媒との良好な親和性によって、顔料と有機色素あ
るいは複素環との係る吸着を効率よく安定化せしめるこ
とができるようになったものである。また、合成手法上
もポリマーの末端を用いることによって、ポリマー中に
精度良く、少ない量の有機色素あるいは複素環を導入す
ることができるようになったものである。BEST MODE FOR CARRYING OUT THE INVENTION Since the pigment dispersant of the present invention has a structure having an organic dye and / or a heterocycle only at one end or both ends of the polymer portion, the organic dye or the heterocycle can be efficiently attached to the pigment surface. Adsorption, and the good affinity between the polymer portion and the dispersion medium makes it possible to efficiently stabilize the adsorption between the pigment and the organic dye or the heterocycle. Further, in terms of the synthetic method, by using the end of the polymer, it is possible to accurately introduce a small amount of the organic dye or the heterocycle into the polymer.
【００１０】以下、本発明を詳細に説明する。本発明の
顔料分散剤は、有機色素あるいは複素環を有する連鎖移
動剤を用いてなる水性アクリル系重合体である。係る連
鎖移動剤のうち有機色素を有するものとしては、例えば
フタロシアニン系、不溶性アゾ系、アゾレーキ系、アン
トラキノン系、キナクリドン系、ジオキサジン系、ジケ
トピロロピロール系、アントラピリジン系、アンサンス
ロン系、インダンスロン系、フラバンスロン系、ペリノ
ン系、ペリレン系、チオインジゴ系等がある。また、複
素環を有するものとしては、例えばチオフェン、フラ
ン、キサンテン、ピロール、イミダゾール、イソインド
リン、イソインドリノン、ベンズイミダゾロン、インド
ール、キノリン、カルバゾール、アクリジン、アクリド
ン、アントラキノン等が挙げられる。有機色素および／
または複素環を有する連鎖移動剤は、有機色素と−ＳＨ
有するもの、または複素環と−ＳＨを有するものであ
り、例えばメルカプトキナクリドン、メルカプトジオキ
サジン、メルカプト銅フタロシアニン、メルカプトアン
トラキノン等が挙げられる。Hereinafter, the present invention will be described in detail. The pigment dispersant of the present invention is an aqueous acrylic polymer using an organic dye or a chain transfer agent having a heterocycle. Examples of the chain transfer agent having an organic dye include, for example, phthalocyanine-based, insoluble azo-based, azo lake-based, anthraquinone-based, quinacridone-based, dioxazine-based, diketopyrrolopyrrole-based, anthrapyridine-based, insanthuron-based, indanthane There are ron series, flavanthrone series, perinone series, perylene series, thioindigo series and the like. Examples of compounds having a heterocycle include thiophene, furan, xanthene, pyrrole, imidazole, isoindoline, isoindolinone, benzimidazolone, indole, quinoline, carbazole, acridine, acridone and anthraquinone. Organic dye and /
Alternatively, the chain transfer agent having a heterocycle is an organic dye and -SH.
Or a compound having a heterocycle and -SH, and examples thereof include mercaptoquinacridone, mercaptodioxazine, mercapto copper phthalocyanine, and mercaptoanthraquinone.
【００１１】本発明の顔料分散剤は、上記のような有機
色素あるいは複素環を有する連鎖移動剤を用いて、ラジ
カル重合性不飽和結合を有する単量体を重合してなるも
のであり、アクリル系重合体の末端にのみ有機色素およ
び／または複素環を有する。本発明の顔料分散剤は、重
量平均分子量は３０００〜１０００００、酸価は１〜１
００が好ましく、顔料分散系で溶解もしくは分散してい
れば良いものである。ラジカル重合性不飽和結合を有す
る単量体としては、（メタ）アクリル酸、クロトン酸、
マレイン酸、フマル酸、シトラコン酸、イタコン酸等の
α，β−エチレン性不飽和カルボン酸、ｐ−ビニルベン
ゼンスルホン酸、２−アクリルアミドプロパンスルホン
酸等のスルホン酸基含有不飽和単量体などが挙げられ
る。また、塩基性基含有の単量体の例としては、Ｎ，Ｎ
−ジメチルアミノエチル（メタ）アクリレート、Ｎ，Ｎ
−ジエチルアミノエチル（メタ）アクリレート、Ｎ，Ｎ
−ジメチルアミノエチル（メタ）アクリルアミド、Ｎ，
Ｎ−ジエチルアミノエチル（メタ）アクリルアミドなど
が挙げられる。水酸基含有の単量体の例としては、２−
ヒドロキシエチル（メタ）アクリレート、ヒドロキシプ
ロピル（メタ）アクリレートなどが挙げられる。その他
の単量体の例としては、（メタ）アクリル酸アルキルエ
ステル類、ビニル芳香族化合物などが使用でき、具体的
に（メタ）アクリル酸アルキルエステルの例としては、
（メタ）アクリル酸メチル、（メタ）アクリル酸エチ
ル、（メタ）アクリル酸プロピル、（メタ）アクリル酸
ブチル、（メタ）アクリル酸ヘキシル、（メタ）アクリ
ル酸−２−エチルヘキシル、（メタ）アクリル酸ラウリ
ル等が挙げられる。また、ビニル芳香族化合物の例とし
ては、スチレン、α−メチルスチレン、スチレンスルホ
ン酸、ビニルトルエン、ｐ−クロルスチレン等が挙げら
れる。また、その他アクリロニトリル、酢酸ビニル等が
使用できる。The pigment dispersant of the present invention is obtained by polymerizing a monomer having a radical-polymerizable unsaturated bond using the above organic dye or a chain transfer agent having a heterocyclic ring, The organic dye and / or the heterocycle are present only at the ends of the polymer. The pigment dispersant of the present invention has a weight average molecular weight of 3,000 to 100,000 and an acid value of 1 to 1.
00 is preferable, as long as it is dissolved or dispersed in the pigment dispersion system. Examples of the monomer having a radical-polymerizable unsaturated bond include (meth) acrylic acid, crotonic acid,
Α, β-ethylenically unsaturated carboxylic acids such as maleic acid, fumaric acid, citraconic acid and itaconic acid, sulfonic acid group-containing unsaturated monomers such as p-vinylbenzenesulfonic acid and 2-acrylamidopropanesulfonic acid Can be mentioned. Examples of the basic group-containing monomer include N, N
-Dimethylaminoethyl (meth) acrylate, N, N
-Diethylaminoethyl (meth) acrylate, N, N
-Dimethylaminoethyl (meth) acrylamide, N,
N-diethylaminoethyl (meth) acrylamide etc. are mentioned. Examples of the hydroxyl group-containing monomer include 2-
Examples thereof include hydroxyethyl (meth) acrylate and hydroxypropyl (meth) acrylate. As examples of other monomers, (meth) acrylic acid alkyl esters, vinyl aromatic compounds and the like can be used. Specifically, as examples of (meth) acrylic acid alkyl ester,
Methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, (meth) acrylic acid Examples include lauryl and the like. Examples of vinyl aromatic compounds include styrene, α-methylstyrene, styrenesulfonic acid, vinyltoluene, p-chlorostyrene and the like. In addition, acrylonitrile, vinyl acetate, etc. can be used.
【００１２】前記単量体のラジカル重合は、従来から公
知の方法、例えば、反応温度としては約５０℃〜２２０
℃、重合溶媒としては、セロソロブ系溶媒、カルビトー
ル系溶剤、グライム系溶媒、セロソルブアセテート系溶
媒、アルコール系溶媒、芳香族炭化水素系溶媒、ケトン
系溶媒、エーテル系溶媒、水などがあり、これらの単独
溶媒あるいは混合系を挙げることができる。The radical polymerization of the above-mentioned monomer is a conventionally known method, for example, the reaction temperature is about 50 ° C to 220 ° C.
As the polymerization solvent, there are cellosolve type solvents, carbitol type solvents, glyme type solvents, cellosolve acetate type solvents, alcohol type solvents, aromatic hydrocarbon type solvents, ketone type solvents, ether type solvents, water, etc. The single solvent or the mixed system can be mentioned.
【００１３】本発明の顔料分散剤は、一般に市販されて
いる顔料に優れた分散効果を発揮する。例えば、可溶性
および不溶性アゾ顔料、縮合アゾ顔料等のアゾ系顔料、
フタロシアニン系顔料、キナクリドン系顔料、イソイン
ドリノン系顔料、ペリレン・ペリノン系顔料、ジオキサ
ジン系顔料、アントラキノン系顔料、ジケトピロロピロ
ール系顔料、アンスラピリミジン系顔料、アンサンスロ
ン系顔料、インダンスロン系顔料、フラバンスロン系顔
料、チオインジゴ系顔料等の有機顔料および、カーボン
ブラック、酸化チタン、黄鉛、カドミウムエロー、カド
ミウムレッド、弁柄、鉄黒、亜鉛華、紺青、群青等の無
機顔料に用いることができる。本発明の顔料分散剤の顔
料に対する配合は、顔料１００重量部に対し、０．５〜
１００重量部が好ましい。０．５重量部より少ないと顔
料分散効果が小さく好ましくない。また、１００重量部
より多く用いても用いた分の効果が得られなく塗膜性能
に悪影響を及ぼす。The pigment dispersant of the present invention exhibits an excellent dispersing effect on pigments which are generally commercially available. For example, soluble and insoluble azo pigments, azo pigments such as condensed azo pigments,
Phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, perylene / perinone pigments, dioxazine pigments, anthraquinone pigments, diketopyrrolopyrrole pigments, anthrapyrimidine pigments, ansanthrone pigments, indanthrone pigments , Organic pigments such as flavanthron-based pigments and thioindigo-based pigments, and inorganic pigments such as carbon black, titanium oxide, yellow lead, cadmium yellow, cadmium red, rouge, iron black, zinc white, navy blue, ultramarine it can. The content of the pigment dispersant of the present invention in the pigment is 0.5 to 100 parts by weight of the pigment.
100 parts by weight is preferred. If the amount is less than 0.5 parts by weight, the effect of dispersing the pigment is small, which is not preferable. Further, even if it is used in an amount of more than 100 parts by weight, the effect of the used amount cannot be obtained and the coating film performance is adversely affected.
【００１４】本発明の非水系顔料分散体に使用される非
水系樹脂としては、ライムロジンワニス、ポリアミド樹
脂、塩化ビニル樹脂、常温もしくは焼き付け塗料に用い
られるニトロセルロースラッカー、アミノアルキッド樹
脂、アクリルラッカー、アミノアクリル樹脂、ウレタン
系樹脂等が挙げられる。Examples of the non-aqueous resin used in the non-aqueous pigment dispersion of the present invention include lime rosin varnish, polyamide resin, vinyl chloride resin, nitrocellulose lacquer, aminoalkyd resin, acrylic lacquer used at room temperature or baking paint. Examples include amino acrylic resins and urethane resins.
【００１５】非水系樹脂の使用量は、顔料１００重量部
に対して固形分換算で５〜５００重量部が好ましい。特
に、濃縮分散体として使用する場合、顔料１００重量部
に対して非水系樹脂が固形分換算で５〜２００重量部が
好ましく、塗料または印刷インキとして使用する場合
は、顔料１００重量部に対して非水系樹脂が固形分換算
で１００〜５００重量部が好ましい。顔料１００重量部
に対して非水系樹脂が５重量部より少ないと顔料が分散
しにくくなり、５００重量部より多いと着色が低いため
塗料または印刷インキとしての使用に適さない場合があ
る。なお、塗料または印刷インキとして使用する場合に
は、メラミン樹脂等の硬化剤樹脂や硬化触媒、界面活性
剤等を添加しても良い。The amount of the non-aqueous resin used is preferably 5 to 500 parts by weight in terms of solid content based on 100 parts by weight of the pigment. In particular, when used as a concentrated dispersion, the non-aqueous resin is preferably 5 to 200 parts by weight in terms of solid content based on 100 parts by weight of the pigment, and when used as a paint or a printing ink, based on 100 parts by weight of the pigment. The non-aqueous resin is preferably 100 to 500 parts by weight in terms of solid content. If the amount of the non-aqueous resin is less than 5 parts by weight with respect to 100 parts by weight of the pigment, the pigment becomes difficult to disperse. When used as a paint or a printing ink, a curing agent resin such as a melamine resin, a curing catalyst, a surfactant or the like may be added.
【００１６】本発明の非水系顔料分散体は、以下のよう
な方法で製造することができる。 １．顔料と顔料分散剤を予め混合して得られる顔料組成
物を、非水系ビヒクル（すなわち、非水系樹脂および溶
媒）中に添加して分散する。 ２．非水系ビヒクルに顔料と顔料分散剤を添加して分散
する。 ３．非水系ビヒクルに顔料と顔料分散剤を予め別々に分
散し、得られた分散体を混合する。この場合、顔料分散
剤は溶剤のみで分散しても良い。 ４．非水系ビヒクルに顔料を分散した後、得られた顔料
分散体に顔料分散剤を添加する。 等の方法があり、これらのいずれによっても目的とする
効果が得られる。The non-aqueous pigment dispersion of the present invention can be manufactured by the following method. 1. A pigment composition obtained by previously mixing a pigment and a pigment dispersant is added to and dispersed in a non-aqueous vehicle (that is, a non-aqueous resin and a solvent). 2. A pigment and a pigment dispersant are added to a non-aqueous vehicle and dispersed. 3. The pigment and the pigment dispersant are previously dispersed separately in a non-aqueous vehicle, and the resulting dispersion is mixed. In this case, the pigment dispersant may be dispersed only with the solvent. 4. After dispersing the pigment in the non-aqueous vehicle, a pigment dispersant is added to the obtained pigment dispersion. The desired effects can be obtained by any of these methods.
【００１７】顔料組成物の調製法としては、顔料粉末と
本発明の非水系用顔料分散剤を単に混合しても十分な分
散効果が得られるが、ニーダー、ロール、アトライタ
ー、スーパーミル、各種粉砕機、分散機等により機械的
に混合するか、顔料の水または有機溶媒によるサスペン
ジョン系に本発明の非水系用顔料分散剤を含む溶液を添
加し、顔料表面に顔料分散剤を沈着させるか、硫酸等の
強い溶解力を持つ溶媒に有機顔料と顔料分散剤を共溶解
して水等の貧溶媒により共沈させる等の混合法を行え
ば、更に良好な結果を得ることができる。また、非水系
ビヒクル、あるいは溶剤中への顔料または顔料分散剤の
分散、混合等に、分散機としてディゾルバー、ハイスピ
ードミキサー、ホモミキサー、ニーダー、ロールミル、
サンドミル、アトライター等を使用することにより顔料
の良好な分散ができる。The pigment composition can be prepared by simply mixing the pigment powder and the non-aqueous pigment dispersant of the present invention to obtain a sufficient dispersing effect. However, kneaders, rolls, attritors, super mills, various types, etc. Whether to mechanically mix with a crusher, a disperser or the like, or to add a solution containing the non-aqueous pigment dispersant of the present invention to a suspension system of water or an organic solvent for the pigment to deposit the pigment dispersant on the pigment surface. Even better results can be obtained by a mixing method such as co-dissolving an organic pigment and a pigment dispersant in a solvent having a strong dissolving power such as sulfuric acid and coprecipitating with a poor solvent such as water. Further, a non-aqueous vehicle, or for dispersing or mixing a pigment or a pigment dispersant in a solvent, as a disperser, a dissolver, a high speed mixer, a homomixer, a kneader, a roll mill,
The pigment can be well dispersed by using a sand mill or an attritor.
【００１８】[0018]
【実施例】以下、本発明を実施例に基づいて説明する。
例中、「部」「％」は、それぞれ「重量部」「重量％」
をそれぞれ表す。EXAMPLES The present invention will be described below based on examples.
In the examples, “parts” and “%” are “parts by weight” and “% by weight”, respectively.
Respectively.
【００１９】製造例１ 温度計、攪拌装置、還流冷却管、窒素ガス導入管を備え
た四つ口フラスコに、ブチルカルビトール３５０部を仕
込み、１１０℃に加熱した。次に、 アクリル酸 ３部 アクリル酸エチル １１３部 メタクリル酸メチル １０１部 酢酸ビニル ２５部 の混合物と、 ＡＩＢＮ（大塚化学製） ４部 メルカプトアントラキノン ２５部 ブチルカルビトール ２００部 の混合物を窒素ガスを導入しながら約２時間かけて滴下
した。更に、同温度に保ちながら２時間反応させ、アン
トラキノン末端のポリマー溶液を得た。このポリマーの
重量平均分子量は４０００、酸価は１０ｍｇ・ＫＯＨ／
ｇであった。未反応物および溶媒を除去し、化合物
（ａ）２４８部を含むペーストを得た。Production Example 1 350 parts of butyl carbitol were charged into a four-necked flask equipped with a thermometer, a stirrer, a reflux condenser and a nitrogen gas inlet tube, and heated to 110 ° C. Next, a mixture of 3 parts of acrylic acid, 113 parts of ethyl acrylate, 101 parts of methyl methacrylate, 25 parts of vinyl acetate, and 4 parts of AIBN (manufactured by Otsuka Chemical Co., Ltd.), 4 parts of mercaptoanthraquinone, and 200 parts of butylcarbitol were introduced with nitrogen gas. While dropping, it took about 2 hours. Further, the reaction was carried out for 2 hours while maintaining the same temperature to obtain an anthraquinone-terminated polymer solution. This polymer has a weight average molecular weight of 4000 and an acid value of 10 mg · KOH /
g. Unreacted materials and solvent were removed to obtain a paste containing 248 parts of compound (a).
【００２０】製造例２ 温度計、攪拌装置、還流冷却管、窒素ガス導入管を備え
た四つ口フラスコに、ブチルカルビトール３５０部を仕
込み、１１０℃に加熱した。次に、 アクリル酸 １０部 アクリル酸エチル １１３部 メタクリル酸メチル １０１部 酢酸ビニル ２５部 の混合物と、 ＡＩＢＮ（大塚化学製） ２部 メルカプトアントラキノン ８．１部 ブチルカルビトール １００部 の混合物を窒素ガスを導入しながら約２時間かけて滴下
した。更に、同温度に保ちながら２時間反応させ、アン
トラキノン末端のポリマー溶液を得た。このポリマーの
重量平均分子量は１００００、酸価は３０ｍｇ・ＫＯＨ
／ｇであった。未反応物および溶媒を除去し、化合物
（ｂ）２３３．２部を含むペーストを得た。Production Example 2 350 parts of butyl carbitol was charged into a four-necked flask equipped with a thermometer, a stirrer, a reflux condenser and a nitrogen gas inlet tube, and heated to 110 ° C. Next, a mixture of acrylic acid 10 parts, ethyl acrylate 113 parts, methyl methacrylate 101 parts, vinyl acetate 25 parts, and AIBN (manufactured by Otsuka Chemical Co., Ltd.) 2 parts mercaptoanthraquinone 8.1 parts butyl carbitol 100 parts was added with nitrogen gas. While introducing, the solution was added dropwise over about 2 hours. Further, the reaction was carried out for 2 hours while maintaining the same temperature to obtain an anthraquinone-terminated polymer solution. This polymer has a weight average molecular weight of 10,000 and an acid value of 30 mg.KOH.
/ G. Unreacted materials and solvent were removed to obtain a paste containing 233.2 parts of compound (b).
【００２１】製造例３ 製造例１のメルカプトアントラキノンを２５部をメルカ
プトキナクリドン３５．８部に変えて重合した後、未反
応物および溶媒を除去し、化合物（ｃ）２５０部を含む
ペーストを得た。Production Example 3 After polymerizing 25 parts of the mercaptoanthraquinone of Production Example 1 into 35.8 parts of mercaptoquinacridone, the unreacted substances and the solvent were removed to obtain a paste containing 250 parts of the compound (c). .
【００２２】製造例４ 製造例１のメルカプトアントラキノンを２５部をメルカ
プト銅フタロシアニン６３．３部に変えて重合した後、
未反応物および溶媒を除去し、化合物（ｄ）２７８部を
含むペーストを得た。Production Example 4 After polymerizing 25 parts of the mercaptoanthraquinone of Production Example 1 to 63.3 parts of mercaptocopper phthalocyanine, polymerization was carried out,
Unreacted materials and solvent were removed to obtain a paste containing 278 parts of compound (d).
【００２３】製造例５ 製造例２のメルカプトアントラキノンを８．１部をメル
カプトキナクリドン１０．５部に変えて重合した後、未
反応物および溶媒を除去し、化合物（ｅ）２３５部を含
むペーストを得た。Production Example 5 After polymerizing 8.1 parts of the mercaptoanthraquinone of Production Example 2 into 10.5 parts of mercaptoquinacridone, the unreacted substances and the solvent were removed, and a paste containing 235 parts of compound (e) was obtained. Obtained.
【００２４】製造例６ 製造例２のメルカプトアントラキノンを８．１部をメル
カプト銅フタロシアニン２０．５部に変えて重合した
後、未反応物および溶媒を除去し、化合物（ｆ）２４４
部を含むペーストを得た。Production Example 6 After polymerizing 8.1 parts of the mercaptoanthraquinone of Production Example 2 into 20.5 parts of mercapto copper phthalocyanine, the unreacted substances and the solvent were removed to obtain the compound (f) 244.
A paste containing parts was obtained.
【００２５】製造例７ 製造例２のメルカプトアントラキノンを８．１部をメル
カプトジオキサジン２１．０部に変えて重合した後、未
反応物および溶媒を除去し、化合物（ｇ）２４５部を含
むペーストを得た。Production Example 7 After polymerizing 8.1 parts of the mercaptoanthraquinone of Production Example 2 into 21.0 parts of mercaptodioxazine, the unreacted substances and the solvent were removed, and a paste containing 245 parts of the compound (g). Got
【００２６】実施例１〜１５、比較例１〜７ 表１のように、顔料、製造例にて合成した化合物、アル
キッド樹脂（日立化成工業（株）製「フタルキッド１３
３−６０」）及びキシレンを配合し、分散した後にメラ
ミン樹脂（三井サイテック（株）製「ユーバン２０ＳＥ
６０」）を配合して、アミノアルキッド塗料を得た。各
塗料の粘度を測定したところ、表１に示したように本発
明によるものの方が比較例よりもチクソ性（ＴＩ値）が
小さく、優れた流動性を示した。また、上記塗料をフォ
ードカップ＃４で２０秒となるように粘度調整し、中塗
りした塗板（予めプライマー塗料を塗装し、水研ぎした
鋼板）に乾燥塗膜の厚さが約３０μｍとなるようにエア
ースプレーで塗装し、１０分間静置した後、１４０℃で
３０分間焼き付けた。表１に示すように、塗膜光沢にお
いても本発明によるものの方が比較例よりも優れてい
た。また、非集合性、非結晶性については、実用上特に
問題となる色分かれ安定性によって評価した。塗料を酸
化チタンのベース塗料で顔料と酸化チタンの比率が１／
１０になるようにカットし、淡色塗料を調整する。つい
でキシレンで希釈し、粘度を調整した後に試験管に注入
してガラス壁面の変化を観察すると本発明によるものの
方が比較例よりも経時による色分かれが少なかった。Examples 1 to 15 and Comparative Examples 1 to 7 As shown in Table 1, pigments, compounds synthesized in Production Examples, and alkyd resins ("Phtalkid 13" manufactured by Hitachi Chemical Co., Ltd.).
3-60 ”) and xylene are mixed and dispersed, and then melamine resin (“ Uban 20SE ”manufactured by Mitsui Cytec Co., Ltd.)
60 ") was blended to obtain an aminoalkyd paint. When the viscosity of each paint was measured, as shown in Table 1, the one according to the present invention had smaller thixotropy (TI value) than the comparative example, and showed excellent fluidity. In addition, the viscosity of the above paint was adjusted with a Ford cup # 4 for 20 seconds, and an intermediate coated plate (a steel plate preliminarily coated with a primer paint and water-polished) had a dry coating film thickness of about 30 μm. It was painted with air spray, left standing for 10 minutes, and then baked at 140 ° C. for 30 minutes. As shown in Table 1, the coating film gloss of the present invention was also superior to that of the comparative example. In addition, non-aggregation and non-crystallinity were evaluated based on color separation stability, which is particularly problematic in practical use. The paint is a titanium oxide base paint and the ratio of pigment to titanium oxide is 1 /
Cut to 10 and adjust the light color paint. Then, when diluted with xylene and adjusted in viscosity and then injected into a test tube and observed the change of the glass wall surface, the one according to the present invention showed less color separation over time than the comparative example.
【００２７】[0027]
【表１】 [Table 1]
【００２８】[0028]
【発明の効果】本発明により、インキおよび塗料などの
顔料分散液において、非集合性、流動性などの使用適性
および、塗布物の色調の鮮明性、光沢などを著しく向上
させることができた。INDUSTRIAL APPLICABILITY According to the present invention, in pigment dispersions such as inks and paints, the suitability for use such as non-aggregation and fluidity, the sharpness of the color tone of the coating, and the gloss can be remarkably improved.
Claims (3)
連鎖移動剤を用いることにより得られる、アクリル系重
合体の末端にのみ有機色素および／または複素環を有す
ることを特徴とする非水系用顔料分散剤。1. A non-aqueous pigment, which is obtained by using an organic dye and / or a chain transfer agent having a heterocycle and has an organic dye and / or a heterocycle only at the terminal of an acrylic polymer. Dispersant.
分散剤からなる顔料組成物。2. A pigment composition comprising a pigment and the non-aqueous pigment dispersant according to claim 1.
剤および非水系樹脂からなる非水系顔料分散体。3. A non-aqueous pigment dispersion comprising a pigment, the non-aqueous pigment dispersant according to claim 1 and a non-aqueous resin.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7238165A JPH0977994A (en) | 1995-09-18 | 1995-09-18 | Pigment dispersant for nonaqueous system, pigment composition containing the same, and nonaqueous pigment dispersion |
| EP96114490A EP0763378A3 (en) | 1995-09-11 | 1996-09-10 | Non-aqueous type pigment dispersing agent, composition containing thereof, and non-aqueous pigment dispersion |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7238165A JPH0977994A (en) | 1995-09-18 | 1995-09-18 | Pigment dispersant for nonaqueous system, pigment composition containing the same, and nonaqueous pigment dispersion |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0977994A true JPH0977994A (en) | 1997-03-25 |
Family
ID=17026159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7238165A Pending JPH0977994A (en) | 1995-09-11 | 1995-09-18 | Pigment dispersant for nonaqueous system, pigment composition containing the same, and nonaqueous pigment dispersion |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0977994A (en) |
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| WO2015033814A1 (en) | 2013-09-06 | 2015-03-12 | 富士フイルム株式会社 | Colored composition, cured film, color filter, color-filter manufacturing method, solid-state imaging element, image display device, polymer, and xanthene dye |
| WO2021039205A1 (en) | 2019-08-29 | 2021-03-04 | 富士フイルム株式会社 | Composition, film, near-infrared cut-off filter, pattern formation method, laminate, solid-state imaging element, infrared sensor, image display device, camera module and compound |
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