JPH0778085B2 - Method for producing emulsion-polymerized latex - Google Patents
Method for producing emulsion-polymerized latexInfo
- Publication number
- JPH0778085B2 JPH0778085B2 JP2304486A JP2304486A JPH0778085B2 JP H0778085 B2 JPH0778085 B2 JP H0778085B2 JP 2304486 A JP2304486 A JP 2304486A JP 2304486 A JP2304486 A JP 2304486A JP H0778085 B2 JPH0778085 B2 JP H0778085B2
- Authority
- JP
- Japan
- Prior art keywords
- water
- pigment
- cloud point
- soluble polymer
- polymerized latex
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 239000004816 latex Substances 0.000 title claims description 11
- 229920000126 latex Polymers 0.000 title claims description 11
- 239000000049 pigment Substances 0.000 claims description 30
- 239000000126 substance Substances 0.000 claims description 18
- 239000002245 particle Substances 0.000 claims description 17
- 229920000642 polymer Polymers 0.000 claims description 16
- 229920003169 water-soluble polymer Polymers 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 6
- 239000006185 dispersion Substances 0.000 claims description 5
- 239000003505 polymerization initiator Substances 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 239000012860 organic pigment Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 description 10
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- -1 For example Substances 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 239000001054 red pigment Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000001052 yellow pigment Substances 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 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 description 1
- 239000000693 micelle Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229940099800 pigment red 48 Drugs 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明は、電子写真などに用いられる単分散重合体微粉
末を得るための乳化重合ラテックスの製造方法に関す
る。TECHNICAL FIELD The present invention relates to a method for producing an emulsion-polymerized latex for obtaining a monodisperse polymer fine powder used in electrophotography and the like.
従来の技術 従来、顔料粒子をポリマー粒子内部に含有する乳化重合
ラテックスの製造方法においては、顔料の表面をシラン
カップリング剤、チタネートカップリング剤などにより
表面処理を施した後に重合反応を行う方法、あるいはポ
リマー、顔料、溶剤間の相互作用を利用してポリマーを
顔料表面に吸着させた後、固化する方法等が用いられて
いた。Conventional technology Conventionally, in a method for producing an emulsion polymerization latex containing pigment particles inside polymer particles, a method of performing a polymerization reaction after subjecting the surface of the pigment to a silane coupling agent, a titanate coupling agent, or the like, Alternatively, a method has been used in which the polymer is adsorbed on the surface of the pigment by utilizing the interaction between the polymer, the pigment, and the solvent, and then solidified.
発明が解決しようとする問題点 しかしながら、前者の方法においては、顔料粒子を均一
に分散させることは困難であり、後者の方法において
は、顔料を被覆するポリマーの厚みなどを制御すること
が困難であり、又溶剤を使用することによる欠点など、
種々の問題点を有するものであった。Problems to be Solved by the Invention However, in the former method, it is difficult to uniformly disperse the pigment particles, and in the latter method, it is difficult to control the thickness of the polymer coating the pigment. Yes, and the drawbacks of using a solvent,
It had various problems.
本発明は、これら従来の方法における問題点を解決する
ことを目的としてなされたものである。The present invention has been made for the purpose of solving the problems in these conventional methods.
すなわち、本発明の目的は、顔料分散性の良好な顔料粒
子を、ポリマー粒子内部に含有する乳化重合ラテックス
の製造方法を提供することにある。That is, an object of the present invention is to provide a method for producing an emulsion-polymerized latex containing pigment particles having good pigment dispersibility inside polymer particles.
本発明の他の目的は、得られた重合体微粉末を電子写真
現像剤として用いた場合、顔料による帯電性への悪影響
のない重合体微粉末を得るための製造方法を提供するこ
とにある。Another object of the present invention is to provide a production method for obtaining a polymer fine powder that does not adversely affect the charging property of the pigment when the obtained polymer fine powder is used as an electrophotographic developer. .
問題点を解決するための手段及び作用 本発明の目的は、有機顔料を水中に分散させ、該分散液
に重合開始剤及びビニル単量体を加えた後、重合を行う
ことよりなる顔料をポリマー粒子内部に含有する乳化重
合ラテックスの製造方法において、該有機顔料として、
曇点を有する水溶性高分子物質の水溶液中に分散して曇
点以上に加熱処理することによって得られた、表面に水
溶性高分子物質が吸着されものを使用することによって
達成された。Means and Actions for Solving Problems An object of the present invention is to disperse an organic pigment in water, add a polymerization initiator and a vinyl monomer to the dispersion, and then polymerize the pigment. In the method for producing an emulsion-polymerized latex contained inside particles, as the organic pigment,
It was achieved by using a substance obtained by dispersing a water-soluble polymer substance having a cloud point in an aqueous solution and heat-treating it to a temperature not lower than the cloud point and adsorbing the water-soluble polymer substance on the surface.
本発明の製造方法において、曇点とは、水溶性高分子物
質の水溶液を加熱していったときに、初めて溶液に曇り
を生じる温度を指す。曇点以下の温度においては、水溶
性高分子物質は、水溶液中で水分子と水和状態にあり、
ほぼ単分子分散の形態を取っているが、温度の上昇によ
り、水溶性高分子物質は脱水和し、巨大ミセルを生成
し、溶液に曇りを生じる。この際、水溶性高分子物質の
水溶液に、顔料粒子などの不純物が添加されていると、
顔料粒子表面に脱水和した多量の水溶性物質が吸着さ
れ、顔料粒子を取り巻く。この際、もしも水溶性高分子
物質の水溶液が曇点を有しないか、あるいは曇点以下の
温度において処理を行うと、上記した現象は見られず、
わずかな量の水溶性高分子物質が、顔料表面に付着した
だけとなる。本発明は、この様な水溶性高分子物質の水
溶液の曇点付近の挙動に着目し、本発明を完成させた。
従って、本発明の製造方法において、顔料に対し吸着作
用を示す水溶性高分子物質は、曇点を有するものでなく
てはならない。さらには、吸着処理段階において、水溶
性高分子物質の水溶液は、曇点以上に加熱される必要が
ある。In the production method of the present invention, the cloud point refers to a temperature at which a solution becomes cloudy for the first time when an aqueous solution of a water-soluble polymer substance is heated. At temperatures below the cloud point, the water-soluble polymeric substance is in a hydrated state with water molecules in the aqueous solution,
Although it is in the form of almost monomolecular dispersion, the water-soluble polymer substance is dehydrated by the increase in temperature to form giant micelles, and the solution becomes cloudy. At this time, if impurities such as pigment particles are added to the aqueous solution of the water-soluble polymer substance,
A large amount of the dehydrated water-soluble substance is adsorbed on the surface of the pigment particles and surrounds the pigment particles. At this time, if the aqueous solution of the water-soluble polymer does not have a cloud point, or if the treatment is performed at a temperature below the cloud point, the above phenomenon is not observed,
Only a small amount of water-soluble polymeric substance is attached to the surface of the pigment. The present invention has completed the present invention, focusing on the behavior near the cloud point of such an aqueous solution of a water-soluble polymer substance.
Therefore, in the production method of the present invention, the water-soluble polymer substance that exhibits an adsorption effect on the pigment must have a cloud point. Further, in the adsorption treatment step, the aqueous solution of the water-soluble polymer substance needs to be heated to the cloud point or higher.
上記の顔料表面に付着した水溶性高分子物質は、本発明
の製造方法における重合過程において、水溶性高分子物
質を吸着した顔料粒子を水に再分散させ、ビニル単量体
及び重合開始剤を添加した時点において、顔料の分散安
定剤としての役割を果たすと共に、顔料粒子表面での重
合で生成するポリマーと顔料間の接着性を高める働きを
するものと考えられる。The water-soluble polymer substance attached to the surface of the above-mentioned pigment, in the polymerization process in the production method of the present invention, the pigment particles adsorbing the water-soluble polymer substance are redispersed in water, and a vinyl monomer and a polymerization initiator are added. It is considered that, when added, it plays a role as a dispersion stabilizer for the pigment and enhances the adhesiveness between the polymer formed by polymerization on the pigment particle surface and the pigment.
本発明に用いられる水溶性高分子物質の水溶液として
は、曇点を有するものならば特に制限はないが、分散媒
として水を用いることから、通常25℃〜95℃の範囲に曇
点を有するものであるのが好ましい。上記水溶性高分子
物質の水溶液を形成し得る水溶性高分子物質としては、
例えば、ポリビニルアルコール（鹸化度が80モル％のも
の、曇点55〜60℃）、ヒドロキシプロピルセルロース
（曇点70〜80℃）、ヒドロキシプロピルメチルセルロー
ス（曇点70℃）、ポリオキシエチレン（HLBが13のも
の、曇点55〜85℃）などがあげられる。The aqueous solution of the water-soluble polymer used in the present invention is not particularly limited as long as it has a cloud point, but since water is used as the dispersion medium, it usually has a cloud point in the range of 25 ° C to 95 ° C. It is preferably one. As the water-soluble polymer substance capable of forming an aqueous solution of the water-soluble polymer substance,
For example, polyvinyl alcohol (with a saponification degree of 80 mol%, cloud point 55-60 ° C), hydroxypropyl cellulose (cloud point 70-80 ° C), hydroxypropylmethyl cellulose (cloud point 70 ° C), polyoxyethylene (HLB 13 things, cloud point 55 ~ 85 ℃) and so on.
顔料としては、カーボンブラック、黒鉛などの黒色顔
料、C.I.ピグメント イエロー１、同３、同74、同97、
同98等のアセト酢酸アリールアミド系モノアゾ黄色顔
料、C.I.ピグメント イエロー12、同13、同14等のアセ
ト酢酸アリールアミド系ジスアゾ黄色顔料、C.I.ピグメ
ント レッド48、同49:1、同53:1、同57:1、同81、同12
2、同５等の赤色もしくは紅色顔料、C.I.ピグメント
ブルー15:3等の銅フタロシアニン及びその誘導体、変性
体などの青色顔料、その他の着色の用途で用いられる周
知の染顔料が使用可能である。As pigments, black pigments such as carbon black and graphite, CI Pigment Yellow 1, 3, 3, 74, 97,
Acetoacetic acid arylamide monoazo yellow pigments such as 98, CI Pigment Yellow 12, 12, 13 and 14 etc. acetoacetic arylamide disazo yellow pigments, CI Pigment Red 48, 49: 1, 53: 1, and 57: 1, 81, 12
Red or red pigments such as 2, 5, etc., CI pigment
Copper phthalocyanine and its derivatives such as blue 15: 3, blue pigments such as modified products, and other well-known dyes and pigments used for coloring can be used.
本発明に用いられるビニル単量体としては、スチレン、
メチルスチレン、ハロゲン化スチレン等のビニル芳香族
化合物、メチルメタクリレート、エチルアクリレート、
メタクリル酸等のアクリル系ビニル単量体等があげられ
るが、これらに制限されるものではない。又、ジビニル
ベンゼン、エチレングリコールジメタクリレート等の多
官能性ビニル単量体を必要に応じて用いることができ
る。As the vinyl monomer used in the present invention, styrene,
Vinyl aromatic compounds such as methyl styrene and halogenated styrene, methyl methacrylate, ethyl acrylate,
Examples thereof include acrylic vinyl monomers such as methacrylic acid, but are not limited thereto. Further, a polyfunctional vinyl monomer such as divinylbenzene or ethylene glycol dimethacrylate can be used as necessary.
また重合開始剤としては、過硫酸カリウム、過硫酸アン
モニウム等があげられるが、これらに制限されるもので
はない。又、硫酸銅等の開裂促進剤を併用しても良い。Examples of the polymerization initiator include potassium persulfate and ammonium persulfate, but the polymerization initiator is not limited thereto. Further, a cleavage accelerator such as copper sulfate may be used together.
発明の効果 本発明の、顔料をポリマーの粒子内部に含有する乳化重
合ラテックスの製造方法においては、非常に微細な均一
粒径の粒子がラテックス状で得られ、得られた粒子は顔
料が重合体により完全にカプセル化されていることが分
った。またポリマー内部に含有されている顔料の摩擦帯
電時における電気的特性、帯電性を完全にブロックして
いることも判明した。したがって、環境依存性が極めて
少ないという特性を示す。Effects of the Invention In the method for producing an emulsion-polymerized latex containing a pigment inside the particles of a polymer according to the present invention, very fine particles having a uniform particle size are obtained in a latex form, and the obtained particles are a polymer Was found to be completely encapsulated. It was also found that the pigment contained in the polymer completely blocked the electric characteristics and the charging property during triboelectric charging. Therefore, it exhibits a characteristic of being extremely less dependent on the environment.
したがって、本発明の製造方法によって得られた乳化重
合ラテックスを電子写真現像剤等に用いた場合には、結
着樹脂中での顔料分散性を改善し、且つ、帯電性の悪影
響を防止すると言う効果を生じる。また塗料ラテックス
として使用した場合には、界面活性剤を使用することな
く、機械的安定性、耐候性等に優れた塗捲を形成する。
更に、感熱記録材料、液体現像剤、インクジェット用イ
ンクへの適用、あるいは診断試薬用担体等医療分野への
適用も可能であり、応用範囲は多岐にわたる。Therefore, when the emulsion-polymerized latex obtained by the production method of the present invention is used for an electrophotographic developer or the like, it is said that the pigment dispersibility in the binder resin is improved and the adverse effect of the charging property is prevented. Produce an effect. When it is used as a paint latex, a coating having excellent mechanical stability, weather resistance and the like is formed without using a surfactant.
Further, it can be applied to a heat-sensitive recording material, a liquid developer, an inkjet ink, or a medical field such as a diagnostic reagent carrier, and its application range is wide.
実施例 以下本発明の実施例を示すが、本発明はこれらによって
何ら限定されるものではない。EXAMPLES Examples of the present invention will be shown below, but the present invention is not limited thereto.
1000mlビーカーにポリビニルアルコール（クラレポバー
ルPVA-420H（曇点55〜60℃））の４％水溶液500ml中
に、銅フタロシアニン（SUMIKA PRINT GN−Ｏ）40gをホ
モジナイザー（5000rpm）で攪拌しながら添加した。添
加終了後、10分間攪拌を継続した。その後、1000mlセパ
ラブルフラスコに移し、温度を55℃まで昇温して15分間
攪拌を継続した。室温まで降温後、遠心分離器により２
回分離操作を行った。To a 1000 ml beaker, 40 g of copper phthalocyanine (SUMIKA PRINT GN-O) was added to 500 ml of a 4% aqueous solution of polyvinyl alcohol (Kuraray Poval PVA-420H (cloud point 55-60 ° C)) while stirring with a homogenizer (5000 rpm). After the addition was completed, stirring was continued for 10 minutes. Then, the mixture was transferred to a 1000 ml separable flask, the temperature was raised to 55 ° C., and stirring was continued for 15 minutes. After cooling to room temperature, use a centrifuge to
The separation operation was performed once.
これを再び蒸溜水450ml中のホモジナイザーによって分
散した。得られた分散物を、N2導入口、還流管、パドル
型攪拌翼を備えた1000mlセパラブルフラスコ重合器に移
し、温度を60℃に上げた。次いで過硫酸アンモニウム0.
25gを50mlの蒸溜水に溶解したものを添加した。引き続
いてエチルアクリレート40gを添加し、2.5時間重合し
た。さらに引き続いて、スチレンモノマー32g及びメチ
ルメタクリレート8gを約30分かけて添加し、さらに19時
間重合を継続した。重合終了後、粒子は完全に沈降し
た。これを遠心分離して乾燥し、走査型電子顕微鏡で観
測したところ0.05〜0.15μの球状の粒子からなっている
ことが分かった。又、ESCAによるスペクトルから、銅フ
タロシアニンがポリマーによってカプセル化されている
ことが明らかとなった。This was again dispersed by a homogenizer in 450 ml of distilled water. The obtained dispersion was transferred to a 1000 ml separable flask polymerization vessel equipped with an N 2 inlet, a reflux tube and a paddle type stirring blade, and the temperature was raised to 60 ° C. Then ammonium persulfate 0.
A solution of 25 g dissolved in 50 ml distilled water was added. Subsequently, 40 g of ethyl acrylate was added and polymerization was carried out for 2.5 hours. Subsequently, 32 g of styrene monomer and 8 g of methyl methacrylate were added over about 30 minutes, and the polymerization was continued for another 19 hours. After the completion of the polymerization, the particles were completely settled. It was centrifuged, dried, and observed with a scanning electron microscope. As a result, it was found to consist of spherical particles of 0.05 to 0.15μ. Moreover, from the spectrum by ESCA, it was revealed that the copper phthalocyanine was encapsulated by the polymer.
得られた単分散重合体微粒子をスチレン/N−スチルメタ
クリレート共重合体とともに溶融混練トナー化し、帯電
特性を調べたところ、銅フタロシアニンによる帯電性へ
の影響が完全にブロックされていることが分った。更
に、定着特性を調べたところ、充分に発色していること
が分った。The obtained monodisperse polymer particles were melt-kneaded into a toner together with a styrene / N-styryl methacrylate copolymer, and the charging characteristics were examined.The effect of copper phthalocyanine on the charging property was found to be completely blocked. It was Further, when the fixing property was examined, it was found that the color was sufficiently developed.
比較例 ポリマーによってカプセル化されていない銅フタロシア
ニンを用いて帯電特性を調べたところ、銅フタロシアニ
ンの影響で帯電特性が環境変化に対して不安定であっ
た。Comparative Example When the charging characteristics were investigated using copper phthalocyanine which was not encapsulated by the polymer, the charging characteristics were unstable due to the influence of copper phthalocyanine against environmental changes.
Claims (1)
合開始剤及びビニル単量体を加えた後、重合を行うこと
よりなる顔料をポリマー粒子内部に含有する乳化重合ラ
テックスの製造方法において、該有機顔料として、曇点
を有する水溶性高分子物質の水溶液中に分散して曇点以
上に加熱処理することによって得られた、表面に水溶性
高分子物質が吸着されものを使用することを特徴とする
乳化重合ラテックスの製造方法。1. A method for producing an emulsion-polymerized latex containing a pigment inside a polymer particle, which comprises dispersing an organic pigment in water, adding a polymerization initiator and a vinyl monomer to the dispersion, and then performing polymerization. In the above, as the organic pigment, used is one obtained by dispersing in a water solution of a water-soluble polymer substance having a cloud point and heat-treating the solution above the cloud point, and having the water-soluble polymer substance adsorbed on the surface. A method for producing an emulsion-polymerized latex, comprising:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2304486A JPH0778085B2 (en) | 1986-02-06 | 1986-02-06 | Method for producing emulsion-polymerized latex |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2304486A JPH0778085B2 (en) | 1986-02-06 | 1986-02-06 | Method for producing emulsion-polymerized latex |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62181302A JPS62181302A (en) | 1987-08-08 |
| JPH0778085B2 true JPH0778085B2 (en) | 1995-08-23 |
Family
ID=12099453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2304486A Expired - Lifetime JPH0778085B2 (en) | 1986-02-06 | 1986-02-06 | Method for producing emulsion-polymerized latex |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0778085B2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01237502A (en) * | 1988-03-17 | 1989-09-22 | Canon Inc | Color filter |
| US6214467B1 (en) | 1998-07-24 | 2001-04-10 | Rohm And Haas Company | Polymer-pigment composites |
| JP2007246913A (en) * | 1999-02-04 | 2007-09-27 | Mizutani Paint Co Ltd | Aqueous dispersion, method for producing the same, and coating composition |
| US7741384B2 (en) | 2006-05-11 | 2010-06-22 | Hewlett-Packard Development Company, L.P. | Encapsulation of pigment particles by polymerization |
| ES2351836B1 (en) * | 2010-09-07 | 2011-10-10 | Microlitix- Control Microbiologico Integral Slne | ADDITIVE FOR ORGANIC POLYMER MATERIALS AND / OR INORGANIC AGLOMERATES AND PROCEDURE AND CORRESPONDING USES. |
-
1986
- 1986-02-06 JP JP2304486A patent/JPH0778085B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62181302A (en) | 1987-08-08 |
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