TW200808916A - Method for dispersing pigment particles - Google Patents
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- TW200808916A TW200808916A TW095129605A TW95129605A TW200808916A TW 200808916 A TW200808916 A TW 200808916A TW 095129605 A TW095129605 A TW 095129605A TW 95129605 A TW95129605 A TW 95129605A TW 200808916 A TW200808916 A TW 200808916A
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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200808916 九、發明說明: 【發明所屬技術領域】 本發明係有關於一種能使顏料微粒分散的配方與方 法0 【先前技術】 習知顏料(pigments)係為用於製造彩色液晶(c〇1〇r-LCD) 顯示裔之顏料分散型彩色光阻劑的主要原料之一,其功能 在於決定光阻的著色與色彩化。就工業應用而言,顏料微 粒的平均粒徑大小需要在100〜200nm的範圍内。使用較小 的顏料微粒能增加顏料的色澤強度、對比,以及彩色液晶 顯不器產品的光穿透率,以提昇彩色液晶顯示器的品質。 習知用於使顏料微粒分散於液體中的方法,包含滾磨 法(roll mill)法、球磨(ball mill)法、砂磨(bead mm)法、振 金研磨法、均質法,以及雜分散機等,但這些方法均有 需較長之製程時間與研磨介質污染的缺點。 為克服前述習知技術中所存在的缺點,美國專利第仍 5,921,478號揭示-種藉由超臨界分散法將微細碳黑 (carbon black)顆粒分散至純水中的方法。於該方法中,藉 由超臨界二氧化碳的幫助,純水#2wt%^黑粉經由力曰口 壓與加熱的的步驟’自常溫常璧下升幻〇 Mpa (他料 Pascal)’、333 K。之後’再將此混合物移至爆炸粉碎槽 (eXPl〇Si〇nCmShingtank)中’㈣致均勾分散的碳黑微粒。 雖此種方法可將碳黑微粒均勻的分散至純水中,惟其僅能 5 200808916 獲致粒徑小於5μιη的分散顆粒,此並不符合工業應用上的 要求。 另有人提出一種類似的方法,以使顏料紅色177 (red Π7)、綠36 (green 36)與藍15:6 (blue 15:6)的超細微粒得以 分散於丙二醇曱醚醋酸酯(Propylene Glycol Monomethyl200808916 IX. DESCRIPTION OF THE INVENTION: 1. Field of the Invention The present invention relates to a formulation and method for dispersing pigment microparticles. [Prior Art] Conventional pigments are used to manufacture color liquid crystals (c〇1〇) r-LCD) One of the main raw materials for the display of pigment-dispersed color photoresists, whose function is to determine the color and color of the photoresist. For industrial applications, the average particle size of the pigment particles needs to be in the range of 100 to 200 nm. The use of smaller pigment particles increases the color strength and contrast of the pigment, as well as the light transmittance of the color liquid crystal display to enhance the quality of the color liquid crystal display. Conventional methods for dispersing pigment microparticles in a liquid, including a roll mill method, a ball mill method, a bead mm method, a vibrating gold grinding method, a homogenization method, and a heterodispersion method. Machines, etc., but these methods have the disadvantages of requiring a long process time and contamination of the grinding media. In order to overcome the disadvantages of the prior art, U.S. Patent No. 5,921,478 discloses a method of dispersing fine carbon black particles into pure water by supercritical dispersion. In this method, with the help of supercritical carbon dioxide, pure water #2wt%^ black powder through the pressure and pressure of the step of heating 'from normal temperature, 〇 〇 〇 Mpa (he Pascal)', 333 K . Then, the mixture was moved to an explosion pulverization tank (eXPl〇Si〇nCmShingtank) to produce carbon black particles which were uniformly dispersed. Although this method can uniformly disperse carbon black particles in pure water, it can only obtain dispersed particles having a particle size of less than 5 μm, which does not meet the requirements of industrial applications. A similar approach has been proposed to disperse ultrafine particles of pigment red 177 (red Π7), green 36 (green 36) and blue 15:6 (blue 15:6) in propylene glycol oxime ether acetate (Propylene Glycol). Monomethyl
Ether Acetate, PGMEA) t (W. T. Cheng et al, Dispersion of organic pigments using supercritical carbon dioxide, J. CW/ozW加^ 270 (2004 106_112))。惟習知提高顏料濃 度,會使得顏料的的粒徑增加,因此該方法僅能獲致〇 〇〇2 wtQ/❻的顏料濃度。而此一低濃度的顏料由於會增加工業使 用上的成本,因此該方法所得之分散顏料並不適用於工業 應用上。 口此知極研究出一種能提南顏料分散於溶劑中的濃 度,且具有工業上可應用之粒徑大小的顏料分散方法,便 成為一件即為重要的事。 【發明内容】 為了克服習知技術所遭遇之困難與問題,本發明之目 勺P在於&供種能使顏料微粒分散的配方鱼 超臨界二氧化麵幫助,可使顏料微粒得以細化並均㈣ 分散於溶劑中。 根據本發明所指出之一種顏料組合物,其加入至一溶 劑中時能使其巾所含之綱微粒分散於娜射,其包含: 一顏料的微粒;以及 200808916 與親有親顏_ 其中,該顏料相對於該顏料組合物與該溶 度為0.1〜2 wt % 為 20〜60 wt % 劑總重的濃 ’且該共聚物分散船目對於該顏料的濃度 根據本發明所指出之一 驟包含: 種分散顏料微粒的方法,其步Ether Acetate, PGMEA) t (W. T. Cheng et al, Dispersion of organic pigments using supercritical carbon dioxide, J. CW/ozW plus ^ 270 (2004 106_112)). However, it has been conventionally known that increasing the pigment concentration causes an increase in the particle size of the pigment, so that the method can only obtain a pigment concentration of 〇 2 wt Q / ❻. Since this low concentration of pigment increases the cost of industrial use, the dispersed pigment obtained by this method is not suitable for industrial applications. It has become an important matter to study a pigment dispersion method which can extract the concentration of the pigment in the solvent and has an industrially applicable particle size. SUMMARY OF THE INVENTION In order to overcome the difficulties and problems encountered by the prior art, the object of the present invention P is to provide a supercritical dioxide surface for the formulation of pigment flakes, and to refine the pigment particles. (4) Disperse in the solvent. A pigment composition according to the present invention, which is added to a solvent to disperse the particles contained in the towel in a nano-particle, comprising: a pigment particle; and 200808916 with a pro- _ The pigment is concentrated relative to the pigment composition with a solubility of 0.1 to 2 wt% of 20 to 60 wt% of the total weight of the agent and the concentration of the copolymer dispersion for the pigment is determined according to the present invention. Contains: a method of dispersing pigment particles, the steps thereof
()將顏料與具有親顏料基办)與親 溶劑基(S〇lvent-affinity)之共聚物分散劑加入至一 f劑中以形成—混合物,並將該混合物置入-分 政才曰中’其中該顏料相對於該混合物的濃度為 • 1、2 wt /〇’且邊共聚物分散劑相對於該顏料的濃 度為20〜60 wt % ; (B) 於心政槽中導人超臨界二氧化碳,使該分散槽 内壓力上升並維持於不低於1〇Μρ&,同時使該分 散槽内溫度昇溫並維持在320〜400 K; (C) 該齡物於步驟⑻條件下維持U)〜60分鐘後,迅 U睪【至大氣壓(atm()_eric以⑽職),並移至一 接收槽中。 沾、,根據本發财法4理後可使難微粒得以 100〜200nm 、γ句粒铨大小均勻的分散於溶劑中,且其濃度可達ο」〜2 ^ Μ財發明方法處理者可獲得適合卫業應用上的 =t ’且可較η’等人(職)揭示之方法所得顏料 /辰度要而約5〇〇倍。 200808916 本發明將藉由下述的詳細說明及實施例做進一步的說 明,這些實施例並不限制本發明前面所揭示之内容。熟習 本發明之技藝者,可做些許之改良與修飾,但仍不脫離本 發明之範疇。 【實施方式】 弟圖為執行本發明分散顏料微粒之方法的裝置之一 實,例的示意圖。根據本發明分散顏料微粒的方^,首先 係藉由將顏料與―具有親顏料基與親溶劑基之共聚物分 散劑加入至—溶劑中以形成一混合物,之後將其ί入一分 散槽10巾。接著,將超臨界二氧化碳自儲存桶12注入分 散=10中。前述超臨界二氧化碳可經由—過濾器14過滤 f除其中的雜質,並藉由—液體幫浦16注入分散槽⑺ 内壓if11G於注入超臨界二氧化碳後,使分散槽10槽 一^升至不低於1GMPa,更佳為lG〜4〇MPa,並維持此 測,另1分散槽10槽内的麼力可藉由一壓力計2 0進行量 揭in方面_,於注人超臨界二氧化碳懸_,同時對 κ,並输姓進订加熱’使其達320〜400 κ,更佳為328〜350 進行力埶此血度。此可藉由一加熱器18對該分散槽10 進订加熱,並:藉由-溫度計22量測其溫度。 物分^访使則述顏料、具有親顏料基與親溶劑基之共聚 形成之遇合物於上述之溫度與麼力下維 才曰此%間稱為停滯時間(holding time)。藉此可 8 200808916 使共聚物分散劑的親顏料基進入顏料顆粒中,並使其親溶 劑基位於溶劑中,以使顏料顆粒為共聚物分散劑所包覆^ 得以安定地分散於溶劑中。最後,開啟分散槽1〇與接收槽 24間的閥Η,使分散槽1G中的顏料溶液迅速釋屢至大^ 壓(常溫常壓),並將顏料分散液導入接收槽24中。藉此二 即可獲致均勻分散於溶劑中的顏料微粒,且其胃具有 100〜200nm的平均粒徑,並具有良好的安定性且能維持一 長時間。前述之停滯時間於本發明中並沒有特別的限制, 瞻但基於考量顏料顆粒的分散效果與生產效率,其較佳為 10〜60分鐘,更佳為20〜40分鐘。 別述可應用本發明方法之顏料,並沒有特別的限制, 例如酞菁類顏料(例如,銅酞菁(Cu_phthal〇cyanine,Blue 15:6))、多氯溴化銅酞菁(p〇iychl〇r〇 br〇m〇 Cu-Phthalocyanine,Green 36)、蒽醌衍生物顏料(例如,4, 4’-二氨基-1,1’_二蒽醌(4,4,-伽11^11〇-1,1,_—1^11叫1^11〇野1, Red 177)與1-苯曱醯氨基斗羥基蒽醌(Benz〇ylati〇n _ ^腿1110冰 hydroxyanthraquinone,Red 89))、稠環蒽醌衍生 物(Polycarbocyclic anthraquinone,Red 168)、吼略併u比洛二 酮顏料(Diketopyrrolopyrrole,Red 254)、異吲哚琳顏料 (Isoindoline,Yeii〇w 139)與二噁嗪顏料(以0\犯1狀, Violet 23)等,但並不僅限於此。上述顏料相對於混合物 的濃度較佳為0.1〜2 wt %,更佳為0.5〜1·5 wt %。 前述之共聚物分散劑,只要任何習知同時具有親顏料 基與親溶劑基之共聚物分散劑皆可被應用於本發明中,於 200808916 本發明中並沒有特別的限制。例如,胺改性的聚酯(Amine modified polyester)(商品化產品,例如 Hypermer LP4,ICI, Americas Inc·,US A)、聚 1旨 / 聚胺共聚物(p〇iyester/p〇iyamine copolymer)(商 on化產品’例如 Hypermer PS3, ICI,Americas() adding a pigment to a copolymer with a pro-pigmentation base and a solvent-dispersing agent to a f-agent to form a mixture, and placing the mixture in a sub-policy 'The concentration of the pigment relative to the mixture is • 1, 2 wt / 〇 ' and the concentration of the side copolymer dispersant relative to the pigment is 20 to 60 wt %; (B) Leading supercritical in the heart of the tank Carbon dioxide, the pressure in the dispersion tank is raised and maintained at not less than 1 〇Μ ρ & while the temperature in the dispersion tank is raised and maintained at 320 to 400 K; (C) the aged material is maintained under the condition of step (8). After ~60 minutes, 睪U睪[to atmospheric pressure (atm()_eric to (10) position) and move to a receiving slot. Dip, according to the method of the current financing method 4, the difficult particles can be dispersed in the solvent 100~200nm, γ sentence size uniform, and the concentration can reach ο"~2 ^ It is suitable for the application of the health industry = t ' and can be about 5 times more than the pigment obtained by the method disclosed by η' et al. The invention is further illustrated by the following detailed description and examples, which are not intended to limit the invention. A person skilled in the art can make some modifications and modifications without departing from the scope of the invention. [Embodiment] A diagram showing an example of a device for carrying out the method of dispersing pigment particles of the present invention is shown. According to the present invention, the pigment fine particles are first dispersed by adding a pigment and a copolymer dispersant having a pigment-affinity group and a solvent-soluble group to a solvent to form a mixture, which is then introduced into a dispersion tank 10 towel. Next, supercritical carbon dioxide is injected from the storage tank 12 into the dispersion = 10 . The supercritical carbon dioxide can be filtered by the filter 14 to remove impurities therein, and the liquid pump 16 is injected into the dispersion tank (7) by internal pressure if11G to inject supercritical carbon dioxide, so that the dispersion tank 10 is raised to a low level. In 1GMPa, more preferably lG~4〇MPa, and maintain this test, the force in the other 10 slots of the dispersion tank can be revealed by a pressure gauge 20, in the case of supercritical carbon dioxide suspension _ At the same time, on the κ, and lose the name to order heating ~ make it up to 320 ~ 400 κ, more preferably 328 ~ 350 to force this blood. The dispersion tank 10 can be heated by a heater 18 and the temperature is measured by a thermometer 22. The content of the pigment, the copolymer formed by the copolymerization of the pigment-affinity group and the solvent-soluble group, is called the holding time between the above-mentioned temperature and the force. Thereby, 8 200808916, the pro-pigment group of the copolymer dispersant is introduced into the pigment particles, and the lyophilic group is placed in the solvent so that the pigment particles are coated with the copolymer dispersant to be stably dispersed in the solvent. Finally, the valve 间 between the dispersion tank 1〇 and the receiving tank 24 is opened, and the pigment solution in the dispersion tank 1G is quickly released to a large pressure (normal temperature and normal pressure), and the pigment dispersion liquid is introduced into the receiving tank 24. Thereby, the pigment fine particles uniformly dispersed in the solvent can be obtained, and the stomach has an average particle diameter of 100 to 200 nm, and has good stability and can be maintained for a long time. The aforementioned stagnation time is not particularly limited in the present invention, but it is preferably from 10 to 60 minutes, more preferably from 20 to 40 minutes, based on the dispersion effect and production efficiency of the pigment particles. The pigment to which the method of the present invention can be applied is not particularly limited, and examples thereof include a phthalocyanine-based pigment (for example, Cu phthalocyanine (Blue 15: 6)), and copper phthalocyanine phthalocyanine (p〇iychl). 〇r〇br〇m〇Cu-Phthalocyanine, Green 36), anthracene derivative pigment (for example, 4, 4'-diamino-1,1'-diindole (4,4,-gamma 11^11〇) -1,1,__1^11 is called 1^11〇野1, Red 177) and 1-phenylhydrazineamino hydroxy hydrazine (Benz〇ylati〇n _ ^leg 1110 ice hydroxyanthraquinone, Red 89), Polycarbocyclic anthraquinone (Red 168), 并 并 比 比 二 二 颜料 颜料 (Diketopyrrolopyrrole, Red 254), Isoindoline (Yeindoline, Yeii〇w 139) and dioxazine pigments 0\ commits 1 shape, Violet 23), etc., but is not limited to this. The concentration of the above pigment relative to the mixture is preferably from 0.1 to 2% by weight, more preferably from 0.5 to 1.5% by weight. The above-mentioned copolymer dispersing agent can be used in the present invention as long as any of the conventional copolymer dispersing agents having both a pigment-based group and a solvent-soluble group, and is not particularly limited in the present invention. For example, Amine modified polyester (commercially available products such as Hypermer LP4, ICI, Americas Inc., US A), polyamine/polyamine copolymer (p〇iyester/p〇iyamine copolymer) (Business on products such as Hypermer PS3, ICI, Americas
Inc” USA)、聚醚胺(P〇ly〇Xyaijyiene amine)(商品化產品, 例如 Hypermer KD2, ICI,Americas Inc·,USA)、胺改性的寡 聚物(Amine modified ol〇g〇mer)(商品化產品,例如Inc" USA), polyetheramine (P〇ly〇Xyaijyiene amine) (commercial products such as Hypermer KD2, ICI, Americas Inc., USA), amine modified oligomers (Amine modified ol〇g〇mer) (commercial products, such as
Hypermer 1070, ICI,Americas Inc.,USA)、丙烯酸酯與親顏 料基之共聚物(Acrylate_Cop〇lymer with pigment affmic groups)(商品化產品,例如 Disperbyk-2050,BYK, Germany),以及親顏料基之共聚物(cop〇lymer with pigmentHypermer 1070, ICI, Americas Inc., USA), Acrylate_Cop〇lymer with pigment affmic groups (commercial products such as Disperbyk-2050, BYK, Germany), and pigment-based Copolymer (cop〇lymer with pigment
afflnic groups)(商品化產品’例如 Disperbyk-2150,BYKAfflnic groups) (commercial products such as Disperbyk-2150, BYK
Germany),但並不僅限於此。此共聚物分散劑的添加量於 本發明中並沒有特別的限制,但為獲得較佳的顏料顆粒分 散安定性效果,以顏料的質量為1時,其用量較佳為2〇〜6〇 wt %,更佳為30〜50 wt %。 前述之溶劑,只要是任何習知可供顏料顆粒分散於其 中者,皆可被應用於本發明中。在此可舉出的例子,包含 丙二醇曱醚醋酸酯(pr〇pylene Glycol Monomethyl Ether Acetate,PGMEA)、環己g同(Cyclohexanone)與 3-乙氧基丙酸 乙酯(Ethyl-3-Ethoxypropi〇nate,EEP)等,但並不僅限於此。 為使顏料更易於分散於溶劑中,前述將顏料與共聚物 分散劑加入至溶劑中形成混合物的步驟中,可進一步包含 一對該混合物進行顏料微粒預分散之步驟,此步驟只要是 200808916 任何習知可用以將顏料顆粒永久或暫時分散於溶劑中的方 法皆可應用於本發明中,例如超音波震蘯法、球磨(ball mill) 法、砂磨(bead mill)法、振盪研磨法、均質法、以及砂粒分 散機等,但並不僅限於此。 另外,為使顏料於溶劑中有更佳之分散效果及增強經 分散之顏料微粒於溶劑中的安定性,前述顏料、具有親顏 料基與親溶劑基之共聚物分散劑與溶液所形成之混合物 中,可進一步添加一親二氧化碳界面活性劑(C02-philicGermany), but not limited to this. The amount of the copolymer dispersant to be added is not particularly limited in the present invention, but in order to obtain a preferable dispersion stability of the pigment particles, when the mass of the pigment is 1, the amount thereof is preferably from 2 to 6 〇wt. %, more preferably 30~50 wt%. The foregoing solvent can be used in the present invention as long as it is any conventionally dispersible pigment particles. Examples which may be mentioned herein include pr〇pylene Glycol Monomethyl Ether Acetate (PGMEA), cyclohexanone and ethyl 3-ethoxypropionate (Ethyl-3-Ethoxypropi〇). Nate, EEP), etc., but not limited to this. In order to make the pigment more easily dispersed in the solvent, the foregoing step of adding the pigment and the copolymer dispersant to the solvent to form a mixture may further comprise a step of pre-dispersing the pigment particles with the mixture, as long as it is 200808916 It is known that any method which can be used for permanently or temporarily dispersing pigment particles in a solvent can be applied to the present invention, for example, ultrasonic shock method, ball mill method, bead mill method, oscillatory grinding method, homogenization Law, sand disperser, etc., but not limited to this. In addition, in order to have a better dispersing effect of the pigment in the solvent and enhance the stability of the dispersed pigment microparticles in the solvent, the pigment, the mixture of the disperse pigment base and the solvent-soluble copolymer dispersant and the solution are formed. , can further add a pro-carbon dioxide surfactant (C02-philic
surfactants)。做為本發明中親二氧化碳界面活性劑的例 子’包括含氟的碳氫化合物(fluorinated hydrocarbons),或 稱氟化界面活性劑(f[uorosurfactant),但並不僅限於此。做 為前述氟化界面活性劑的例子,例如具有 F(CF2CF2)nCH2CH2〇(CH2CH2〇)m 所示之化學式,其中 η-1 〜7 ’ m=(M5 (例如,Zonyl FS0100 與 Zonyl FSN-100), 或全氟丁基磺酸(perfluorobutane sulfonate,PFBS)(例如 3M™-N〇Vec-FC一4432 與 3M™_N〇vec_FCM43〇)。本發明中 親二氧化碳界面活性劑的添加量於本發財並沒有特別的 限制彳 -考昼生產成本與顏料顆粒分散效果,以顏料的質 里為1日守’其用讀佳為〇 5〜3 wt%,更佳為0.5〜2 %。 於本發明方法中,超臨界二氧化碳能快速的渗入聚集 的顏料U粒細缝巾’然後經由快速的釋壓使聚集的顏料顆 地,成微小粒子。經分散之顏料微粒的穩定性則 ^ ^刀政步^巾’使用具有親顏料基與親溶劑基之止 ^刀散·達成。經以本發明方法處理後,藉由超臨界 200808916 二氧化碳的幫助,可獲致平均粒徑大小在100〜2〇〇nm之間 的顏料微粒。 另外,本發明亦揭示一種顏料組合物,當其加入至一 溶劑中時能使其中所含之顏料微粒分散於該溶劑中,其包 含一顏料的微粒’以及一具有親顏料基(pigment-affinity) 與親溶劑基(sol vent-affinity)的共聚物分散劑。 前述之顏料,於本發明中並沒有特別的限制,例如酞 青類顏料(例如,銅狀菁(Cu-Phthalocyanine, Blue • 15:6))、多氯漠化銅酞菁(Polychloro bromoSurfactants). The example of the carbon dioxide surfactant as the present invention includes, but is not limited to, fluorinated hydrocarbons, or fluorinated surfactants (f [uorosurfactant]. As an example of the aforementioned fluorinated surfactant, for example, a chemical formula represented by F(CF2CF2)nCH2CH2〇(CH2CH2〇)m, wherein η-1 〜7 ' m=(M5 (for example, Zonyl FS0100 and Zonyl FSN-100) ), or perfluorobutane sulfonate (PFBS) (for example, 3MTM-N〇Vec-FC-4432 and 3MTM_N〇vec_FCM43〇). The amount of the carbon dioxide surfactant added in the present invention is rich in the present There is no particular limitation 彳 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 昼 颜料 颜料 颜料In the method, the supercritical carbon dioxide can rapidly infiltrate the aggregated pigment U-seam fine-slit towel, and then the aggregated pigment is grounded into fine particles through rapid pressure release. The stability of the dispersed pigment particles is ^^ ^巾' is achieved by using a pro-pigment base and a solvophilic group. After treatment by the method of the present invention, by using supercritical 200808916 carbon dioxide, the average particle size can be obtained at 100~2〇〇nm. Pigment particles between. In addition, the invention also discloses A pigment composition which, when added to a solvent, is capable of dispersing pigment microparticles contained therein in the solvent, which comprises a pigment microparticle 'and a pigment-affinity and a solvophilic group (Sol vent-affinity) copolymer dispersant. The aforementioned pigment is not particularly limited in the present invention, for example, an indigo pigment (for example, Cu-Phthalocyanine, Blue • 15:6), Polychlorine phthalocyanine (Polychloro bromo)
Cu-Phthalocyanine,Green 36)、蒽g昆衍生物顏料(例如,4, 4’-二氨基-1,Γ-二蒽g昆(4, 4’-diammo-l,Γ-dianthraquinonyl, Red 177)與1-苯曱酿氨基_4_經基蒽g昆(Benzoylation l_amino-4- hydroxyanthraquinone, Red 89))、稠環蒽西昆衍生 物(Polycarbocyclic anthraquinone,Red 168)、吼嘻併 σ比略二 酮顏料(Diketopyrrolopyrrole,Red 254)、異。引 π朵琳顏料 (Isoindoline,Yellow 139)與二噁嗪顏料(Dioxazine, 馨 Violet 23)等,但並不僅限於此。其中該顏料相對於該顏 料組合物與該溶劑總重的濃度為0.^2 wt %,且該共聚物 分散劑相對於該顏料的濃度為2〇〜60 wt %。 前述之共聚物分散劑,只要任何習知同時具有親顏料 基與親溶劑基之共聚物分散劑皆可被應用於本發明中,於 本發明中並沒有特別的限制。例如,胺改性的聚g旨(Amine modified polyester)(商品化產品,例如 Hypermer LP4, ICI, Americas Inc” USA)、聚酯/聚胺共聚物(?0匕咖6吻〇17&1^1^ 12 200808916 copolymer)(商品化產品,例如 Hypermer PS3, ICI,Americas Inc” USA)、聚醚胺(Polyoxyaljylene amine)(商品化產品, 例如 Hypermer KD2, ICI,Americas Inc” USA)、胺改性的寡 聚物(Amine modified ologomer)(商品化產品,例如 Hypermer 1070, ICI,Americas Inc” USA)、具親顏料基之丙 浠酸酯共聚物(Acrylate-Copolymer with pigment affmic groups) (商品化產品,例如Disperbyk-2050,BYK,Cu-Phthalocyanine, Green 36), 蒽g-kun derivative pigment (for example, 4, 4'-diamino-1, Γ-dimmo-l, Γ-dianthraquinonyl, Red 177) And Benzoylation l_amino-4-hydroxyanthraquinone (Red 89), Polycarbocyclic anthraquinone (Red 168), 吼嘻 and σ Ketone pigment (Diketopyrrolopyrrole, Red 254), different. Isoindoline (Yelindoline, Yellow 139) and dioxazine pigment (Dioxazine, Xin Violet 23), etc., but not limited to this. Wherein the concentration of the pigment relative to the total weight of the pigment composition and the solvent is 0.2% by weight, and the concentration of the copolymer dispersant relative to the pigment is from 2 Å to 60% by weight. The copolymer dispersant described above can be used in the present invention as long as any conventional copolymer dispersant having both a pigment-based group and a solvent-soluble group, and is not particularly limited in the present invention. For example, Amine modified polyester (commercial product such as Hypermer LP4, ICI, Americas Inc. USA), polyester/polyamine copolymer (?0匕咖6〇17&1^ 1^ 12 200808916 copolymer) (commercial products such as Hypermer PS3, ICI, Americas Inc. USA), Polyoxyaljylene amine (commercial products such as Hypermer KD2, ICI, Americas Inc. USA), amine modification Amine modified ologomer (commercial products such as Hypermer 1070, ICI, Americas Inc. USA), Acrylate-Copolymer with pigment affmic groups (commercial products) , for example, Disperbyk-2050, BYK,
Germany),以及親顏料基之團聯共聚物(Cop〇lymer wkh pigment affinic groups)(商品化產品,例如 Disperbyk_2150, BYK,Germany),但並不僅限於此。此共聚物分散劑的添 加量於本發明中並沒有特別的限制,但為獲得較佳的顏料 顆粒分散安定性效果,以顏料的質量為1時,其用量較佳 為20〜60 wt %,更佳為30〜50 wt %。 前述之溶劑,只要是任何習知可供顏料顆粒分散於其 中者,皆可被應用於本發明中。在此可舉出的例子,包含 丙二醇甲醚醋酸酯(pr〇pylene Glyc〇1 M〇nomethy][ EtherGermany), and Cop〇lymer wkh pigment affinic groups (commercial products such as Disperbyk_2150, BYK, Germany), but are not limited thereto. The amount of the copolymer dispersant to be added is not particularly limited in the present invention, but in order to obtain a preferable pigment particle dispersion stability effect, when the mass of the pigment is 1, the amount thereof is preferably from 20 to 60% by weight. More preferably 30 to 50 wt%. The foregoing solvent can be used in the present invention as long as it is any conventionally dispersible pigment particles. Here, an example may include propylene glycol methyl ether acetate (pr〇pylene Glyc〇1 M〇nomethy) [Ether
Acetate,PGMEA)、環己酮(Cyclohexanone)與 3-乙氧基丙酸 乙酯(Ethyl各Ethoxypropionate,EEP)等,但並不僅限於此。 為使顏料於溶劑中有更佳之分散效果及增強經分散之 顏料微粒於溶劑中的安定性,本發明顏料組合物中可進一 物包含一親二氧化碳界面活性劑(CCVphilic surfactants)。 做為本發明中親二氧化碳界面活性劑的例子,包括含氣的 碳氫化合物(fluorinated hydrocarbons),或稱氟化界面活性 劑(fluorosurfactant),但並不僅限於此。做為前述氟化界面 13 200808916 活性劑的例子’例如具有F(CF2CF2)nCH2CH2〇(CH2CH2〇)m 所示之化學式,其中n=l〜7,m=0-15 (例如,z〇nyl Fs〇1〇〇 與 Zonyl FSN-100),或全氟丁基石黃酸(perflu〇r〇butane sulfonate,PFBS)(例如 3MTM_N〇ve(>FC_4432 與 3M -No vec-FC-443 0)。親一氧化;δ炭界面活性劑於本發明顏 料組合物中的含量,以顏料的質量為丨時,其用量較佳為 0.5〜3 wt %,更佳為 〇·5〜2 wt %。 雖然本發明已以較佳實施例揭露如上,然其並非用以 限定本發明,任何熟習此技藝者,在不脫離本發明之精神 和範圍内,當可作些許之更動與潤飾,因此本發明之保護 範圍當視後附之申請專利範圍所界定者為準。 實施例一 於不使用超臨界二氧化碳下,於常溫常壓下將顏料顆 粒 red 177 (Ciba Special Chemicals Co·,香港)加入溶劑 PGMEA (Aldrich,USA)中藉以製備測試樣品,樣品中 redl77的濃度固定在1 wt%。接著於測試樣品中分別加入 不同百分比之分散劑(Hypermer PS3,ICI Americas Inc, USA)(以顏料重為基準)。經配置後之樣品以超音波震i 2 小時,接著以動態光散射粒徑分析儀(Dynamic Laser-Scattering Particle-Analyzer, Model: LSR, Protein Solutions Ltd” US A)量測,平均粒徑的讀值以兩種標準粒徑 樣品進行校正(Latex Microphere Suspensions 5016A,平均 粒徑 160nm,以及 Nanophere™ Size Standard 3200A,平均 14 200808916Acetate, PGMEA), cyclohexanone and ethyl 3-ethoxypropionate (Ethyl propionate, EEP), etc., but are not limited thereto. In order to provide a better dispersing effect of the pigment in the solvent and to enhance the stability of the dispersed pigment particles in a solvent, the pigment composition of the present invention may further comprise a CCVphilic surfactant. As an example of the carbon dioxide surfactant in the present invention, it includes, but is not limited to, fluorinated hydrocarbons, or fluorosurfactants. As an example of the aforementioned fluorinated interface 13 200808916 active agent, for example, has the chemical formula shown by F(CF2CF2)nCH2CH2〇(CH2CH2〇)m, where n=l~7, m=0-15 (for example, z〇nyl Fs 〇1〇〇 with Zonyl FSN-100), or perflu〇r〇butane sulfonate (PFBS) (eg 3MTM_N〇ve (> FC_4432 and 3M - No vec-FC-443 0). The content of the δ-carbon surfactant in the pigment composition of the present invention is preferably from 0.5 to 3 wt %, more preferably from 5 to 2 wt %, based on the mass of the pigment. The invention has been disclosed in the above preferred embodiments. However, it is not intended to limit the invention, and the invention may be modified and modified without departing from the spirit and scope of the invention. The scope is defined by the scope of the appended patent application. Example 1 Adding pigment particles red 177 (Ciba Special Chemicals Co., Hong Kong) to solvent PGMEA (Aldrich) under normal temperature and pressure without using supercritical carbon dioxide , USA) to prepare test samples, the concentration of redl77 in the sample is solid At 1 wt%, then a different percentage of dispersant (Hypermer PS3, ICI Americas Inc, USA) was added to the test sample (based on the weight of the pigment). The configured sample was ultrasonically shaken for 2 hours, followed by Measured by Dynamic Laser-Scattering Particle-Analyzer, Model: LSR, Protein Solutions Ltd US A), the average particle size reading was corrected for two standard particle size samples (Latex Microphere Suspensions 5016A) , average particle size 160nm, and NanophereTM Size Standard 3200A, average 14 200808916
Duke Sdemifk Cg,usa),所有實驗皆至少 ^兩-人,顏料微粒之平均粒徑的再現性約為± 5 %。經 mean size) ° e 一靜置後’每隔—段時間取制定其平均粒徑。經量 測所得之粒徑隨靜置時間的變化情形示於第二圖中。 參閱第二圖’可得知不添加分散劑的樣品(空白測試 組1’、其起始平均粒徑最小(約26Gnm),但經過三天後驟增 _ i米、及自此顯見超音波震蓋能暫時性的打破顏料顆粒 溶劑中的料體,但由於沒有分散綱穩定作用,經分 散的顏料顆粒會再聚集。而添加20 Wt %以上分散劑之樣 品、,經靜置後的顏料顆粒分散體的平均粒徑顯著的小於空 貝】》式組。由此頒見’所添加之分散劑能有效的提供立體 障礙,保持顏料顆粒的分散狀態,避免其再聚集。 實施例二 藝、貫驗之配置與步驟同實施例一,但於實施例一的測試 樣品進一步添加〇、i、3 wt %的親二氧化碳界面活性劑 (Zonyl FSO-100, du Pont de Nemours and Co” USA)。接著, 將測試樣品注入分散槽中以超臨界二氧化碳進行處理,其 處理條件為328.2 K、20·0 MPa,停滯時間為20分鐘。之 後,迅速釋壓至大氣壓,並將樣品導入接收槽中。同樣的 亦對各測試樣品進行平均粒徑的分析,所得之結果示於表 〇 從表一所得結果可以得知,在僅添加40 wt %之 15 200808916Duke Sdemifk Cg, usa), all experiments were at least two-person, and the average particle size of the pigment particles was about ± 5% reproducible. After the mean size) ° e, after resting, the average particle size is taken every other time. The measured particle size as a function of standing time is shown in the second graph. Referring to the second figure, it can be seen that the sample without adding a dispersant (blank test group 1' has a minimum initial average particle size (about 26 Gnm), but after three days, it suddenly increases _ i m, and since then, the ultrasonic wave is apparent. The shock cover can temporarily break the material in the pigment particle solvent, but since there is no dispersion stabilization effect, the dispersed pigment particles will reaggregate. Adding more than 20 Wt% of the dispersant sample, the pigment after standing The average particle size of the particle dispersion is significantly smaller than that of the formula. It is thus stated that the added dispersant can effectively provide steric hindrance, maintain the dispersion state of the pigment particles, and avoid re-aggregation. The configuration and procedure of the test are the same as those in the first embodiment, but the test sample of the first embodiment is further added with 〇, i, 3 wt% of a carbon dioxide surfactant (Zonyl FSO-100, du Pont de Nemours and Co" USA) Next, the test sample was injected into a dispersion tank and treated with supercritical carbon dioxide. The treatment conditions were 328.2 K, 20·0 MPa, and the stagnation time was 20 minutes. Thereafter, the pressure was quickly released to atmospheric pressure, and the sample was introduced. In the trough, the average particle size of each test sample is also analyzed, and the results are shown in Table 〇 From the results obtained in Table 1, it can be known that only 40 wt% is added. 15 200808916
HypermerPS3的情況下’經超臨界二氧化碳處理之分 的平均粒徑為25Gnm ’ *未經超臨界二氧化碳處理之分散 體的起始平均粒徑為298nm。由此顯見,經由超臨界流體 的幫助確實有替㈣顧齡的分散效果。另外,使用 複合分散劑(Hypermer PS3 + Z〇nyI FS0· 1 〇〇)則可進一步有 效的降低分散體的平均粒徑。其中,# Hy撕為In the case of Hypermer PS3, the average particle diameter of the fraction treated by supercritical carbon dioxide was 25 Gnm' * The initial average particle diameter of the dispersion which was not treated with supercritical carbon dioxide was 298 nm. It is thus apparent that the help of the supercritical fluid does have the effect of dispersing (iv) age. Further, by using a composite dispersant (Hypermer PS3 + Z〇nyI FS0·1 〇〇), the average particle diameter of the dispersion can be further effectively reduced. Among them, # Hy tear is
Wt /〇且Zonyl FSO-100為1 wt 〇/0時,分散體的平均粒押 可降至201nm。 二 實施例三 實驗步驟及條件同實施例二,其入料顏料混合物的組 :、red 177 . Hypermer PS3 : Zonyl FSO-loo : PGMEA = .001g.98 59g ’且高壓停滞溫度與壓力分別為 • κ與30.0 MPa ’但調整停滞時間為5〜6〇分鐘。同樣 的^對各測試樣品進行平均粒㈣分析,所得之結 四圖。 ^ 八^+ 1第四目目中顯不停滞時間5〜20分鐘可明顯改善 :月:果’而超過2〇分鐘後則無明顯影響。此一結果顯 I鐘;透進顏料顆粒之聚集體空隙的過程大約如 實施例四 鐘 200808916 進行平均粒徑的分析,所得之結果示第五圖與表二。 参閱第五圖’圖中顯示較高的停滯溫度有利於顏料顆 粒的分散。於高壓T,當溫度大於338.2K時,溫度效應便 的不顯著。另一方面,於定溫下,平均粒徑隨壓力增加而 下降,但超過10.0 MPa時,曲線趨於平緩。 另由表二所得結果顯示,348·2Κ與35 〇 Mpa的條件 下所獲致之分散體的平均粒徑可小至145nm。 實施例五 在此製備四個樣品,其分散條件如下所示: 樣品1 · red 177 : PGMEA=lg : 99g,不添加分散劑, 常溫常壓下超音波震盪2小時後靜置一天,平均粒徑 530nm 〇 樣品 2 : red 177 : Hypermer PS3 ·· Zonyl FSO_100 : PGMEA =lg: 0.4g: O.Oig: 98.59g,即 40 wt % Hypermer PS3 + 1 wt%Z〇nylFSO_l〇〇,常溫常壓下超音波震盪2小時, ^ 平均粒徑360nm。 才水口口 3 ♦組成同樣品 2 (40 wt % Hypermer PS3 + 1 wt %When Wt /〇 and Zonyl FSO-100 is 1 wt 〇/0, the average grain size of the dispersion can be reduced to 201 nm. The third embodiment of the experimental steps and conditions are the same as the second embodiment, the group of the pigment mixture: red 177. Hypermer PS3: Zonyl FSO-loo: PGMEA = .001g.98 59g 'and the high pressure stagnation temperature and pressure are respectively κ with 30.0 MPa 'but the stagnation time is 5 to 6 〇 minutes. The same ^ was used for the average particle (four) analysis of each test sample, and the resulting four graphs were obtained. ^ 八^+ 1 The fourth stop in the fourth target can be significantly improved by 5 to 20 minutes: Month: Fruit' and no significant effect after more than 2 minutes. This result shows that the process of penetrating the aggregate voids of the pigment particles is carried out in about the same manner as in Example 4, 200808916, and the results are shown in the fifth and second tables. See Figure 5, which shows that the higher stagnation temperature favors the dispersion of pigment particles. At high pressure T, when the temperature is greater than 338.2 K, the temperature effect is not significant. On the other hand, at a fixed temperature, the average particle size decreases with increasing pressure, but when it exceeds 10.0 MPa, the curve tends to be gentle. Further, the results obtained in Table 2 show that the average particle size of the dispersion obtained under the conditions of 348·2 Κ and 35 〇 Mpa can be as small as 145 nm. Example 5 Four samples were prepared here, and the dispersion conditions were as follows: Sample 1 · red 177 : PGMEA = lg : 99 g, without adding a dispersing agent, the ultrasonic wave was shaken at room temperature and pressure for 2 hours, and then allowed to stand for one day, the average particle 530nm 〇 sample 2 : red 177 : Hypermer PS3 · · Zonyl FSO_100 : PGMEA = lg: 0.4g: O.Oig: 98.59g, ie 40 wt % Hypermer PS3 + 1 wt% Z〇nylFSO_l〇〇, under normal temperature and pressure The ultrasonic wave oscillates for 2 hours, and the average particle size is 360 nm. Water port 3 ♦ Composition of the same sample 2 (40 wt % Hypermer PS3 + 1 wt %
Zonyi FSO-lOO) ’經超臨界二氧化碳分散,停滯溫度與壓 力分別為318.2K與5.0 MPa,停滯時間20分鐘,平均粒 徑 332nm 〇 本κ口口 4 ·組成同樣品 2 (40 wt % Hypermer PS3 + 1 wt % Zonyl FSO-100),經超臨界二氧化碳分散,停滯溫度與壓 力分別為348.2K與35.0]^0^,停滯時間20分鐘,平均粒 徑 145nm 〇 17 200808916 每一樣品於分析前均以PGMEA稀釋500倍,之後以 紫外光/可見光光譜儀(JASCO V-530, Japan)測定其光穿透 度,經分析所得結果示於第六圖。 參閱第六圖,由圖中可得知在620nm光源波長下樣品 1〜4的光穿透率分別為87.6%、91.3%、92.0%及95.8%。 由此顯示,粒徑較小的顏料微粒分散體確實具有較高的光 穿透率。Zonyi FSO-lOO) 'Supercritical carbon dioxide dispersion, stagnation temperature and pressure are 318.2K and 5.0 MPa, stagnation time 20 minutes, average particle size 332nm 〇本κ口4 · Composition same as sample 2 (40 wt % Hypermer PS3 + 1 wt % Zonyl FSO-100), supercritical carbon dioxide dispersion, stagnation temperature and pressure are 348.2K and 35.0]^0^, stagnation time 20 minutes, average particle size 145nm 〇17 200808916 Each sample before analysis After diluting 500 times with PGMEA, the light transmittance was measured by an ultraviolet/visible spectrometer (JASCO V-530, Japan), and the results obtained by the analysis are shown in the sixth graph. Referring to the sixth figure, it can be seen from the figure that the light transmittances of the samples 1 to 4 at the wavelength of the light source of 620 nm are 87.6%, 91.3%, 92.0% and 95.8%, respectively. This shows that the pigment particle dispersion having a smaller particle size does have a higher light transmittance.
18 200808916 表一 不同分散劑組成(Wt %)之分散試驗結果 常溫常壓以二氧化 下處理碳處理b —j^gLPS3Z〇nyl FSQ-l〇〇?i^j^r-粒徑減少 (g/g pigment) (g/g pigment) (nm) (nm) 250 265 201 210 -48 -70 -159 -153 2 1 0.4(40¾—~0~(^ ^-- 〇 (0 %) 0.03 (3 %) 335 4 0.4 (40 %) 0.01 (1 %) 360 J).4 (40 %) 0,03 (3 %) 363 匕分散程序為常溫常壓下以超音波震盪二小時 二臨碳士分散程序,停滯溫度與屋力為328.2 K與20.0 ,高壓停滯時間為2〇分鐘。 19 200808916 表二不同停滯溫度與壓力的分散試驗結果 壓力_溫度 平均粒徑 標準偏差 項次 (MPa) (K) (nm) (nm) 14 5 318.2 15 10 318.2 16 20 318.2 17 30 318.2 18 35 318.2 19 5 328.2 20 10 328.2 21 20 328.2 22 30 328.2 23 35 328.2 24 5 338.2 25 10 338.2 26 20 338.2 27 35 338.2 28 5 348.2 29 10 348.2 30 20 348.2 31 30 348.2 32 35 348.2 2555020072990135875 35322030886 8 6536444 3 2 2 2 2 3 2 2 11 11 2 11 1- 1- 2 11 I- 1i 118 200808916 Table 1 Dispersion test results of different dispersant composition (Wt%) at room temperature and pressure under carbon dioxide treatment b-j^gLPS3Z〇nyl FSQ-l〇〇?i^j^r-particle size reduction (g /g pigment) (g/g pigment) (nm) (nm) 250 265 201 210 -48 -70 -159 -153 2 1 0.4(403⁄4—~0~(^ ^-- 〇(0 %) 0.03 (3 %) 335 4 0.4 (40 %) 0.01 (1 %) 360 J).4 (40 %) 0,03 (3 %) 363 匕 Dispersion procedure for ultrasonic vibration at room temperature and pressure for two hours and two carbon dispersion Procedure, stagnation temperature and house strength are 328.2 K and 20.0, and high pressure stagnation time is 2 〇 minutes. 19 200808916 Table 2 Dispersion test results of different stagnation temperatures and pressures _ Temperature average particle size standard deviation (MPa) (K) (nm) (nm) 14 5 318.2 15 10 318.2 16 20 318.2 17 30 318.2 18 35 318.2 19 5 328.2 20 10 328.2 21 20 328.2 22 30 328.2 23 35 328.2 24 5 338.2 25 10 338.2 26 20 338.2 27 35 338.2 28 5 348.2 29 10 348.2 30 20 348.2 31 30 348.2 32 35 348.2 2555020072990135875 35322030886 8 6536444 3 2 2 2 2 3 2 2 11 11 2 11 1- 1- 2 11 I- 1i 1
50J70.2.632.241.5.7.8.5.7.83· 7-200^233113122273074 c 11 11 11 11 11 11 11 11 IX50J70.2.632.241.5.7.8.5.7.83· 7-200^233113122273074 c 11 11 11 11 11 11 11 11 IX
The charging rate of carbon dioxide was 2.0 cm3/min and the holding time was 20 min throughout all the runs.The charging rate of carbon dioxide was 2.0 cm3/min and the holding time was 20 min throughout all the runs.
20 200808916 【圖式簡單說明】 第一圖為執行本發明分散方法之裝置的一實施例示意圖; 第二圖為不同組成之分散劑(Hypermer PS3)配置後七曰 内’ red 177顏料分散體的平均粒徑之變化情形; 第二圖為常溫常壓且無二氧化碳參與下,不同百分比分散 劑(Hypermer pS3 與 z〇nyl FSO-100)於配置七曰 ^ 内’ red 177顏料分散體的平均粒徑之變化情形; 第四圖為不同高壓停滯時間下之red 177顏料分散體的平 均粒徑之變化情形; 第五圖為不同停滯溫度與壓力下之redl77顏料分散體的 一 平均粒徑之變化情形;以及 第六圖為不同製備條件下之red Π7顏料分散體樣品的光 穿透率變化。 【主要元件符號說明】 10分散槽 _ U儲存桶 Μ過濾器 Μ液體幫浦 工8加熱器 20壓力計 22溫度計 24接收槽20 200808916 [Simplified description of the drawings] The first figure is a schematic diagram of an embodiment of a device for performing the dispersion method of the present invention; the second figure is a dispersion of red 177 pigment in a seven-layer configuration of a dispersant (Hypermer PS3) of different compositions. The change of the average particle size; the second picture shows the average particle size of the red 177 pigment dispersion in different concentrations of the dispersant (Hypermer pS3 and z〇nyl FSO-100) in the configuration of normal temperature and normal pressure without carbon dioxide. The change of the diameter; the fourth picture shows the change of the average particle size of the red 177 pigment dispersion under different high pressure stagnation time; the fifth picture shows the change of the average particle size of the redl77 pigment dispersion under different stagnation temperatures and pressures. The situation; and the sixth figure is the change in light transmittance of the red Π7 pigment dispersion sample under different preparation conditions. [Main component symbol description] 10 dispersion tank _ U storage tank Μ filter Μ liquid pump 8 heater 20 pressure gauge 22 thermometer 24 receiving tank
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CN115850996B (en) * | 2022-11-25 | 2024-03-19 | 江苏先科半导体新材料有限公司 | Preparation method and application of modified organic pigment nanocrystals for photoresist |
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