JP6978531B2 - 塩素化銅フタロシアニン顔料 - Google Patents
塩素化銅フタロシアニン顔料 Download PDFInfo
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- JP6978531B2 JP6978531B2 JP2020019411A JP2020019411A JP6978531B2 JP 6978531 B2 JP6978531 B2 JP 6978531B2 JP 2020019411 A JP2020019411 A JP 2020019411A JP 2020019411 A JP2020019411 A JP 2020019411A JP 6978531 B2 JP6978531 B2 JP 6978531B2
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- phthalocyanine
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/10—Obtaining compounds having halogen atoms directly bound to the phthalocyanine skeleton
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- 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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0034—Mixtures of two or more pigments or dyes of the same type
- C09B67/0035—Mixtures of phthalocyanines
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- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
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- 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
- C09B67/0002—Grinding; Milling with solid grinding or milling assistants
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- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
- C09B67/0016—Influencing the physical properties by treatment with a liquid, e.g. solvents of phthalocyanines
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- 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
- C09B67/0022—Wet grinding of pigments
- C09B67/0023—Wet grinding of pigments of phthalocyanines
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0025—Crystal modifications; Special X-ray patterns
- C09B67/0026—Crystal modifications; Special X-ray patterns of phthalocyanine pigments
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- 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
- C09B67/0032—Treatment of phthalocyanine pigments
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- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
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- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/322—Pigment inks
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- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/003—Pigment pastes, e.g. for mixing in paints containing an organic pigment
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- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/03—Powdery paints
- C09D5/033—Powdery paints characterised by the additives
- C09D5/035—Coloring agents, e.g. pigments
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- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/41—Organic pigments; Organic dyes
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
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- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/09—Colouring agents for toner particles
- G03G9/0906—Organic dyes
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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Description
本出願は、「Chlorinated Copper Phthalocyanine Pigments(塩素化銅フタロシアニン顔料)」と題する、2015年6月4日出願の米国仮特許出願第62/170756号の優先権を主張し、その内容全体は援用により本明細書に組み入れられる。
0.4<m+n≦4
m≧n
n>0.2、
式中mはα位における塩素置換基の平均数を表し、nはβ位における塩素置換基の平均数を表す、塩素化銅フタロシアニン顔料に関する。
式(I)
まず、顔料乾燥粉体を分散剤のNuosperse W−28で1:2の比(顔料:分散剤)で混合し、DCP解析で使用する分散体を調製した。超音波浴、超音波ホーンの順に用いて得られたペーストを脱イオン水に1:100の比で分散した。測定をBrookhavenBI−DCP粒径分析計を用いて、ディスク速度10,000RPM、室温で実施した。BrookhavenBI−DCPソフトウェアのバージョン5.87を用いてデータ加工及び粒径計算を行った。
1L樹脂フラスコに、92.8gの無水フタル酸、27.2gの3−クロロ無水フタル酸、11.0gの4−クロロ無水フタル酸、163.5gの尿素、20.7gの塩化銅(I)、0.5gの二モリブデン酸アンモニウム及び705gのジクロロトルエンを入れ、撹拌しながら200℃に加熱した。200℃で2時間撹拌して反応させた。その後、前記内容物を室温へ冷却し、前記溶媒を減圧下で除去した。粗残渣を、2500gの水及び100gの濃硫酸中90℃で2時間撹拌した。粗プレスケーキをろ過により単離し、導電率100μmhos/cm未満で洗浄して乾燥した後オスタライザーミキサーで破砕した。得られた青色粗生成物(粗生成物#1)を、X線解析で検証した(表1、図1)。その後粗生成物#1(27g)を実験用混錬機により80℃で6時間かけて塩(216g)及びプロピレングリコール(53g)で摩滅させた。摩滅完了時に、前記混合物を水に懸濁して大気温で撹拌し、得られたスラリーのpHが1.0未満(pH<1.0)になるまで濃塩化水素(HCl)を添加した。その後前記スラリーを90℃に加熱し1時間保持した後ろ過した。前記顔料をろ過により単離し、導電率が100μmhos/cm未満になるまで洗浄し、乾燥し、オスタライザーミキサーで破砕し、60メッシュスクリーンを通過させることにより最終製品(顔料#1)得た。顔料#1及び標準品(Palomar(登録商標) Blue 248−4816)を、顔料/バインダー比8.83/3.19でSkandexシェーカー上でデュポン(DuPont)水性塗料系に3時間分散させた。顔料#1を含む塗料製剤及び前記標準品を、調温調湿スプレーブース内でパネルにスプレーした。前記スプレーブース内の設備は、Automatic Test Panel Spray Machine(自動テストパネルスプレー機)(Spraymation,Inc.)と呼ばれている。
1L樹脂フラスコに、92.8gの無水フタル酸、22.6gの3−クロロ無水フタル酸、15.5gの4−クロロ無水フタル酸、163.5gの尿素、20.7gの塩化銅(I)、0.5gの二モリブデン酸アンモニウム及び705gのジクロロトルエンを入れ、撹拌しながら200℃に加熱した。200℃で2時間撹拌して反応させた。その後、前記反応混合物を室温へ冷却し、前記溶媒を減圧下で除去した。得られた残渣を、2800gの水及び100gの濃硫酸中90℃で2時間撹拌した。前記顔料をろ過により単離し、導電率が100μmhos/cm未満になるまで洗浄して乾燥した後オスタライザーミキサーで破砕した。得られた青色粗生成物(粗生成物#2)を、X線解析で検証した(表2、図2)。粗生成物#2(37.5g)を、ステンレス製ジャー内で大気温で6時間ボールミル粉砕した。前記ジャーには、〜870gの1/4インチボールと〜97gの小釘を入れておいた。その後前記ボールミル粉砕粗生成物(31g)を実験用混錬機により80℃で6時間かけて塩(248g)及びプロピレングリコール(61g)で摩擦粉砕した。摩擦粉砕完了時に、前記混合物を水に懸濁して大気温で撹拌し、得られたスラリーのpHが1.0未満(pH<1.0)になるまで濃塩化水素(HCl)を添加した。その後前記スラリーを90℃に加熱し1時間保持した後ろ過した。前記顔料をろ過により単離し、導電率が100μmhos/cm未満になるまで洗浄し、乾燥し、オスタライザーミキサーで破砕し、60メッシュスクリーンを通過させることにより最終製品(顔料#2)を得た。顔料#2及び標準品(Palomar(登録商標) Blue 248−4816)を、顔料/バインダー比8.83/3.19でSkandexシェーカー上でデュポン(DuPont)水性塗料系に3時間分散させた。顔料#2を含む塗料製剤及び前記標準品を、調温調湿スプレーブース内でパネルにスプレーした。前記スプレーブース内の設備は、Automatic Test Panel Spray Machine(自動テストパネルスプレー機)(Spraymation,Inc.)と呼ばれている。
1L樹脂フラスコに、92.8gの無水フタル酸、27.2gの3−クロロ無水フタル酸、11.0gの4−クロロ無水フタル酸、163.5gの尿素、10.4gの塩化銅(I)、16.7gの硫酸銅(II)、0.5gの二モリブデン酸アンモニウム及び485gの軽度分岐アルキルベンゼン溶媒を入れ、撹拌しながら200℃に加熱した。200℃で2.5〜3時間撹拌して反応させた。その後、前記内容物を室温へ冷却し、前記溶媒を減圧下で除去した。得られた粗残渣を、2500gの水及び100gの濃硫酸中90℃で2時間撹拌した。粗プレスケーキをろ過により単離し、導電率が100μmhos/cm未満になるまで洗浄して乾燥した後オスタライザーミキサーで破砕した。得られた青色粗生成物(粗生成物#3)を、X線解析で検証した。その後粗生成物#3(27g)を実験用混錬機により80℃で6時間かけて塩(216g)及びプロピレングリコール(52g)で摩擦粉砕した。摩擦粉砕完了時に、前記混合物を水に懸濁して大気温で撹拌し、得られたスラリーのpHが1.0未満(pH<1.0)になるまで濃塩化水素(HCl)を添加した。その後前記スラリーを90℃に加熱し1時間保持した後ろ過した。前記顔料をろ過により単離し、導電率が100μmhos/cm未満になるまで洗浄し、乾燥し、オスタライザーミキサーで破砕し、60メッシュスクリーンを通過させることにより最終製品を得た。顔料#3及び標準品(Palomar(登録商標) Blue 248−4816)を、顔料/バインダー比8.83/3.19でSkandexシェーカー上でデュポン(DuPont)水性塗料系に3時間分散させた。顔料#3を含む塗料製剤及び前記標準品を、調温調湿スプレーブース内でパネルにスプレーした。前記スプレーブース内の設備は、Automatic Test Panel Spray Machine(自動テストパネルスプレー機)(Spraymation,Inc.)と呼ばれている。
本開示には以下の実施形態も開示される。
[実施形態1]
塩素化銅フタロシアニン顔料組成物であって、50%超のβ結晶形を含み、α位及びβ位を有する下記の構造を有し、
0.4<m+n≦4
m≧n
n>0.2、
式中mは前記α位における塩素置換基の平均数を表し、nは前記β位における塩素置換基の平均数を表す、塩素化銅フタロシアニン顔料組成物。
[実施形態2]
粒径が約20〜90nmである、実施形態1に記載のフタロシアニン顔料組成物。
[実施形態3]
粒径が約30〜70nmである、実施形態1に記載のフタロシアニン顔料組成物。
[実施形態4]
95Wティントにおける色相角(H)が約225°〜242°である、実施形態1に記載のフタロシアニン顔料組成物。
[実施形態5]
前記顔料組成物が少なくとも一種の添加剤を含む、実施形態1に記載のフタロシアニン顔料組成物。
[実施形態6]
前記添加剤が顔料誘導体である、実施形態5に記載のフタロシアニン顔料組成物。
[実施形態7]
前記添加剤が修飾フタロシアニン顔料誘導体である、実施形態6に記載のフタロシアニン顔料組成物。
[実施形態8]
前記添加剤がスルホン化フタロシアニン顔料誘導体である、実施形態7に記載のフタロシアニン顔料組成物。
[実施形態9]
前記顔料組成物が自動車用塗料系に用いられる、実施形態1に記載のフタロシアニン顔料組成物。
[実施形態10]
実施形態1に記載の塩素化銅フタロシアニン顔料組成物を含む、コーティング、インク、水性又は溶媒性顔料製剤、電子写真用トナー及び現像剤、プラスチック、カラーフィルター、パウダーコーテイング材。
Claims (6)
- 粒径が20〜90nmである、請求項1に記載のフタロシアニン顔料組成物。
- 粒径が30〜70nmである、請求項1に記載のフタロシアニン顔料組成物。
- 前記顔料組成物が少なくとも一種の添加剤を含む、請求項1に記載のフタロシアニン顔料組成物。
- 前記顔料組成物が自動車用塗料系に用いられる、請求項1に記載のフタロシアニン顔料組成物。
- 請求項1に記載の塩素化銅フタロシアニン顔料組成物を含む、コーティング、インク、水性又は溶媒性顔料製剤、電子写真用トナー及び電子写真用現像剤、プラスチック、カラーフィルター、パウダーコーテイング材。
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