JP5525440B2 - 顔料水性分散物 - Google Patents
顔料水性分散物 Download PDFInfo
- Publication number
- JP5525440B2 JP5525440B2 JP2010506837A JP2010506837A JP5525440B2 JP 5525440 B2 JP5525440 B2 JP 5525440B2 JP 2010506837 A JP2010506837 A JP 2010506837A JP 2010506837 A JP2010506837 A JP 2010506837A JP 5525440 B2 JP5525440 B2 JP 5525440B2
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- pigment
- weight
- component
- water
- coloring
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- 239000006185 dispersion Substances 0.000 title claims description 44
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- 239000002270 dispersing agent Substances 0.000 claims description 31
- -1 azo metal complex Chemical class 0.000 claims description 27
- 238000004040 coloring Methods 0.000 claims description 19
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000000080 wetting agent Substances 0.000 claims description 8
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
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- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 claims description 3
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 3
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- 239000003960 organic solvent Substances 0.000 claims description 3
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 claims description 3
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- 229920001131 Pulp (paper) Polymers 0.000 claims description 2
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- PGEHNUUBUQTUJB-UHFFFAOYSA-N anthanthrone Chemical compound C1=CC=C2C(=O)C3=CC=C4C=CC=C5C(=O)C6=CC=C1C2=C6C3=C54 PGEHNUUBUQTUJB-UHFFFAOYSA-N 0.000 claims description 2
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 claims description 2
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 claims description 2
- 235000013580 sausages Nutrition 0.000 claims description 2
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 claims description 2
- 239000012459 cleaning agent Substances 0.000 claims 1
- 239000011505 plaster Substances 0.000 claims 1
- 239000003171 wood protecting agent Substances 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 38
- 230000015572 biosynthetic process Effects 0.000 description 34
- 238000003786 synthesis reaction Methods 0.000 description 34
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- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 16
- 238000003860 storage Methods 0.000 description 16
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- 150000001875 compounds Chemical class 0.000 description 7
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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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
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- C09D11/00—Inks
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- C—CHEMISTRY; METALLURGY
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- C—CHEMISTRY; METALLURGY
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- C09D11/00—Inks
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- C09D11/17—Writing inks characterised by colouring agents
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D11/00—Inks
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- C09D11/18—Writing inks specially adapted for ball-point writing instruments
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D15/00—Woodstains
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- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/001—Pigment pastes, e.g. for mixing in paints in aqueous medium
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- C09D7/45—Anti-settling agents
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- D—TEXTILES; PAPER
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- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
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- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
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- D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
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- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
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- D06P1/5242—Polymers of unsaturated N-containing compounds
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- D06P1/5257—(Meth)acrylic acid
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/60—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
- D06P1/613—Polyethers without nitrogen
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/60—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
- D06P1/613—Polyethers without nitrogen
- D06P1/6136—Condensation products of esters, acids, oils, oxyacids with oxiranes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/30—Ink jet printing
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H19/00—Coated paper; Coating material
- D21H19/36—Coatings with pigments
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/28—Colorants ; Pigments or opacifying agents
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1324—Flexible food casing [e.g., sausage type, etc.]
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24355—Continuous and nonuniform or irregular surface on layer or component [e.g., roofing, etc.]
Landscapes
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- General Chemical & Material Sciences (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Paints Or Removers (AREA)
- Ink Jet (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
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- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Description
従って有機顔料を40%以上の高濃度で低粘度に分散されることができる新規の分散剤が要求されている。分散物は容易に製造できなければならない。すなわち、顔料を容易に湿潤することができそして水性媒体中に容易に混入できなければならない。分散物は数年の期間にわたって安定のままである高濃度で再現性のある色濃度を有していなければならない。同様に他のあらゆる色関連パラメータ、例えば色相角及び色度に再現性がありそして安定しているべきである。分散物は泡立たず或いは使用媒体中で泡を発生させず又は泡立ち速度を早めるべきでない。更に分散剤は種々の使用媒体中の分散物に広く相容性があるべきである。さらに、分散物は剪断安定性がなければならない。すなわち、剪断の下で色濃度又は色調が著しく変化してはならない。
【課題を解決するための手段】
(A)少なくとも1種類の有機顔料及び/又は無機顔料、
(B)下記式(I)又は(II)で表される分散剤又は式(I)及び(II)で表される分散剤の混合物
aは0.01〜0.8で、
bは0.001〜0.8で、そして
cは0.001〜0.8であり、
a+b+cの合計は1であり、そして特に好ましくは
aは0.1〜0.7で、
bは0.1〜0.6で、そして
cは0.1〜0.6であり、
a+b+cの合計は1であり、
AはC2〜C4−アルキレン基であり、
BはAと異なるC2〜C4−アルキレン基であり、
Rは水素又はメチル基であり、
mは1〜500、特に1〜50の数であり;
nは1〜500、特に1〜50の数であり;
m+nの合計は2〜1000であり;
Xaは場合によっては1つ又は複数のヘテロ原子のN、O及びSを含有する炭素原子数3〜30の芳香族又は芳香脂肪族残基であり、
ZaはH又はC1〜C4−アルキル基であり、
ZbはH又はC1〜C4−アルキル基であり、
ZcはH又はC1〜C4−アルキル基であり、
R1は水素又はメチル基であり、
Xbは場合によっては1つ又は複数のヘテロ原子のN、O及びSを含有する炭素原子数3〜30の芳香族又は芳香脂肪族残基であり、
Waは酸素原子又はNH基であり、
R2は水素又はメチル基であり、
Yは直鎖状の又は分岐しているか又は環状でもよく、ヘテロ原子のN、O及び/又はSを含有していてもよく、かつ、不飽和でもよい炭素原子数1〜30、殊に6〜30、特に9〜20の脂肪族炭化水素残基であり、
Wbは酸素原子又はNH基である。]
(C)場合によっては湿潤剤、
(D)場合によっては他の界面活性剤及び/又は分散剤、
(E)場合によっては1種類又は複数種の有機溶剤及び/又は1種類又は複数種のヒドロトロピック物質、
(F)場合によっては、顔料水性分散物を製造するための別の種類の通常の添加物及び
(G)水
を含有する顔料水性調製物に関する。
(A)5〜80重量%、例えば10〜70重量%
(B)0.1〜30重量%、例えば2〜15重量%
(C)0〜10重量%、例えば0.1〜5重量%
(D)0〜20重量%、例えば1〜10重量%
(E)0〜30重量%、例えば5〜20重量%
(F)0〜20重量%、例えば0.1〜5重量%
(G)残量の水
含有する。
ピグメントブルー15:2、ピグメントブルー15:3、ピグメントブルー15:4、ピグメントブルー15:6、ピグメントブルー16、ピグメントグリーン7又はピグメントグリーン36;アンタントロン顔料、アントラキノン顔料、キナクリドン顔料、ジオキサジン顔料、インダトロン顔料、ペリレン顔料、ペリノン顔料及びチオインジゴ顔料、特にカラーインデックス顔料ではピグメントイエロー196、ピグメントレッド122、ピグメントレッド149、ピグメントレッド168、ピグメントレッド177、ピグメントレッド179、ピグメントレッド181、ピグメントレッド207、ピグメントレッド209、ピグメントレッド263、ピグメントブルー60、ピグメントバイオレット19、ピグメントバイオレット23又はピグメントオレンジ43;トリアリールカルボニウム顔料、特にカラーインデックス顔料ではピグメントレッド169、ピグメントブルー56又はピグメントブルー61;ジケトピロロピロール顔料、特にカラーインデックス顔料ではピグメントレッド254、ピグメントレッド255、ピグメントレッド264、ピグメントレッド270、ピグメントレッド272、ピグメントオレンジ71、ピグメントオレンジ73、ピグメントオレンジ81が挙げられる。
分散剤(B)の製造:
合成例1:
攪拌機、還流冷却機、内部温度計及び窒素導入管を備えたフラスコ中で、258gのポリアルキレングリコールモノメタクリレート(分子量:750、EO/PO−モル比6.3)、136.4gの2−エチルヘキシルメタクリレート、71.6gのスチレン及び16.5gの1−ドデカンチオールを660mLの第三ブタノール中に窒素導入下に最初に装入する。 次いで攪拌下に80℃の温度に加熱する。この反応温度に達した後に16.5gの開始剤AMBNを、130mLのイソブタノールに溶解した状態で1時間の間に配量供給する。次いで更に5時間、この温度で攪拌する。室温に冷却した後に溶剤を減圧下に除去する。
合成例2:
210gのポリアルキレングリコールモノメタクリレート(分子量:350、EO/PO−モル比1.7)、79.2gの2−エチルヘキシルメタクリレート、41.6gのスチレン。
258gのポリアルキレングリコールモノメタクリレート(分子量:750、EO/PO−モル比6.3)、87.5gのラウリルメタクリレート、35.8gのスチレン。
210gのポリアルキレングリコールモノメタクリレート(分子量:350、EO/PO−モル比1.7)、101.6gのラウリルメタクリレート、41.6gのスチレン。
363gのポリアルキレングリコールモノメタクリレート(分子量:1,100、EO/PO−モル比10.2、第三ブタノール中70%濃度)、117.3gのラウリルメタクリレート、48.0gのスチレン。
452gのポリアルキレングリコールモノメタクリレート(分子量:2,000、EO/PO−モル比20.5、第三ブタノール中70%濃度)、80.4gのラウリルメタクリレート、32.9gのスチレン。
210gのポリアルキレングリコールモノメタクリレート(分子量:350、EO/PO−モル比1.7)、202.8gのステアリルメタクリレート、62.4gのスチレン。
258gのポリアルキレングリコールモノメタクリレート(分子量:750、EO/PO−モル比6.3)、38.2gのイソボルニルメタクリレート、30.3gのベンジルメタクリレート。
363gのポリアルキレングリコールモノメタクリレート(分子量:1,100、EO/PO−モル比10.2、第三ブタノール中70%濃度)、39.3gのテトラヒドロフルフリルメタクリレート、87.8gのフェニルエチルメタクリレート。
452gのポリアルキレングリコールモノメタクリレート(分子量:2,000、EO/PO−モル比20.5、第三ブタノール中70%濃度)、25.0gの2−エトキシエチルメタクリレート、29.7gの1−ビニルイミダゾール。
210gのポリアルキレングリコールモノメタクリレート(分子量:350、EO/PO−モル比1.7)、69.0gのラウリルアクリレート、52.8gのベンジルメタクリレート。
258gのポリアルキレングリコールモノメタクリレート(分子量:750、EO/PO−モル比6.3)、38.2gの1−ビニル−2−ピロリドン、107.3gのスチレン。
452gのポリアルキレングリコールモノメタクリレート(分子量:2,000、EO/PO−モル比20.5、第三ブタノール中70%濃度)、31.3gの2−エトキシエチルメタクリレート、27.8gのベンジルメタクリレート。
363gのポリアルキレングリコールモノメタクリレート(分子量:1,100、EO/PO−モル比10.2、第三ブタノール中70%濃度)、58.7gのラウリルメタクリレート、43.9gのフェニルエチルメタクリレート。
258gのポリアルキレングリコールモノメタクリレート(分子量:750、EO/PO−モル比6.3)、116.3gのステアリルメタクリレート、70.9gの2−フェノキシエチルメタクリレート。
210gのポリアルキレングリコールモノメタクリレート(分子量:350、EO/PO−モル比0.43)、72.0gのラウリルアクリレート、52.8gのベンジルメタクリレート。
258gのポリアルキレングリコールモノメタクリレート(分子量:750、EO/PO−モル比0.22)、87.5gのラウリルアクリレート、35.8gのスチレン。
363gのポリアルキレングリコールモノメタクリレート(分子量:1,100、EO/PO−モル比0.30、第三ブタノール中70%濃度)、58.7gのラウリルメタクリレート、43.9gのフェニルエチルメタクリレート。
388gのポリアルキレングリコールモノメタクリレート(分子量:750、EO/PO−モル比6.3)、68.2gの2−エチルヘキシルメタクリレート、35.8gのスチレン。
517gのポリアルキレングリコールモノメタクリレート(分子量:750、EO/PO−モル比6.3)、68.2gの2−エチルヘキシルメタクリレート、35.8gのスチレン。
280gのポリアルキレングリコールモノメタクリレート(分子量:350、EO/PO−モル比1.7)、79.2gの2−エチルヘキシルメタクリレート、41.6gのスチレン。
387gのポリアルキレングリコールモノメタクリレート(分子量:750、EO/PO−モル比6.3)、87.5gのラウリルメタクリレート、35.8gのスチレン。
267gのポリアルキレングリコールモノメタクリレート(分子量:350、EO/PO−モル比1.7)、101.6gのラウリルメタクリレート、41.6gのスチレン。
ドイツ特許出願公開第10 2005 019 384号明細書、実施例1に従うコポリマー。
顔料を、粉末、顆粒として又はプレスケーキ状物として分散剤及び他の添加物と一緒に脱イオン水中で混練し、次いでAE3-M1タイプのディソルバー(製造元:VMAGetzmann GmbH社)又は他の適当な装置を用いて均一化しそして予備分散させる。続く微細分散をビーズミル(例えばVMAGetzmann GmbH社のAE3-M1)又は他の適当な分散装置によって行う。そのときサイズd=1mmのシリクワルザイト(siliquartzite )ビーズ又はジルコニウム混合酸化物ビーズを用いて冷却下に所望の色濃度及び色調が得られるまで粉砕する。その後に分散物を脱イオン水で所望の顔料濃度に調整し、粉砕媒体を分離除去しそして顔料調製物を分離する。
色濃度及び色調の測定はDIN 55986に従って行った。“擦過試験”のために分散塗料又はワニスを顔料分散物との混合後にペイントカードに塗布する。次いでペイントカードの下部を指で擦る。擦った領域が後処理されていない隣接の領域よりも高濃度であるか又は輝いている場合には不適合である(“擦過試験”はドイツ特許出願公開第2,638,946号明細書に説明されている。)。色濃度及び着色するべき媒体との適合性を6つの異なる白色分散物を用いて測定した:
1.白色分散物A(屋外用塗料、水性ベース、20%TiO2濃度)
2.白色分散物B(屋外用塗料、水性ベース、13.4%TiO2濃度)
3.白色分散物C(屋外用塗料、水性ベース、22.6%TiO2濃度)
4.白色分散物D(屋外用塗料、水性ベース、バインダー:ポリシロキサンエマルジョン、TiO2、タルク、炭酸カルシウム)
5.白色分散物E(屋内用塗料、水性ベース、溶剤及び可塑剤不含のポリマー分散物、低発光、TiO2、炭酸カルシウム)
6.白色分散物F(屋内用塗料、水性ベース、ポリアクリレート、TiO2、炭酸カルシウム)
粘度はHaake社の円錐平板粘度計(Roto Visco 1)を用いて20℃で測定した(チタン性円錐:(φ60mm、1°)。その際に粘度と剪断速度とが0〜200s-1の範囲内の関係において試験した。60s-1の剪断速度で粘度を測定した。
7.0部の成分(B) 合成例19に相当する分散剤
2.0部の成分(C) 湿潤剤
8.0部の成分(E) エチレングリコール
0.2部の成分(F) 保存剤
残量の成分(G) 水
この顔料調製物は常に濃い色濃度を有しそして安定している。6つの白色分散物A〜F中に、容易に分散しながら非常に良好に導入できる。いずれの場合も擦過試験で、擦り領域と未擦り領域との比較で色濃度に相違が無かった。調製物は、28日間、50℃で貯蔵した後でも未だ良好な流動性があるので、良好な流動性で貯蔵安定性があることが判った。製造後の粘度は642mPa.sである。この調製物は剪断安定性がありそして泡立たない。
8.0部の成分(B) 合成例23に相当する分散剤
1.0部の成分(C) 湿潤剤
10.0部の成分(E) ポリプロピレングリコール
0.2部の成分(F) 保存剤
残量の成分(G) 水
この顔料調製物は常に濃い色濃度を有しそして安定している。6つの白色分散物中に、容易に分散しながら非常に良好に導入できる。6つの場合に、擦過試験で、擦り領域と未擦り領域との比較で色濃度に相違が無かった。調製物は、28日間、50℃で貯蔵した後でも未だ良好な流動性があるので、良好な流動性で貯蔵安定性があることが判った。製造後の粘度は278mPa.sである。この調製物は剪断安定性がありそして泡立たない。
4.0部の成分(B) 合成例11に相当する分散剤
1.0部の成分(C) 湿潤剤
15.0部の成分(E) プロピレングリコール
0.2部の成分(F) 保存剤
残量の成分(G) 水
この顔料調製物は常に濃い色濃度を有しそして安定している。5つの白色分散物中に、容易に分散しながら非常に良好に導入できる。第6の白色分散物の場合には導入しに難かったが、均一にすることができた。擦過試験で、6つの場合に、擦り領域と未擦り領域との比較で色濃度に相違が無かった。調製物は、28日間、50℃で貯蔵した後でも未だ良好な流動性があるので、良好な流動性で貯蔵安定性があることが判った。製造後の粘度は1,765mPa.sである。この調製物は剪断安定性がありそして泡立たない。
12.0部の成分(B) 合成例18の式(II)に相当する分散剤
20.0部の成分(E) エチレングリコール
0.2部の成分(F) 保存剤
残量の成分(G) 水
この顔料調製物は常に濃い色濃度を有しそして安定している。6つの全ての白色分散物中に、容易に分散しながら非常に良好に導入できる。擦過試験で、6つの場合に、擦り領域と未擦り領域との比較で色濃度に相違が無かった。調製物は、28日間、50℃で貯蔵した後でも未だ良好な流動性があるので、良好な流動性で貯蔵安定性があることが判った。製造後の粘度は894mPa.sである。この調製物は剪断安定性がありそして泡立たない。
6.5部の成分(B) 合成例21に相当する分散剤
残量の成分(G) 水
この顔料調製物は常に濃い色濃度を有しそして安定している。6つの全ての白色分散物中に、容易に分散しながら非常に良好に導入できる。擦過試験で、6つの場合に、擦り領域と未擦り領域との比較で色濃度に相違が無かった。調製物は、28日間、50℃で貯蔵した後でも未だ良好な流動性があるので、良好な流動性で貯蔵安定性があることが判った。製造後の粘度は483mPa.sである。この調製物は剪断安定性がありそして泡立たない。
7.5部の成分(B) 合成例2に相当する分散剤
15.0部の成分(E) プロピレングリコール
0.2部の成分(F) 保存剤
残量の成分(G) 水
この顔料調製物は常に濃い色濃度を有しそして凝集安定性がある。6つの全ての白色分散物中に、容易に分散しながら非常に良好に導入できる。擦過試験で、6つの場合に、擦り領域と未擦り領域との比較で色濃度に相違が無かった。調製物は、28日間、50℃で貯蔵した後でも未だ良好な流動性があるので、良好な流動性で貯蔵安定性があることが判った。製造後の粘度は669mPa.sである。この調製物は剪断安定性がありそして泡立たない。
45.0部の成分(A) C.I.ピグメントレッド112
8.0部の成分(B) 比較合成例1に基づく分散剤
1.3部の成分(C) 湿潤剤
10.0部の成分(E)プロピレングリコール
0.2部の成分(F) 保存剤
35.5部の成分(G)水
この顔料調製物は白色分散物A、B、C、Eにおいてのみ濃い色濃度を有している。白色分散物D及びFにおいては色濃度は85或いは90%である。分散物系D及びFは顕著な擦過を示し、Bでは僅かな擦過が確認できる。この分散物は50℃で28日の貯蔵の後に固化したので、十分な貯蔵安定性がない。
40.0部の成分(A) C.I.ピグメントイエロー83
10.0部の成分(B) 表に記載するような合成例から式(I)又は(II) に相応する分散剤
1.0部の成分(C) 湿潤剤
10.0部の成分(E)プロピレングリコール
0.2部の成分(F) 保存剤
残量の成分(G) 水。
Claims (12)
- (A)少なくとも1種類の有機顔料及び/又は無機顔料、
(B)下記式(I)又は(II)で表される分散剤又は式(I)及び(II)で表される分散剤の混合物
aは0.01〜0.8で、
bは0.001〜0.8で、そして
cは0.001〜0.8であり、
a+b+cの合計は1であり、そして
AはC2〜C4−アルキレン基であり、
BはAと異なるC2〜C4−アルキレン基であり、
Rは水素又はメチル基であり、
mは1〜500の数であり;
nは1〜500の数であり;
m+nの合計は2〜1000であり;
Xaは炭素原子数3〜30の芳香族又は芳香脂肪族残基であり、これらの残基は場合によっては1つ又は複数のヘテロ原子のN、O及びSを含有し、
ZaはH又はC1〜C4−アルキル基であり、
ZbはH又はC1〜C4−アルキル基であり、
ZcはH又はC1〜C4−アルキル基であり、
R1は水素又はメチル基であり、
Xbは炭素原子数3〜30の芳香族又は芳香脂肪族残基であり、これらの残基は場合によっては1つ又は複数のヘテロ原子のN、O及びSを含有し、
Waは酸素原子又はNH基であり、
R2は水素又はメチル基であり、
Yは直鎖状の又は分岐しているか又は環状でもよく、ヘテロ原子のN、O及び/又はSを含有していてもよく、かつ、不飽和でもよい炭素原子数1〜30の脂肪族炭化水素残基であり、
Wbは酸素原子又はNH基である。]
(C)場合によっては湿潤剤、
(D)場合によっては他の界面活性剤及び/又は分散剤、
(E)場合によっては1種類又は複数種の有機溶剤及び/又は1種類又は複数種のヒドロトロピック物質、
(F)場合によっては、顔料水性分散物を製造するための別の種類の通常の添加物及び
(G)水
を含有する顔料水性調製物。 - 5〜80重量%の成分(A)を含有する、請求項1に記載の顔料調製物。
- 0.1〜30重量%の成分(B)を含有する、請求項1又は2に記載の顔料調製物。
- 成分(A)〜(G)がそれぞれ顔料調製物の総重量を基準として以下の組成であることを特徴とする、請求項1〜3のいずれか一つに記載の顔料調製物:
(A)5〜80重量%、
(B)0.1〜30重量%、
(C)0〜10重量%。
(D)0〜20重量%、
(E)0〜30重量%、
(F)0〜20重量%、
(G)残量の水 - 成分(A)〜(G)がそれぞれ顔料調製物の総重量を基準として以下の組成であることを特徴とする、請求項1〜4のいずれか一つに記載の顔料調製物:
(A)10〜70重量%、
(B)2〜15重量%、
(C)0.1〜5重量%、
(D)1〜10重量%、
(E)5〜20重量%、
(F)0.1〜5重量%、
(G)残量の水 - 成分(A)の有機顔料がモノアゾ顔料、ジアゾ顔料、レーキ化アゾ顔料、β−ナフトール顔料、ナフトールAS顔料、ベンズイミダゾロン顔料、ジスアゾ縮合顔料、アゾ金属錯塩顔料又は、フタロシアニン顔料、キナクリドン顔料、ペリレン顔料、ペリノン顔料、チオインジゴ顔料、アンタントロン顔料、アントラキノン顔料、フラバントロン顔料、インダトロン顔料、イソバイオラントロン顔料、ピラントロン顔料、ジオキサジン顔料、キノフタロン顔料、イソインドリノン顔料、イソインドリン顔料及びジケトピロロピロール顔料の群から選ばれた多環式顔料又はカーボンブラックである、請求項1〜5のいずれか一つに記載の顔料調製物。
- 成分(B)中にアルキレンオキサイド単位(A−O)m及び(B−O)nがブロック状に配置されている、請求項1〜6のいずれか一つに記載の顔料調製物。
- 成分(B)において(A−O)mがプロピレンオキサイド単位でありそして(B−O)nがエチレンオキサイド単位であるか又は(A−O)mがエチレンオキサイド単位でありそして(B−O)nがプロピレンオキサイド単位であり、エチレンオキサイド単位のモル分率がエチレンオキサイド単位とプロピレンオキサイド単位との合計を基準として50〜98%である、請求項1〜7のいずれか一つに記載の顔料調製物。
- 請求項1〜8のいずれか一つに記載の顔料調製物を製造する方法において、粉末、顆粒又は水性プレスケーキ状物の状態の成分(A)を水(G)並びに成分(B)の存在下に及び場合によっては成分(C)及び(D)も存在するもとで分散させ、次いで場合によっては水(G)並びに場合によっては成分(E)及び(F)の1種類又は複数種を混入しそして場合によっては得られる顔料水性分散物を水(G)で希釈するか又は
成分(B)を予めに装填しそして場合によっては成分(C)、(D)、(E)及び(F)の1種類又は複数種を最初に混入均一化し、次いで成分(A)を予め装填された混合物中に導入し、そのときに該成分(A)がペースト化し始めており、かつ、予め分散されていることを特徴とする、上記方法。 - 請求項1〜8のいずれか一つに記載の顔料調製物の、天然又は合成材料の着色のための使用。
- 水性塗料、分散及びワニス着色剤、水希釈性ワニス、壁紙着色剤及び印刷インクの着色のための請求項10に記載の使用。
- 天然及び合成繊維材料、セルロース繊維の着色、紙パルプの着色、積層体の着色及び印刷インク、インクジェットインク、電子写真トナー、粉末塗料、カラーフィルター、電子インク及び“電子ペーパー”、カラーフィルター、木材防腐系、ビスコース原液着色剤、ソーセージケーシング、種子製品、肥料、ガラス瓶の製造及び屋根板の着色、漆喰、コンクリート、木材着色剤、有色鉛筆心、フェルトペン、ワックス、パラフィン、グラフィックインク、ボールペン用ペースト、チョーク、洗剤及び浄化剤、靴手入れ用剤、ラテックス製品、摩耗剤の着色及びプラスチックの着色のための、請求項10に記載の使用。
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DE102007021870A DE102007021870A1 (de) | 2007-05-10 | 2007-05-10 | Wässrige Pigmentpräparationen |
PCT/EP2008/003457 WO2008138487A1 (de) | 2007-05-10 | 2008-04-29 | Wässrige pigmentpräparationen |
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EP (1) | EP2147066B1 (ja) |
JP (1) | JP5525440B2 (ja) |
CN (1) | CN101622320B (ja) |
DE (2) | DE102007021870A1 (ja) |
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DE102007021870A1 (de) | 2008-11-20 |
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US20100116010A1 (en) | 2010-05-13 |
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EP2147066A1 (de) | 2010-01-27 |
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