EP3313947A1 - Neue naphthol as-pigmente - Google Patents

Neue naphthol as-pigmente

Info

Publication number
EP3313947A1
EP3313947A1 EP16726858.0A EP16726858A EP3313947A1 EP 3313947 A1 EP3313947 A1 EP 3313947A1 EP 16726858 A EP16726858 A EP 16726858A EP 3313947 A1 EP3313947 A1 EP 3313947A1
Authority
EP
European Patent Office
Prior art keywords
pigments
alkyl
phenyl
hydrogen
methyl
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.)
Withdrawn
Application number
EP16726858.0A
Other languages
German (de)
English (en)
French (fr)
Inventor
Ulrike Rohr
Joachim Eichhorn
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Avient Switzerland GmbH
Original Assignee
Clariant Plastics and Coatings Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Clariant Plastics and Coatings Ltd filed Critical Clariant Plastics and Coatings Ltd
Publication of EP3313947A1 publication Critical patent/EP3313947A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0018—Monoazo dyes prepared by diazotising and coupling from diazotized aminopolycyclic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
    • C08K5/23—Azo-compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
    • 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
    • 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
    • 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
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/322—Pigment inks
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • 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
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • 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
    • G03G9/091—Azo dyes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • 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
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

Definitions

  • Novel Naphthol AS Pigments Description The present invention is in the field of azo pigments.
  • Naphthol AS pigments are of particular technical interest, since these usually achieve high color strengths and the magenta range of
  • the present invention now provides novel naphthol AS pigments
  • the invention relates to naphthol AS pigments of the general formula (I)
  • R 2 is hydrogen or C 1 -C 4 -alkyl
  • Y is C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy
  • Z ' is hydrogen, phenyl, naphthyl, or substituted phenyl or
  • substituted naphthyl wherein the substituents 1, 2, 3 or 4 in the number and selected from the group halogen, nitro, cyano, C1-C4-
  • naphthol AS pigments of the general formula (I) in which R 1 is methyl are also preferred.
  • naphthol AS pigments of the general formula (I) in which R 2 is hydrogen are also preferred.
  • naphthol AS pigments of the general formula (I) in which R 1 is methyl and R 2 is hydrogen.
  • Y is C 1 -C 2 -alkoxy or C 1 -C 2 -alkyl, in particular methyl or methoxy.
  • naphthol AS pigments of the general formula (I) in which Z 'is hydrogen, phenyl or substituted phenyl, where the substituents 1, 2, 3 or 4 are present in the number and selected from the group consisting of halogen, such as F, Cl or Br , Nitro, cyano, C 1 -C 4 -alkoxycarbonyl, carbamoyl, C 1 -C 4 -alkylcarbamoyl,
  • naphthol AS pigments of the general formula (I) in which Z 'is hydrogen, phenyl or phenyl substituted by nitro, cyano, C 1 -C 4 -alkyl, in particular methyl or ethyl.
  • naphthol AS pigments of the general formula (I) in which Z 'is hydrogen, phenyl or phenyl substituted by nitro, cyano, C 1 -C 4 -alkyl, in particular methyl or ethyl.
  • naphthol AS pigments of the general formula (I) in which Z 'is hydrogen, phenyl or phenyl substituted by nitro, cyano, C 1 -C 4 -alkyl, in particular methyl or ethyl.
  • R 1 is methyl
  • R 2 is hydrogen
  • Y is C 1 -C 4 -alkoxy, in particular methoxy or ethoxy
  • Z is phenyl, methylphenyl or nitrophenyl.
  • the pigments of the formula (I) according to the invention can be prepared by diazotization of an amine of the formula (III)
  • the substituents R 1 , R 2 , Y in the formula (III) and Z 'in the formula (IV) in this case have one of the meanings given above.
  • the resulting pigment suspension can be filtered and the resulting moist presscake is expediently dried to constant weight.
  • the azo coupling reaction is preferably carried out in aqueous solution or
  • Suspension and preferably at a pH between 3 and 9, but it can also be used organic solvents, optionally in admixture with water, for example alcohols having 1 to 10 carbon atoms, such as
  • Ethers such as methyl isobutyl ether, tetrahydrofuran or
  • Glycol ethers such as monomethyl or monoethyl ethers of ethylene or propylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, butyl glycols or methoxybutanol; Ketones, such as acetone,
  • aliphatic acid amides such as formamide, dimethylformamide, N-methylacetamide or ⁇ , ⁇ -dimethylacetamide; Urea derivatives, such as tetramethylurea; or cyclic carboxylic acid amides, such as N-methylpyrrolidone, valero or caprolactam; Esters, such as carboxylic acid C 1 -C 6 -alkyl esters, such as butyl formate,
  • Ethyl acetate or propionic acid propyl ester or carboxylic acid C 1 -C 6 -glycol ester; or glycol ether acetates such as 1-methoxy-2-propyl acetate; or
  • Phthalic or benzoic acid C 1 -C 6 -alkyl esters, such as ethyl benzoate; cyclic esters such as caprolactone; Nitriles, such as acetone it l or benzonitrile;
  • aliphatic or aromatic hydrocarbons such as cyclohexane or benzene; or benzene substituted by alkyl, alkoxy, nitro or halogen, such as toluene, xylenes, ethylbenzene, anisole, nitrobenzene, chlorobenzene, o-dichlorobenzene,
  • solvents mentioned can also be used as mixtures.
  • water-miscible solvents are used.
  • adjuvants such as surfactants, pigmentary and non-pigmentary dispersants, fillers, extenders, resins, waxes, defoamers, anti-dusting agents, extenders, colorants for
  • Light stabilizers or a combination thereof can be used.
  • the addition of the adjuvant can be carried out at any time before, during or after the synthesis, at once or in several portions.
  • the aids can be added, for example, directly to the solutions or suspensions of the reactants, but also during the reaction in liquid, dissolved or suspended form.
  • the total amount of auxiliaries added may be from 0 to 40% by weight, preferably from 1 to 30% by weight, particularly preferably from 2.5 to 25% by weight, based on the total weight of the pigment plus auxiliary.
  • Suitable surfactants are anionic or anionic, cationic or cationic and nonionic substances or mixtures of these agents. Examples of surfactants, pigmentary and non-pigmentary dispersants which can be used in the process according to the invention are described in US Pat
  • buffer solutions may also be added, preferably organic acids and their salts, such as
  • Citric acid / citrate buffer or of inorganic acids and their salts, such as phosphoric acid / phosphate buffer or
  • Carbonic acid / bicarbonate or carbonate buffer Carbonic acid / bicarbonate or carbonate buffer.
  • azo coupling can be by direct stirring of the aqueous reaction mixture at temperatures between 20 to 95 ° C a finish
  • a finish includes picking up the prepared naphthol AS pigment, either directly from the synthesis or after intermediate isolation, e.g. when
  • Preferred solvents are C 3 -C 4 -alcohols, glycol ethers and chlorinated benzenes, for example isopropanol, isobutanol, butoxyethanol, ortho-dichlorobenzene or a mixture thereof.
  • the amount of the solvent is preferably 1 to 30% by volume
  • the pigment finish is preferably at a temperature between 20 and 150 ° C, in particular between 40 and 90 ° C, optionally under pressure, and preferably for 0.1 to 2 hours, in particular 0.25 to 1 hours, and preferably at
  • the naphthol AS pigments according to the invention are distinguished by a magenta color and / or high brilliance (chroma), which makes the pigments according to the invention attractive for many industrial applications.
  • chroma high brilliance
  • Use materials of natural or synthetic origin such as plastics, resins, paints, paints and seeds.
  • the naphthol AS pigments of the invention are usually used in an amount of 0.05 to 30% by weight, preferably 0.1 to 15% by weight.
  • the pigments according to the invention are furthermore suitable as colorants in electrophotographic toners and developers, for example one- or two-component powder toners (also called one- or two-component developers), magnetic toners, liquid toners, latex toners, polymerization toners and special toners. They can be used in conventional toner production processes by extrusion but also in chemical toner production processes such as emulsion, aggregation or suspension polymerization.
  • Toner particles may also be used for cosmetic and pharmaceutical applications, e.g. B. for coating tablets.
  • Typical toner binders are polymerization, polyaddition and
  • Polycondensation resins such as styrene, styrene acrylate, styrene butadiene, acrylate, polyester, phenolic epoxy resins, polysulfones, polyurethanes, individually or in Combination, as well as polyethylene and polypropylene, which may contain other ingredients such as charge control agents, waxes or flow aids, or be modified afterwards with these additives.
  • the pigments according to the invention are suitable as colorants in aqueous and non-aqueous-based ink-jet inks, microemulsion inks, UV inks and also in inks which operate according to the hot-melt method.
  • Ink-jet inks generally contain a total of 0.5 to 50 wt .-%,
  • Water-based ink jet inks contain substantially 0.5 to 30 wt .-%, preferably 1 to 15 wt .-% of the inventive pigments, 70 bis
  • Solvent based ink jet inks contain substantially 0.5 to
  • solvent-based ink-jet inks may contain carrier materials and binders that are soluble in the "solvent," such as polyolefins, natural and non-aqueous
  • Synthetic rubber polyvinyl chloride, vinyl chloride / vinyl acetate copolymers, polyvinyl butyrals, wax / latex systems or combinations thereof
  • the solvent-based ink-jet inks may contain other additives such.
  • Microemulsion inks are based on organic solvents, water and optionally an additional substance which acts as an interface mediator (Surfactant).
  • Microemulsion inks contain from 0.5 to 30% by weight, preferably from 1 to 15% by weight, of the pigments according to the invention, from 0.5 to 95% by weight of water and from 0.5 to 95% by weight of organic solvents and / or interface mediator.
  • UV inks typically consist of monomers of low molecular weight mono-, di-, tri-, tetra- and / or penta-functional acrylates and / or acrylate, urethane, epoxy, or polyester-based oligomers. The UV inks will be
  • UV-curable inks contain substantially 0.5 to 30 wt .-% of
  • pigments according to the invention 0.5 to 95 wt .-% water, 0.5 to 95 wt .-% of an organic solvent or solvent mixture, 0.5 to
  • a radiation-curable binder 50 wt .-% of a radiation-curable binder and optionally 0 to 10 wt .-% of a photoinitiator.
  • Hot-melt inks are usually based on waxes, fatty acids, fatty alcohols or sulfonamides, which are solid at room temperature and liquid when heated, with the preferred melting range between about 60 and about 140 ° C.
  • Hot-melt ink-jet inks consist essentially of 20 to 90 wt .-% wax and 1 to 10 wt .-% of the pigments of the invention. Furthermore, 0 to 20 wt .-% of an additional polymer (as a "dye remover"), 0 to
  • plasticizer 20% by weight of plasticizer, 0 to 10% by weight of tackifier additive, 0 to 10% by weight of transparent stabilizer (prevents, for example, the crystallization of the wax) and 0 to 2% by weight of antioxidant.
  • the pigments according to the invention are also suitable as colorants for color filters, both for additive and for subtractive color generation, and as colorants for electronic inks ("electronic inks” or “e-inks”) or “electronic paper” ("e-inks”). paper ").
  • pigments are in the form of a paste or pigmented Photoresists in suitable binders (acrylates, acrylic esters, polyimides,
  • TN-LCD (Super) Twisted Nematic LCD
  • the pigmented color filters may also be applied by ink-jet printing or other suitable printing techniques.
  • the pigments according to the invention can also be used for the production of classic printing inks (such as, for example, offset printing, flexographic printing, intaglio printing, etc.).
  • the pigments according to the invention are distinguished by a bluish magenta hue and / or by a high brilliance.
  • the clarified diazonium salt solution from a1) is initially charged, adjusted by the addition of about 38 g of sodium acetate (in the form of a 4N solution) to pH 4.3 to 4.5 and cooled by addition of ice to 10 ° C. Thereafter, with stirring, the warm coupler solution from a2) is metered in over the course of 1 to 1, 5 h, wherein
  • Coupling reaction is heated for 1 h above 50 ° C, then filtered and washed with water. After drying and grinding, 468 g of a dark red powder of the pigment of the formula (2) are obtained.
  • the chroma C is the
  • pigments according to the invention preferably between 58 and 74 (74> C> 58) and particularly preferably between 60 and 70 (70> C> 60).
  • hue h is preferably between 345 and 360 or
  • the paint thus obtained is transferred by means of a hand coater on a film-drawing device and in 100 ⁇ wet film thickness on a probe card (chromo cardboard, white, cast-coated on one side, 300 g / m 2 , size 100 x 230 mm) mounted.
  • the Lacquer card is first dried for 15 min at room temperature and then 60 min in a drying oven at 60 ° C.
  • the chroma (C) and hue (h) values are measured by a D65 standard light lamp at a viewing angle of 10 ° with a Datacolor Spectraflash-SF600-PLUS CT spectrophotometer according to DIN 5033-7, ISO 7724-2.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Architecture (AREA)
  • Structural Engineering (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Optical Filters (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Paints Or Removers (AREA)
EP16726858.0A 2015-06-25 2016-05-31 Neue naphthol as-pigmente Withdrawn EP3313947A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102015211827.4A DE102015211827A1 (de) 2015-06-25 2015-06-25 Neue Naphthol AS-Pigmente
PCT/EP2016/062290 WO2016206925A1 (de) 2015-06-25 2016-05-31 Neue naphthol as-pigmente

Publications (1)

Publication Number Publication Date
EP3313947A1 true EP3313947A1 (de) 2018-05-02

Family

ID=56098242

Family Applications (1)

Application Number Title Priority Date Filing Date
EP16726858.0A Withdrawn EP3313947A1 (de) 2015-06-25 2016-05-31 Neue naphthol as-pigmente

Country Status (6)

Country Link
US (1) US10752779B2 (ja)
EP (1) EP3313947A1 (ja)
JP (1) JP6854782B2 (ja)
CN (1) CN107667148B (ja)
DE (1) DE102015211827A1 (ja)
WO (1) WO2016206925A1 (ja)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7391649B2 (ja) 2019-12-12 2023-12-05 キヤノン株式会社 マゼンタトナー
JP7353954B2 (ja) 2019-12-12 2023-10-02 キヤノン株式会社 マゼンタトナー

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2006211A (en) * 1933-02-22 1935-06-25 Gen Aniline Works Inc Colored rubber products and process of producing them
US2084555A (en) * 1934-02-27 1937-06-22 Gen Aniline Works Inc Colored rubber products and a process of producing them
US3113938A (en) * 1959-12-12 1963-12-10 Hoechst Ag Water-insoluble monoazo-dyestuffs and process for their manufacture
FR1278821A (fr) * 1960-12-12 1961-12-15 Hoechst Ag Colorants monoazoïques insolubles dans l'eau et leur préparation
NL125848C (ja) 1963-03-13
US5482803A (en) * 1992-02-07 1996-01-09 Canon Kabushiki Kaisha Process for preparing filter
CN1100829C (zh) * 2000-03-28 2003-02-05 沈阳化工研究院 红色有机颜料及用途
DE10049200A1 (de) 2000-10-05 2002-04-11 Clariant Gmbh Verfahren zur Herstellung von Azofarbmitteln
JP4398139B2 (ja) * 2002-10-01 2010-01-13 大日精化工業株式会社 インクジェットインキ用アゾ顔料、ならびにインクジェットインキおよびその製造方法
DE502004002125D1 (de) * 2003-08-19 2007-01-04 Clariant Produkte Deutschland Mischkristalle mit derivaten von c.i. pigment red 170
DE102004019560A1 (de) 2004-04-22 2005-11-10 Clariant Gmbh Hochreine Naphthol AS-Pigmente
DE102004019561A1 (de) * 2004-04-22 2005-11-10 Clariant Gmbh Verfahren zur Herstellung hochreiner Azofarbmittel
CN101466697B (zh) * 2006-04-13 2013-05-15 保土谷化学工业株式会社 氧化型混合环状苯酚硫化物、使用其的电荷控制剂及调色剂
DE102006052139A1 (de) * 2006-11-06 2008-05-08 Clariant International Limited Universelle Stir-in Pigmente

Also Published As

Publication number Publication date
US20180179387A1 (en) 2018-06-28
CN107667148A (zh) 2018-02-06
US10752779B2 (en) 2020-08-25
JP2018528278A (ja) 2018-09-27
DE102015211827A1 (de) 2016-12-29
WO2016206925A1 (de) 2016-12-29
JP6854782B2 (ja) 2021-04-07
CN107667148B (zh) 2021-09-07

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