Classifications

• • 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
  • C09D17/00—Pigment pastes, e.g. for mixing in paints
  • C09D17/001—Pigment pastes, e.g. for mixing in paints in aqueous medium
• • 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
  • 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
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
  • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
  • C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
  • C09K23/16—Amines or polyamines
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
  • C09K23/34—Higher-molecular-weight carboxylic acid esters
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
  • C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
• • 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.]
  • Y10T428/131—Glass, ceramic, or sintered, fused, fired, or calcined metal oxide or metal carbide containing [e.g., porcelain, brick, cement, 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
  • Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
  • Y10T428/1324—Flexible food casing [e.g., sausage type, etc.]

Definitions

• the present invention relates to aqueous pigment preparations containing novel nonionic polymers as dispersants, and to their use for coloring natural and synthetic materials.
• Dispersants are usually necessary for the dispersion of pigments in the liquid medium.
• Dispersing agents of particular commercial importance are, for example, for the dispersion of pigments in the preparation of pigment concentrates which are used for coloring dispersion and enamel paints, paints, coating materials and printing inks, and for coloring paper, cardboard and textiles.
• the prior art also describes pigment preparations which contain ordered polymer structures. Examples of these are EP 1 293 523, DE 10 2005 012 315 and EP 1 721 941.
• novolak dispersants contain radicals of alkylphenols, frequently nonylphenol, and their ethoxylates. Since Alkylphenolethoxylate or their degradation products are hardly degraded in the environment, they accumulate. This is problematic because they have a hormonal effect on aquatic organisms. Therefore, legislation has been adopted in many countries (eg 2003/53 / EC) restricting or prohibiting the use of substances containing alkylphenols or their ethoxylates in open material cycles. Previous studies have shown that it is still extremely difficult to synthesize dispersants that are equivalent in performance to nonionic novolac systems.
• new dispersants are required which are able to disperse low-viscosity organic pigments in a high concentration of more than 40%.
• the dispersions must be easy to produce, ie.
• the pigments must be readily wettable and easily incorporated into the aqueous medium.
• the dispersion must have a high and reproducible color strength and keep it stable over a period of several years. Likewise, all other coloristic parameters such. As the hue angle and purity can be reproduced and stable.
• the dispersion must have a low viscosity;
• the pigments must neither agglomerate nor flocculate, nor may they float or sediment.
• the dispersion should not foam or cause or accelerate foaming in the application medium.
• the dispersants should contribute to a broad compatibility of the dispersions in various application media.
• the dispersion must be shear stable, ie. Under shear, the color intensity or coloristic must not change and the dispersion must remain flocculation-stable under these conditions.
• the present invention relates to aqueous pigment preparations containing
• B is a C 2 to C 4 alkylene other than A, k is 0 or 1, m is a number from 0 to 500, preferably 0 to 50; n is a number from 0 to 500, preferably 0 to 50, where the sum m + n is 1 to 1000; X 3 is an aromatic or araliphatic radical having 3 to 30 C atoms, which optionally contains one or more of the heteroatoms N, O and S,
• Z 3 is H or (C r C 4) -alkyl
• Z b represents H or (C 1 -C 4 -alkyl J
• Z c is H or (C r C 4) alkyl
• R 1 is hydrogen or methyl
• Xb is an aromatic or araliphatic radical having 3 to 30 C atoms, which optionally contains one or more of the heteroatoms N, O and S,
• W 3 is oxygen or the group NH
• R 2 is hydrogen or methyl
• Y is an aliphatic hydrocarbon radical having 1 to
• Preferred pigment preparations contain from 5 to 80% by weight, for example from 10 to 70% by weight, of component (A).
• Preferred pigment preparations contain from 0.1 to 30% by weight, for example from 2 to 15% by weight, of component (B).
• Particularly preferred pigment preparations comprise component
• (G) 1 to 90 wt .-% water, for example 10 to 70 wt .-%, each based on the total weight (100 wt .-%) of the pigment preparation.
• the minimum concentration is independently of each other suitably at least 0.01 wt .-%, preferably at least 0.1 wt .-% , based on the total weight of the pigment preparation.
• the component (A) of the pigment preparation according to the invention is a finely divided organic or inorganic pigment or a mixture of various organic and / or inorganic pigments.
• the component (A) may also be a dye which is soluble in certain solvents and has pigment character in other solvents.
• the pigments can be used both in the form of dry powder and as water-moist press cake.
• Monoazo, disazo, laked azo, ⁇ -naphthol, naphthol AS, benzimidazolone, disazo condensation, azo metal complex pigments and polycyclic pigments, such as, for example, phthalocyanine, quinacridone, perylene, perinone, are used as organic pigments.
• those which are as finely divided as possible for the preparation of the preparations are particularly suitable, with preferably 95% and particularly preferably 99% of the pigment particles having a particle size ⁇ 500 nm.
• organic pigments are carbon black pigments, such as. B. gas or Furnaceruße; Monoazo and disazo pigments, in particular the Color Index Pigments Pigment Yellow 1, Pigment Yellow 3, Pigment Yellow 12, Pigment Yellow 13, Pigment Yellow 14, Pigment Yellow 16, Pigment Yellow 17, Pigment Yellow 73, Pigment Yellow 74, Pigment Yellow 81, Pigment Yellow® 83, Pigment Yellow® 87, Pigment Yellow® 97, Pigment Yellow® 111, Pigment Yellow® 126, Pigment Yellow® 127, Pigment Yellow® 128, Pigment Yellow® 155, Pigment Yellow® 174, Pigment Yellow® 176, Pigment Yellow® 191, Pigment Yellow® 213, Pigment Yellow 214, Pigment Red 219, Pigment Red 38, Pigment Red 144, Pigment Red 214, Pigment Red 242, Pigment Red 262, Pigment Red 266, Pigment Red 269, Pigment Red 274, Pigment Orange 13, Pigment Orange 34 or Pigment Brown 41; ⁇ -naphthol and naphthol
• Triarylcarboniumpigmente in particular the Color Index pigments Pigment Red 169, Pigment Blue 56 or Pigment Blue 61
• Diketopyrrolopyrrolpigmente in particular the Color Index pigments Pigment Red 254, Pigment Red 255, Pigment Red 264, Pigment Red 270, Pigment Red 272, Pigment Orange 71, Pigment Orange 73, Pigment Orange 81, call.
• laked dyes such as Ca, Mg, Al lacquers of dyes containing sulfonic acid and / or carboxylic acid groups.
• suitable inorganic pigments are titanium dioxides, zinc sulfides, zinc oxides, iron oxides, magnetites, manganese iron oxides, chromium oxides, ultramarine, nickel or chromium antimony titanium oxides, manganese titanium rutiles, cobalt oxides, mixed oxides of cobalt and aluminum, rutile mixed phase pigments, rare earth sulfides, spinels of cobalt with nickel and zinc , Spinels based on iron and chromium with copper zinc as well as manganese, bismuth vanadate and extender pigments.
• Color Index Pigments Pigment Yellow 184, Pigment Yellow 53, Pigment Yellow 42, Pigment Yellow Brown 24, Pigment Red 28, Pigment Blue 28, Pigment Blue 36, Pigment Green 50, Pigment Green 17, Pigment Black 11, Pigment Black 33 and Pigment White 6 are used.
• pigment dispersions can also be prepared dispersions containing as solids, for example, natural finely divided ores, minerals, difficult or insoluble salts, wax or plastic particles, dyes, crop protection and pesticides, UV absorbers, optical brighteners and polymerization stabilizers.
• the copolymers (component B) have a molecular weight of from 10 3 g / mol to 10 9 g / mol, more preferably from 10 3 to 10 7 g / mol, particularly preferably from 10 3 to 10 5 g / mol.
• These polymers can be prepared by radical polymerization of monomers corresponding to the radicals in formula (I), (II), (III) or (IV) described in brackets [] c , [] b and [] a .
• the conditions for carrying out the free-radical polymerization are known to the person skilled in the art.
• Preferred monomers of the group [] a are those in which A is ethylene and B
• Propylene, or A is propylene and B is ethylene.
• alkylene oxide units (AO) m and (BO) n can be either random or, as in the case of a preferred embodiment, arranged in a block.
• the monomers of group [] b include, for example, the following esters and amides of acrylic acid and methacrylic acid: phenyl, benzyl, toIyI, 2-phenoxyethyl, phenethyl.
• Further monomers of group [] b are vinylaromatic monomers such as styrene and its derivatives such as vinyltoluene, ⁇ -methylstyrene.
• the aromatic moiety can also be heteroaromatics, such as.
• Particularly preferred monomers of group [] b may be: styrene, 1-vinylimidazole, benzyl methacrylate, 2-phenoxyethyl methacrylate and phenethyl methacrylate.
• the monomers of group [] c include, for example, the following esters and amides of acrylic acid and methacrylic acid: methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, hexyl , 2-ethylhexyl, 3,3-dimethylbutyl, heptyl, octyl, isooctyl, nonyl, lauryl, cetyl, stearyl, behenyl, cyclohexyl, trimethylcyclohexyl, t-butylcyclohexyl, bornyl , Isobornyl, adamantyl, (2,2-dimethyl-1-methyl) propyl, cyclopentyl, 4-ethylcyclohexyl, 2-ethoxyethyl, tetrahydrofurfuryl and tetrahydro
• the monomers of group [] c include the vinyl esters of carboxylic acids, such as vinyl laurate, vinyl myristate, vinyl stearate, behenic, pivalic, neohexanoic, neoheptanoic, neooctanoic, neononanoic and
• Neodecanoate In this case, the vinyl esters can also be used from mixtures of such carboxylic acids.
• Preferred monomers of group [] c are the following alkyl esters or alkyl amides of acrylic acid and methacrylic acid: methyl, ethyl, propyl, butyl, isobutyl, 2-ethoxyethyl, myristyl, octadecyl, in particular preferably 2-ethylhexyl and lauryl.
• component (C) usually cationic, anionic, amphoteric or non-ionic compounds are used which promote the pigment wetting (wetting agents, wetting agents), for example alkyl sulfates such. Lauryl sulfate,
• Component (D) of the pigment preparations of the invention are customary dispersants suitable for the preparation of aqueous pigment dispersions and surfactants or mixtures of such substances. Usually, anionic, cationic, amphoteric or nonionic surface-active compounds are used, as described in DE-A-10 2007 021 870.
• Component (E) corresponds to organic solvents or water-soluble hydrotropic substances.
• Hydrotropes which optionally also serve as solvents, or are oligomeric or polymeric in nature, are, for example, formamide, urea, tetramethylurea, ⁇ -caprolactam, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, ⁇ -methyl- ⁇ -hydroxy-polyethylene glycol ethers, dimethyl polyethylene glycol ethers , Dipropylene glycol, polypropylene glycol, dimethylpolypropylene glycol ethers, copolymers of ethylene glycol and propylene glycol, butyl glycol, methyl cellulose, glycerol, diglycerol, polyglycerol, N-methylpyrrolidone, 1,3-diethyl-2-imidazolidinone, thiodiglycol, sodium benzenesulfonate, sodium xylenesulfonate, sodium Toluenesulfonate, sodium
• thickeners for example, thickeners, preservatives, viscosity stabilizers, grinding aids and fillers are used as component (F).
• Other common additives may include anti-settling agents, sunscreens, antioxidants,
• Degasser / defoamer, foam-reducing agents, anti-caking agents and additives that favorably influence viscosity and rheology.
• a viscosity modifier for example, polyvinyl alcohol and cellulose derivatives are suitable.
• Water-soluble natural or synthetic resins and polymers as film formers or binders for increasing adhesion and abrasion resistance are also possible.
• pH regulators organic or inorganic bases and acids are used.
• Preferred organic bases are amines, such as ethanolamine, diethanolamine, triethanolamine, N, N-dimethylethanolamine, diisopropylamine, aminomethylpropanol or dimethylaminomethylpropanol.
• Component (F) may also correspond to fats and oils of vegetable and animal origin, for example beef tallow, palm kernel fat, coconut fat, rapeseed oil, sunflower oil, linseed oil, palm oil, soybean oil, peanut oil and whale oil, Cottonseed oil, corn oil, poppy oil, olive oil, castor oil, rapeseed oil, safflower oil, soybean oil, thistle oil, sunflower oil, herring oil, sardine oil.
• the saturated and unsaturated higher fatty acids are common additives, eg.
• cyprylic capric, myristic, lauric, stearic, oleic, linoleic, linolenic, caproic, caprylic, arachidic, behenic, palmitoleic, gadoleic, erucic and ricinoleic acids, and their salts.
• Water used to prepare the pigment preparations, component (G), is preferably used in the form of desalted or distilled water. Also drinking water (tap water) and / or water of natural origin can be used.
• the present invention also provides a process for preparing the pigment preparations of the invention, which comprises reacting component (A) in the form of powder, granules or aqueous presscake in the presence of water (G) and components (B) and optionally (C ) and (D) are dispersed, then optionally water (G), and optionally one or more of the components (E) and (F) is admixed and, if appropriate, the aqueous pigment dispersion obtained is diluted with water (G).
• the components (B) and optionally one or more of the components (C), (D), (E) and (F) are first mixed and homogenized, then the component (A) is stirred into the initially introduced mixture, the component ( A) is pasted and predispersed. Depending on the grain hardness of the component (A) is then optionally finely dispersed or finely divided with cooling with the aid of a grinding or dispersing.
• agitators dissolvers (sawtooth), rotor-stator mills, ball mills, stirred ball mills such as sand and bead mills, high-speed mixers, kneaders, roller mills or high performance bead mills can be used.
• the fine dispersion or grinding of component (A) takes place up to the desired particle size distribution and can be carried out at temperatures in the range of 0 to 100 0 C, advantageously at a temperature between 10 and 70 0 C, preferably at 20 to 60 0 C.
• the pigment preparation can be further diluted with water (G), preferably deionized or distilled water.
• the pigment preparations according to the invention are suitable for pigmenting and dyeing natural and synthetic materials of all kinds, in particular aqueous paints, dispersion and enamel paints (dispersion paints). Furthermore, the pigment preparations according to the invention are suitable for coloring macromolecular materials of all kinds, for. B. of natural and synthetic fiber materials, preferably cellulose fibers, also for paper pulp dyeing as for laminates coloring. Other applications include the production of
• Printing inks in this case, for example, textile printing, flexoprinting, decorative printing or gravure printing inks, wallpaper paints, waterborne paints, wood protection systems, viscose spin dyes, paints, also powder coatings, sausage casings, seeds, fertilizers, glass, in particular glass bottles, and for the color coloring of roof tiles, for coloring for plasters, concrete, wood stains, colored pencil leads, felt-tip pens, waxes, paraffins, brushes, pastes for ballpoint pens, chalks, detergents and cleaners, shoe care products, latex products, abrasives and for coloring plastics or high-molecular materials of all kinds.
• cellulose ethers and esters such as ethyl cellulose, nitrocellulose, cellulose acetate or cellulose butyrate, natural resins or synthetic resins such as polymerization resins or condensation resins, e.g. As aminoplasts, in particular urea and melamine-formaldehyde resins, alkyd resins, acrylic resins, phenolic resins, polycarbonates, polyolefins such as polystyrene, polyvinyl chloride, polyethylene, polypropylene, polyacrylonitrile, polyacrylic acid esters, polyamides, polyurethanes or polyesters, rubber, casein, latices, silicone, silicone resins, individually or in mixture.
• aminoplasts in particular urea and melamine-formaldehyde resins
• alkyd resins acrylic resins
• acrylic resins phenolic resins
• polycarbonates polyolefins
• polystyrene polyvinyl chloride
• polyethylene polypropy
• the pigment preparations according to the invention are suitable for the production of printing inks for use in all conventional ink-jet printers, in particular for those based on the bubble jet or piezo process. These printing inks can be used to print on paper, as well as natural or synthetic fiber materials, films and plastics.
• the pigment preparations according to the invention can be used for printing various types be used by coated or uncoated substrate materials, such. As for printing on cardboard, cardboard, wood and wood-based materials, metallic materials, semiconductor materials, ceramic materials, glasses, glass and ceramic fibers, inorganic materials, concrete, leather, food, cosmetics, skin and hair.
• the substrate material may be two-dimensional flat or spatially extended, ie be designed in three dimensions and both completely or only partially printed or coated.
• the pigment preparations according to the invention are also suitable as colorants in electrophotographic toners and developers, such as.
• electrophotographic toners and developers such as.
• one- or two-component powder toners also called one- or two-component developer
• magnetic toner liquid toner
• latextoner polymerization toner
• special toners such as one- or two-component powder toners, magnetic toner, liquid toner, latextoner, polymerization toner and special toners.
• the pigment preparations of the invention as colorants in inks, preferably ink-jet inks, such as.
• ink-jet inks such as.
• solvent-based aqueous or non-aqueous basis
• microemulsion inks emulsion inks
• UV-curable inks emulsion inks
• the pigment preparations according to the invention can also be used as colorants for "color filters” for “Fiat Panel Displays", for both the additives and the subtractive color generation, also for “photo-resists”, and as colorants for electronic inks ("Electronic Inks “or” e-inks ”) or electronic paper (“ electronic paper “or” e-paper ”) are used.
• Nitrogen introduction was the monomer A, monomer C and optionally the molecular weight regulator and component 1 (ascorbic acid) of
• Redox initiator system presented in solvent under nitrogen inlet. Then, the temperature was brought under stirring to 80 0 C and within three hours, a solution of component 2 (t-BuOOH) of the redox initiator added. At the same time, dosing of monomer B started, which was completed after 3 hours. Subsequently, stirring was continued for 2 hours at this temperature, then the solvent was removed in vacuo.
• component 2 t-BuOOH
• the pigment either as a powder, granules or as a press cake, was made into a paste together with the dispersants and the other additives in deionized water and then with a dissolver (eg from VMA-Getzmann GmbH, type AE3-M1) or a homogenized and predispersed to other suitable apparatus.
• a dissolver eg from VMA-Getzmann GmbH, type AE3-M1
• the dispersion was then deionized with water to the desired
• White dispersion B for external coatings, water-based, 13.4% TiO 2
• White dispersion C for exterior coatings, water-based, binder
• White dispersion D for interior coatings, water-based, polymer dispersion, free of solvents and plasticisers, low-emission, TiO 2 , calcium carbonate
• White dispersion E for interior coatings, water-based, polyacrylates, TiO 2 , calcium carbonate
• the viscosity was measured using a cone-plate viscometer (Roto Visco 1) Haake at 20 0 C (titanium cone: 0 60 mm, 1 °), the
• the viscosity was measured immediately after preparation of the preparation, and after storage at 50 ° C. for four weeks.
• the shear stability and the foaming behavior were observed after shearing a preparation diluted to 2% with a commercially available kitchen mixer (Braun MX 32) while setting a high rotational speed.
• the more stable the preparation the lower the color-strength drop after shear in comparison to the color intensity of a sheared to an unsharpened dispersion. After stopping the mixer, the foaming behavior was observed.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Wood Science & Technology (AREA)
• Life Sciences & Earth Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Health & Medical Sciences (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Inks, Pencil-Leads, Or Crayons (AREA)
• Compositions Of Macromolecular Compounds (AREA)
• Pigments, Carbon Blacks, Or Wood Stains (AREA)
• Paints Or Removers (AREA)

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• 2007
  • 2007-08-23 DE DE102007039781A patent/DE102007039781A1/de not_active Withdrawn
• 2008
  • 2008-07-23 CN CN2008800190757A patent/CN101679794B/zh not_active Expired - Fee Related
  • 2008-07-23 KR KR1020107003836A patent/KR101477322B1/ko not_active Expired - Fee Related
  • 2008-07-23 DK DK08784980.8T patent/DK2183328T3/en active
  • 2008-07-23 ES ES08784980.8T patent/ES2529791T3/es active Active
  • 2008-07-23 WO PCT/EP2008/006021 patent/WO2009024233A1/de not_active Ceased
  • 2008-07-23 EP EP08784980.8A patent/EP2183328B1/de not_active Not-in-force
  • 2008-07-23 JP JP2010521329A patent/JP5489998B2/ja not_active Expired - Fee Related
  • 2008-07-23 US US12/674,126 patent/US8221538B2/en not_active Expired - Fee Related
  • 2008-07-23 PL PL08784980T patent/PL2183328T3/pl unknown

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