EP2102290A2 - Universelle stir-in pigmente - Google Patents
Universelle stir-in pigmenteInfo
- Publication number
- EP2102290A2 EP2102290A2 EP07818528A EP07818528A EP2102290A2 EP 2102290 A2 EP2102290 A2 EP 2102290A2 EP 07818528 A EP07818528 A EP 07818528A EP 07818528 A EP07818528 A EP 07818528A EP 2102290 A2 EP2102290 A2 EP 2102290A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- pigment
- radical
- pigment preparation
- sub
- group
- 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- Withdrawn
Links
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- 238000002360 preparation method Methods 0.000 claims abstract description 56
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- 239000000654 additive Substances 0.000 claims abstract description 9
- 230000000996 additive effect Effects 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims abstract description 7
- 239000002270 dispersing agent Substances 0.000 claims abstract description 5
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- 239000003755 preservative agent Substances 0.000 claims abstract description 3
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- -1 Fiammschutzmittei Substances 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 239000000976 ink Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
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- 238000007639 printing Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 150000003254 radicals Chemical class 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
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- 125000001424 substituent group Chemical group 0.000 claims description 7
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 4
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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
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 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 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
- 150000004056 anthraquinones Chemical class 0.000 claims description 3
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 claims description 3
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- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 claims description 3
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 3
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- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 claims description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 3
- 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 3
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- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000000751 azo group Chemical group [*]N=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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- 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
- 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 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
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- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical class [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- VYXSBFYARXAAKO-UHFFFAOYSA-N ethyl 2-[3-(ethylamino)-6-ethylimino-2,7-dimethylxanthen-9-yl]benzoate;hydron;chloride Chemical compound [Cl-].C1=2C=C(C)C(NCC)=CC=2OC2=CC(=[NH+]CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-UHFFFAOYSA-N 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000006358 imidation reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 235000014569 mints Nutrition 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229940104573 pigment red 5 Drugs 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical class [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
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
- 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
- C09B67/006—Preparation of organic pigments
- C09B67/0063—Preparation of organic pigments of organic pigments with only macromolecular substances
-
- 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
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0002—Grinding; Milling with solid grinding or milling assistants
-
- 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
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0004—Coated particulate pigments or dyes
- C09B67/0008—Coated particulate pigments or dyes with organic coatings
- C09B67/0013—Coated particulate pigments or dyes with organic coatings with polymeric coatings
-
- 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
- C09B67/006—Preparation of organic pigments
-
- 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
- C09D11/16—Writing inks
- C09D11/17—Writing inks characterised by colouring agents
-
- 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
- C09D11/16—Writing inks
- C09D11/18—Writing inks specially adapted for ball-point writing instruments
-
- 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
-
- 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
- C09D11/34—Hot-melt inks
-
- 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
- C09D11/36—Inkjet printing inks based on non-aqueous solvents
-
- 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
- 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
-
- 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
- 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
-
- 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 is readily dispersible
- Pigment preparations of at least one pigment and an additive based on Polyalkylengiykoien also relates to the process for their preparation and their use for coloring natural and synthetic materials, in particular paints, coating systems, dispersion and enamel paints of all kinds.
- Dispersing pigments into an application system is a critical and expensive process. Easily dispersible pigment preparations or stir-in pigments can be incorporated into the application system in comparison to conventional pigments with significantly lower energy input and higher and faster color development, which is of great economic advantage.
- WO 2004/074 383 discloses stir-in pigments which are easy to disperse exclusively in solvent-containing application media.
- EP-A1-1 132434 discloses the preparation of organic readily dispersible pigments through the use of dispersants based on aromatic polyalkylene polymers. These stir-in pigments are compatible only with aqueous application systems. There is a need for pigment preparations which have easy dispersibility both in aqueous and in solvent-containing application media. Such stir-in pigments should be universally compatible and their incorporation should be carried out just as easily and without additional steps, regardless of the application medium. Easily dispersible means that the pigment can incorporate into the application system with very low energy input and high and rapid color development. Gentle effects, such as the effect of a dissolver (sawtooth stirrer), are sufficient to achieve complete dispersion of the pigment, so that it is possible to dispense with further cost-intensive dispersing steps in the application system.
- pigment preparations based on organic or inorganic pigments and specific polyalkylene glycols as defined below can be easily dispersed both in aqueous and in solvent-containing application media.
- the invention therefore provides a pigment preparation comprising (a) 50 to 99% by weight, preferably 70 to 97.5% by weight, of at least one pigment, (b) 1 to 50% by weight, preferably 2.5 to 30 wt .-%, of an additive based on polyalkylene glycols, and
- AO represents a C 2 -C 0 alkyleneoxy moiety, where A may be the same or different when n is greater than 1,
- B is a C 2 -C 10 -alkylene radical
- T is -NR 1 -
- R 1 is a direct covalent bond to X, or is a hydrogen atom, a C 1 -C 18 alkyl radical, a C 3 -C 7 cycloalkyl radical, benzyl, or a substituted or unsubstituted C 6 -C 8 aryl radical, said substituents being the Significance Halogen, especially fluorine, chlorine or bromine, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, butoxy, nitro or CF 3 have X for one of the groups
- R is a hydrogen atom, a Ci-C-is-alkyl radical, a C 3 -C 7 -cycloalkyl radical, benzyl, or a substituted or unsubstituted C 6 -C 8 -aryl radical, where the substituents are halogen, in particular fluorine, chlorine or Bromine, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, butoxy, nitro or CF 3 ;
- R 2 is a C 1 -C 8 -alkylene radical, a C 3 -C 7 -cycloalkylene radical, a substituted or unsubstituted C 6 -C 6 -arylene radical, or a meaningful chemical combination thereof, and the substituents are halogen, in particular fluorine, chlorine or bromine, methyl, ethyl, propyl, butyl,
- Y is a chemical bond or -NR 3 -, wherein R 3 has one of the meanings given for R 1 ;
- Z is an amino group, or a radical of a carboxylic acid or a carboxylic acid derivative on which the group XY is based, such as, for example, anhydride, acid chloride, ester, or a radical of an isocyanate on which the group XY is based,
- Z is a radical of an amine underlying the group (AO) n -B, or a radical of a carboxylic acid or a carboxylic acid derivative on the group X, such as, for example, anhydride, acid chloride, ester, or a radical of an isocyanate underlying the group X.
- n is a number between 1 and 200, for example 2 to 150; and m is a number between 1 and 100, for example 2 to 50, in particular 2 to 10, means.
- 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 insoluble in certain solvents and has this pigment character.
- the pigments can be used both in the form of dry powder and as water-moist press cake.
- organic pigments there are monoazo, disazo, laked azo, ⁇ -naphthol, naphthol AS, benzimidazolone, disazo condensation, azo metal complex pigments and polycyclic pigments, e.g.
- organic pigments mentioned those are particularly suitable which are as finely divided as possible for the production of the preparations, wherein preferably 95% and particularly preferably 99% of the pigment particles have a particle size ⁇ 500 nm.
- organic pigments are carbon black pigments, such as 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 97, 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 II, 214, Pigment Red Red, 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 AS pigments, in particular the Color Index pigments Pigment Red 2, Pigment Red 3, Pigment
- Suitable inorganic pigments are, for example, titanium dioxides, zinc sulfides,
- Zinc oxides iron oxides, manganese iron oxides, chromium oxides, ultramarine, nickel or chromium antimony titanium oxides, cobalt oxides, mixed oxides of cobalt and aluminum,
- Rutile mixed phase pigments rare earth sulphides, bismuth vanadates and
- the organic pigment is preferably combined with carbon black and / or titanium dioxide.
- laked dyes such as Ca, Mg, Al lacquers of dyes containing sulfonic acid and / or carboxylic acid groups.
- Preferred polyalkylene glycols are those of formula (1), wherein
- AO represents an ethyleneoxy (EO) unit, propyleneoxy (PO) unit or a combination thereof.
- EO and PO units can be arranged alternately, blockwise or statistically.
- Preferred polyalkylene glycols are furthermore those of the formula (1), where
- B is an ethylene or propylene radical.
- Preferred polyalkylene glycols are furthermore those of the formula (1) where R 1 or R 3 is a direct covalent bond to X, a hydrogen atom, a C 1 -C 4 -
- Alkyl radical a Cs-Ce-cycloalkyl radical or phenyl.
- Preferred polyalkylene glycols are furthermore those of the formula (1), where
- R is a hydrogen atom, C 1 -C 4 -alkyl radical, C 5 -C 6 -cycloalkyl radical or phenyl.
- Preferred polyalkylene glycols are further those of formula (1), wherein R 2 is a Ci-Ci 2 alkylene radical, a C 5 -C 6 cycloalkylene, a substituted or unsubstituted C 6 -C o-arylene, wherein the substituents have the mentioned
- Preferred polyalkylene glycols are furthermore those of the formula (1) in which X is one of the groups
- R is a hydrogen atom
- R 2 is a Ci-Ci 2 alkylene radical or an unsubstituted C 6 -C O arylene.
- R 1 is a hydrogen atom or a direct covalent bond to X
- R is a hydrogen atom
- R 2 is a Ci-C, 2 alkylene or unsubstituted C 6 -C 0 arylene radical
- Y is a chemical bond or -NR 3 -, wherein R 3 is a hydrogen atom or a direct covalent Bindu Z and Z 'have the abovementioned meaning, and m is a number between 2 and 30.
- Z and Z ' are end groups of the polyalkylene glycols of the formula (1) and may be amino groups, isocyanate groups or radicals of a carboxylic acid which can be derivatized by known reactions. These reactions may be e.g. Alkylations, amidations, halogenations, hydrolysis, esterifications, condensations, saponifications, imidations or suifonations.
- the polyalkylene glycols of the formula (1) may also be mixtures having different end groups Z and Z ', as are formed, for example, from the following reaction:
- polyalkylene glycols used according to the invention can be prepared analogously to the methods described in US Pat. No. 5,324,812, US Pat. No. 4,761,465 or WO 94/12986 (EP-O 672 291 B1). However, they have hitherto not been used as dispersing agents for pigments or have not been described with pigment preparations containing such polyalkylene glycols.
- auxiliaries described as component (c) are known to the person skilled in the art and can be used in the amounts mentioned in the invention
- Pigment preparations are added without affecting the stir-in properties of the pigment preparation.
- the adjuvants differ structurally from the polyalkylene glycols of formula (1).
- the pigment preparation according to the invention is in powder form or granules and preferably has a particle size d 50 of 0.03 to 0.60 ⁇ m. Granules can be obtained, for example, by spray drying.
- the present invention also provides a process for the preparation of the inventive pigment preparations, characterized in that the component (a) in the form of powder, granules or presscake in the presence of water or an organic solvent or a mixture of water and organic solvent with the Component (b) and optionally the component (c) mixed.
- a particularly advantageous mixing can be achieved by the use of a Mahloder 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 milling of the pigments 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, suitably at a temperature between 10 and 70 0 C, preferably at 20 to 6O 0 C.
- the obtained pigment suspension may be subjected to a finish.
- the finish is expediently in the present organic solvent, water or water-solvent mixture at a temperature of 50 to 25O 0 C 1 especially 70 to 200 ° C, especially 100 to 190 0 C, and suitably for a period of 5 minutes to 24 hours, especially 5 minutes to 18 hours, especially 5 minutes to 6 hours.
- the finish is preferably carried out at boiling temperature, in particular at temperatures above the boiling point of the solvent system under pressure. For organic solvents which can be separated from the aqueous phase by steam distillation, it is advisable to remove them in this way from isolation of the pigment preparation, especially if recovery of the solvent used is desired.
- the pigment preparations prepared by the process according to the invention can be isolated by the customary methods, for example by filtration, decantation, centrifugation, spray drying, fluidized bed drying, belt drying, spray granulation or drying in a paddle dryer.
- the Isolation of the pigment preparations according to the invention is preferably carried out by filtration and final drying. If the pigment preparation obtained is coarse-grained, it is expediently subjected to dry grinding.
- the pigment preparations according to the invention are suitable for pigmenting and dyeing natural and synthetic materials of any kind, in particular paints, brush systems, such as wallpaper paints, printing inks, dispersion and enamel paints, which contain water and / or solvents. Furthermore, the pigment preparations according to the invention are suitable for coloring macromolecular materials of all kinds, e.g. of natural and synthetic fiber materials, preferably cellulose fibers, also for paper pulp dyeing and for laminating dyeing. Further applications are the production of printing inks, in this case for example textile printing, flexographic printing, decorative printing or gravure printing inks, wallpaper paints, water-dilutable paints,
- Wood protection systems viscose spin dyes, paints, sausage casings, seeds, fertilizers, glass, especially glass bottles, and for mass coloration of roof tiles, as colorants in electrophotographic toners and developers, for coloring for plasters, concrete, wood stains, crayon mints, felt-tip pens, waxes, paraffins, Tushes, pastes for pens, chalks, detergents and cleaners, shoe care products, latex products, abrasives and for coloring plastics or high molecular weight materials of all kinds.
- High molecular weight organic materials are, for example, cellulose ethers and esters, such as ethylcellulose, nitrocellulose, cellulose acetate or cellulose butyrate , natural resins or synthetic resins, such as polymerization or condensation resins, eg Aminoplasts, in particular urea- and melamine-formaldehyde resins, alkyd resins, acrylic resins, phenoplasts, 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.
- cellulose ethers and esters such as ethylcellulose, nitrocellulose, cellulose acetate or cellulose butyrate
- natural resins or synthetic resins such as polymerization or condensation resins, eg Aminoplasts
- the pigment preparations according to the invention are suitable for the production of printing inks for use in all conventional ink jet printers. Printers, in particular for those based on the bubble jet or piezo method. 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 of coated or uncoated substrate materials, for example for printing on cardboard, cardboard, wood and wood-based materials, metallic materials, semi-ferriterias, 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 suitable as colorants for powders and powder coatings, in particular for triboelectrically or elektroki net sprayable powder coatings, which are used for surface coating of objects made of, for example, metal, wood, plastic, glass, ceramic, concrete, textile, paper or rubber.
- the pigment preparations of the present invention are useful as colorants in inks, preferably ink-jet inks, e.g. aqueous or non-aqueous based ("solvent based"), microemulsion inks, UV curable inks, as well as in those inks that work according to the hot-melt process suitable.
- ink-jet inks e.g. aqueous or non-aqueous based ("solvent based"), microemulsion inks, UV curable inks, as well as in those inks that work according to the hot-melt process suitable.
- pigment preparations according to the invention are also suitable as colorants for "color filter” for "Fiat panel displays”, both for the additive and the subtractive color generation, also for “photo-resists”, as well as colorants for electronic inks (" Electronic Inks “or” e-inks ”) or electronic paper (“ Electronic Paper “or” e-paper “).
- the invention also provides a process for dyeing a high molecular weight organic material which comprises uniformly dispersing an effectively pigmenting amount of a stir-in pigment preparation according to the invention in the organic material by stirring in the organic material Pigment preparation in a suspension or solution of the organic material.
- Stirring is understood as meaning any kind of mixing using low shear forces, eg also shaking.
- An effective pigmenting amount is usually between 0.01 and 30 wt .-% pigment preparation, based on the weight of the organic material to be pigmented.
- M20 universal mill, IKA, 2 times 15 sec 35 g of readily dispersible powdery pigment red 122 are obtained.
- a suspension of 139 g of Pigment Violet 23 (Cl.No .: 51319), used as a vibratory grind with a pigment content of 73.6% by weight and a BET surface area of 2.4 m 2 / g, in 250 g of water and 300 g g isobutanol is, after addition of 56.6 g of polyalkylene glycol of formula 1.2, dispersed in a static mixer (Laborpilot 2000, IKA, D-79219 Staufen) for 15 minutes at 6000 rpm. The mixture is subjected to a pressure finish for 3 hours at 130 0 C.
- Pigment Yellow 139 (Cl.No. 56298, used as a 32% strength by weight presscake) in 480 g of water.
- 6.6 g of polyalkylene glycol of the formula 1.2 are added.
- the mixture is subjected to a pressure finish for 4 hours at 140 0 C.
- the occupied pigment is filtered off, washed with water and dried at 8O 0 C inkowskischra ⁇ k.
- After a dry milling (M20 universal mill, IKA, 2 times 15 sec), 50 g of readily dispersible powdered pigment Yellow 139 are obtained.
- Pigment Yellow 139 (Cl.No. 56298, used as a 32% strength by weight presscake) in 480 g of water.
- 6.6 g of polyalkylene glycol of the formula 1.1 are added.
- the mixture is subjected to a pressure finish for 4 hours at 14O 0 C.
- the occupied pigment is filtered off, washed with water and dried at 80 0 C in a drying oven.
- 50 g of readily dispersible powdered pigment Yellow 139 are obtained.
- the pigment preparations are tested in a solvent-based alkyd melamine stoving lacquer (AM lacquer) and in an aqueous polyester melamine stoving lacquer (WPM lacquer).
- AM lacquer solvent-based alkyd melamine stoving lacquer
- WPM lacquer aqueous polyester melamine stoving lacquer
- the pigments ⁇ Hostaperm Pink E (PR 122), Hostaperm Violet RL spezial (PV 23) and ⁇ Novoperm Orange HL 70 (PO36) and ® Novoperm Yellow M2R70 (PY 139) from Clariant, in the above-mentioned coating systems with the Dissolver dispersed and with the pigment preparations from Examples 1 to 7 compared.
- the determined color strength shows that the pigment preparations according to the invention develop a much higher color strength in both coating systems, both in the solvent-containing alkyd-melamine lacquer and in the aqueous polyester-melamine lacquer.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Polyethers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102006052139A DE102006052139A1 (de) | 2006-11-06 | 2006-11-06 | Universelle Stir-in Pigmente |
| PCT/EP2007/008445 WO2008055566A2 (de) | 2006-11-06 | 2007-09-28 | Universelle stir-in pigmente |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP2102290A2 true EP2102290A2 (de) | 2009-09-23 |
Family
ID=39246858
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP07818528A Withdrawn EP2102290A2 (de) | 2006-11-06 | 2007-09-28 | Universelle stir-in pigmente |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7833343B2 (enExample) |
| EP (1) | EP2102290A2 (enExample) |
| JP (1) | JP2010508406A (enExample) |
| KR (1) | KR20090083359A (enExample) |
| CN (1) | CN101535415A (enExample) |
| DE (1) | DE102006052139A1 (enExample) |
| WO (1) | WO2008055566A2 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008054391B4 (de) | 2008-12-08 | 2019-03-07 | Wacker Chemie Ag | Partikuläre Zubereitungen mit Dispergierhilfsmitteln und Verfahren zur Herstellung der Zubereitungen |
| CN102002866B (zh) * | 2010-11-02 | 2012-11-14 | 华纺股份有限公司 | 一种真蜡服装面料的变色印花工艺 |
| CN104250413B (zh) * | 2013-06-28 | 2016-05-11 | 步步高教育电子有限公司 | 一种高分子材料笔芯及铅笔 |
| EP3114173A4 (en) | 2014-03-05 | 2018-01-03 | DRIKOLOR Inc | Easily dispersible formulations of pigments and their use in tinting base media |
| JP6894953B2 (ja) * | 2014-11-04 | 2021-06-30 | クラリアント・インターナシヨナル・リミテツド | Ｃ．ｉ．ピグメントイエロー１５５とその製造方法、その顔料を用いた顔料組成物と着色剤組成物、及びそれらの着色剤としての使用 |
| US9718737B2 (en) | 2015-04-21 | 2017-08-01 | Behr Process Corporation | Decorative coating compositions |
| BR112017024008A2 (pt) * | 2015-05-12 | 2018-07-17 | Rhodia Operations | auxiliares da dispersão ou suas combinações para preparar corantes universais para tintas e revestimento aquosos e não aquosos |
| DE102015211827A1 (de) * | 2015-06-25 | 2016-12-29 | Clariant International Ltd | Neue Naphthol AS-Pigmente |
| CN107022215B (zh) * | 2017-03-31 | 2019-07-12 | 福建惠安霞飞石雕工艺有限公司 | 一种砗磲的加工工艺及其彩绘颜料 |
| CN107956150A (zh) * | 2017-11-20 | 2018-04-24 | 安徽华美新材料科技有限公司 | 一种高效环保级阻燃染色料制备方法 |
| US12091556B2 (en) | 2018-02-14 | 2024-09-17 | Tronox Llc | Stir-in titanium dioxide pigment composition |
| CN111718610A (zh) * | 2020-07-24 | 2020-09-29 | 蓬莱新光颜料化工有限公司 | 一种阻燃颜料及其制备方法 |
| JP7474204B2 (ja) * | 2021-01-28 | 2024-04-24 | 日信化学工業株式会社 | 塗料組成物、家具及び建築内装用塗料組成物、並びに積層体 |
| JP7474205B2 (ja) * | 2021-01-28 | 2024-04-24 | 日信化学工業株式会社 | 外壁及び建築外装用塗料組成物、並びに積層体 |
| CN115403938B (zh) * | 2022-09-22 | 2024-02-09 | 浙江纳美新材料股份有限公司 | 一种用于化肥染色的有机颜料色浆及其制备方法和应用 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4761465A (en) * | 1987-07-27 | 1988-08-02 | Texaco Inc. | Difunctional isocyanate-terminated polyoxyalkylene diamine prepolymers and polymer coatings applications |
| CA2057335A1 (en) | 1991-08-26 | 1993-02-27 | Dudley J. Ii Primeaux | Quasi-prepolymers of aliphatic diisocyanates and polyoxyalkylene polyamine mixtures useful for making polyurea elastomers |
| FR2698631B1 (fr) | 1992-12-01 | 1995-02-10 | Centre Nat Rech Scient | Copolymères à propriétés rédox et leur utilisation pour l'élaboration de matériaux à conduction mixte. |
| US5883220A (en) | 1992-01-12 | 1999-03-16 | Centre National De La Recherche Scientifique | Redox copolymers and their use in preparing mixed conduction materials |
| US5324812A (en) * | 1993-04-01 | 1994-06-28 | Texaco Chemical Company | Water soluble polyamide from polyalkylene glycol diamines and polycarboxylic acids |
| US5648408A (en) * | 1995-06-07 | 1997-07-15 | Ciba-Geigy Corporation | Organic stir-in pigments |
| US6063182A (en) * | 1997-09-08 | 2000-05-16 | Ciba Speciality Chemicals Corporation | Stir-in pigment compositions |
| DE19826624A1 (de) * | 1998-06-18 | 1999-12-23 | Merck Patent Gmbh | Pigmentpräparation |
| US6440207B1 (en) * | 2000-03-03 | 2002-08-27 | Bayer Corporation | Method for preparing organic pigments |
| EP1474485B2 (de) * | 2002-02-04 | 2015-11-04 | Basf Se | Pigmentzubereitungen |
| DE10204583A1 (de) | 2002-02-04 | 2003-08-07 | Basf Ag | Pigmentzubereitungen |
| KR20050103950A (ko) | 2003-02-20 | 2005-11-01 | 시바 스페셜티 케미칼스 홀딩 인크. | 내부 교반 안료 조성물 |
| DE102006021178A1 (de) * | 2006-05-06 | 2007-11-08 | Clariant International Limited | VOC-arme Feuchthaltemittel für wässrige Pigmentpräparationen |
| US20100075161A1 (en) * | 2007-02-26 | 2010-03-25 | Akzo Nobel N.V. | Pigment Composition |
-
2006
- 2006-11-06 DE DE102006052139A patent/DE102006052139A1/de not_active Withdrawn
-
2007
- 2007-09-28 KR KR1020097009200A patent/KR20090083359A/ko not_active Withdrawn
- 2007-09-28 EP EP07818528A patent/EP2102290A2/de not_active Withdrawn
- 2007-09-28 CN CNA2007800411543A patent/CN101535415A/zh active Pending
- 2007-09-28 WO PCT/EP2007/008445 patent/WO2008055566A2/de not_active Ceased
- 2007-09-28 JP JP2009534995A patent/JP2010508406A/ja not_active Withdrawn
- 2007-09-28 US US12/513,442 patent/US7833343B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2008055566A2 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101535415A (zh) | 2009-09-16 |
| WO2008055566A3 (de) | 2009-02-12 |
| KR20090083359A (ko) | 2009-08-03 |
| US20100068642A1 (en) | 2010-03-18 |
| WO2008055566A2 (de) | 2008-05-15 |
| US7833343B2 (en) | 2010-11-16 |
| DE102006052139A1 (de) | 2008-05-08 |
| JP2010508406A (ja) | 2010-03-18 |
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