EP1874833A1 - Polymer for the dispersion of pigments and fillers - Google Patents
Polymer for the dispersion of pigments and fillersInfo
- Publication number
- EP1874833A1 EP1874833A1 EP06742705A EP06742705A EP1874833A1 EP 1874833 A1 EP1874833 A1 EP 1874833A1 EP 06742705 A EP06742705 A EP 06742705A EP 06742705 A EP06742705 A EP 06742705A EP 1874833 A1 EP1874833 A1 EP 1874833A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- polymer
- group
- groups
- pigments
- dispersant
- 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- Withdrawn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
- 229920000642 polymer Polymers 0.000 title claims abstract description 66
- 239000000049 pigment Substances 0.000 title claims abstract description 42
- 239000000945 filler Substances 0.000 title claims abstract description 9
- 239000006185 dispersion Substances 0.000 title description 8
- 239000002270 dispersing agent Substances 0.000 claims abstract description 22
- 239000000178 monomer Substances 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 238000010526 radical polymerization reaction Methods 0.000 claims description 5
- 239000008199 coating composition Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 238000000465 moulding Methods 0.000 claims 1
- 239000003973 paint Substances 0.000 abstract description 10
- 239000002245 particle Substances 0.000 description 22
- -1 therefore Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000004062 sedimentation Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 229910010413 TiO 2 Inorganic materials 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UPIWXMRIPODGLE-UHFFFAOYSA-N butyl benzenecarboperoxoate Chemical compound CCCCOOC(=O)C1=CC=CC=C1 UPIWXMRIPODGLE-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000002270 phosphoric acid ester group Chemical group 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 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 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- 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
- C09D5/02—Emulsion paints including aerosols
- C09D5/024—Emulsion paints including aerosols characterised by the additives
- C09D5/027—Dispersing 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/45—Anti-settling agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
Definitions
- the invention relates to a polymer which can be used as a dispersant, a process for the preparation of the polymer and the use of the polymer as a dispersant, in particular for pigments and fillers, for example.
- pigment pastes and coating compositions such as paints and varnishes.
- pigment particles which are contained in these must form a stable dispersion, ie be distributed homogeneously and as small as possible primary particles.
- the dispersed pigment particles on the one hand must be well wetted by the solvent, on the other hand, the pigment particles must be prevented from re-agglomeration, so that formation of larger agglomerates is suppressed, which would rapidly decrease in the solvent.
- the surface of pigment particles or of the fillers used in the coating composition can range from very polar to very nonpolar. In order to achieve compatibilization of the particles with the solvent or binder, therefore, dispersants are used. These must be on the one hand with the surface - -
- the dispersant must therefore have in the molecule areas that are well compatible with the solvent or binder. If organically based systems are used, for example hydrophobic structures, such as alkyl, polyester or aryl groups, can be provided in the molecule of the dispersant.
- the compatibilizing portion is usually composed of polyethylene glycols or of polymerized monomers having (salified) carboxylic acid groups.
- the polar surface of an inorganic pigment particle may be coated with a polymer having polar portions that bind to the polar surface of the particle, as well as nonpolar portions that provide compatibility with the solvent.
- Polar regions can be generated, for example, by providing in the polymer (tertiary) amino groups, phosphoric acid ester groups or carboxylic acid groups.
- the polar surface of the pigment particle is therefore coated with a shell, which has more non-polar properties compared to the surface of the pigment particle.
- the surface of the pigment particles thus becomes more similar in polarity to that of the solvent or binder. In this way, the pigment particles can be wetted by the solvent and dispersed so that they are homogeneous and finely divided, do not float on the solvent and do not settle.
- the polymer also contains sterically demanding groups which hinder the individual pigment particles from agglomerating due to steric hindrance.
- EP 1197 536 A2 describes a composition which can be used as a dispersant for pigments.
- the composition contains a graft polymer having an average molecular weight of about 5,000 - 100,000 and that Polymer backbone, as well as derived from the backbone anionic and nonionic hydrophilic side chains. Compared to the side chains, the polymer backbone has hydrophobic properties and contains polymerized ethylenically unsaturated hydrophobic monomers and, based on the total weight of the polymer backbone, in an amount of up to 30% by weight of polymerized ethylenically unsaturated monomers carrying functional groups can increase the binding power of pigments.
- the anionic side chains are formed by hydrophilic macromonomers prepared from polymerized ethylenically unsaturated monomers and containing, based on the total weight of the anionic side chain, 2-100% by weight of a polymerized ethylenically unsaturated acidic monomer.
- the nonionic side chains are formed by hydrophilic ethylenically unsaturated macromonomers containing polyalkylene glycols.
- EP 1 293 523 A2 describes a water-based pigment dispersion which can be used for the production of aqueous compositions for coatings and which contains a dispersed pigment, an aqueous carrier and as dispersant a branched polymer.
- the polymer used as a dispersant has a weight average molecular weight of about 5,000 to 100,000 and comprises 20 to 80% by weight of a hydrophilic backbone and 80 to 20% by weight of macromonomer side chains.
- EP 0 311 157 A1 describes a polymer which can be used as a dispersant. It is composed of (A) 0 to 80 mol% of a styrene derivative, (B) 0 to 70 mol% of an acrylate or methacrylate derivative, (C) 5 to 50 mol% of a monomer containing a heterocyclic group containing at least one basic nitrogen atom in the ring, (D) 0-10 mol% of a monomer comprising a group capable of causing cross-linking or coupling, and 0 to 20 mol% of a monomer not included in the groups (A ) to (D), wherein the proportion of the monomers of group (A) and the monomers having an acrylate group at least 20 mol%.
- R> 5 H or an alkyl group having 1 to 6 carbon atoms
- Non-polar groups are introduced into the polymer via the repeating unit indicated by the index b via the group R 3 .
- An aralkyl group is understood as meaning an aryl group which is substituted by at least one alkyl group or alkylene group, such as a methyl group or a methylene group.
- R 3 is particularly preferably a phenyl group or a phenyl group substituted by one or more methyl or isobutyl groups.
- R 1 , R 2 , R 3 , R 4 , a, b and c have the abovementioned meaning.
- the polymerization can be carried out batchwise, d. H. the starting materials are initially charged in a reaction vessel and the reaction started by addition of a radical initiator. However, it is also possible to carry out the reaction in the feed process, all or part of the educts being introduced into the reaction vessel during the reaction.
- Fig. 3 is a graphical representation of the orientation parameters for Iriodin 225 ® in an aqueous acrylate paint upon addition of the polymer of the invention
- Fig. 4 is a graphical representation of the orientation parameters for Iriodin 225 ® in a solvent-based polyurethane paint upon addition of the polymer of the invention.
- the sedimentation of the pigments could be slowed down.
- the degree of stabilization also depends on the concentration of the polymer.
- the orientation parameter L25 / L75 was used, wherein L25 and L75 were determined colorimetrically at the angles 25 ° and 75 ° in the gyroscopic method. The larger and more uniform the orientation parameter, the better the horizontal orientation of the pigment particles. Ideally, the values of the orientation parameter form a circle. The results of the measurements of the orientation parameter are shown in FIGS. 3 and 4.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Paints Or Removers (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102005019384A DE102005019384A1 (en) | 2005-04-26 | 2005-04-26 | New polymer useful as dispersion agent for pigment and fillers; and in coating agent, pastes and/or molding material |
PCT/EP2006/003880 WO2006114303A1 (en) | 2005-04-26 | 2006-04-26 | Polymer for the dispersion of pigments and fillers |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1874833A1 true EP1874833A1 (en) | 2008-01-09 |
Family
ID=36592878
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP06742705A Withdrawn EP1874833A1 (en) | 2005-04-26 | 2006-04-26 | Polymer for the dispersion of pigments and fillers |
Country Status (6)
Country | Link |
---|---|
US (1) | US20080293874A1 (en) |
EP (1) | EP1874833A1 (en) |
JP (1) | JP2008539289A (en) |
CA (1) | CA2595823A1 (en) |
DE (1) | DE102005019384A1 (en) |
WO (1) | WO2006114303A1 (en) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102007021869A1 (en) * | 2007-05-10 | 2008-11-13 | Clariant International Limited | Anionic water-soluble additives |
DE102007021870A1 (en) * | 2007-05-10 | 2008-11-20 | Clariant International Limited | Aqueous pigment preparations |
DE102007021868A1 (en) | 2007-05-10 | 2008-11-20 | Clariant International Limited | Nonionic water-soluble additives |
WO2010003867A1 (en) * | 2008-07-08 | 2010-01-14 | Huntsman International Llc | Dispersant for dispersing matter comprising gypsum |
DE102008038071A1 (en) | 2008-08-16 | 2010-02-18 | Clariant International Limited | Anionic water- and solvent-soluble additives |
DE102008037973A1 (en) | 2008-08-16 | 2010-02-18 | Clariant International Limited | Dry pigment preparations with anionic additives |
DE102008038070A1 (en) | 2008-08-16 | 2010-02-18 | Clariant International Ltd. | Dry pigment preparations with nonionic additives |
DE102008038072A1 (en) | 2008-08-16 | 2010-02-18 | Clariant International Ltd. | Nonionic water and solvent soluble additives |
CN104558431B (en) * | 2013-10-28 | 2018-05-18 | 广东华润涂料有限公司 | The dispersion of water-based latex and inorganic pigment granules comprising the water-based latex |
CN105330791A (en) * | 2015-10-28 | 2016-02-17 | 武汉理工大学 | Preparing method of surfactant for stripping compatibility-controllable oxidized graphene |
CN105778573B (en) * | 2016-05-03 | 2018-08-14 | 江苏妙润新材料科技有限公司 | A kind of hyper-dispersant and preparation method thereof and application method |
CN111690100B (en) * | 2020-07-03 | 2021-03-16 | 广州市克来斯特建材科技有限公司 | Polycarboxylic acid water-reducing mother liquor and preparation method thereof |
EP4092088A1 (en) * | 2021-05-20 | 2022-11-23 | Clariant International Ltd | Universal dispersing agent for inorganic and organic pigments |
CN113278111B (en) * | 2021-05-27 | 2023-05-02 | 浙江理工大学 | Preparation method of terpolymer dispersing agent and application of terpolymer dispersing agent in preparation of liquid disperse dye |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9208535D0 (en) * | 1992-04-21 | 1992-06-03 | Ici Plc | Co-polymers |
US5504133A (en) * | 1993-10-05 | 1996-04-02 | Mitsubishi Materials Corporation | Composition for forming conductive films |
DE4435376B4 (en) * | 1993-10-05 | 2004-11-11 | Dai Nippon Toryo Co., Ltd. | Composition for forming conductive films |
US7008992B1 (en) * | 1998-07-22 | 2006-03-07 | E. I. Du Pont De Nemours And Company | Water insoluble non-ionic graft copolymers |
DE19942301A1 (en) * | 1999-09-04 | 2001-03-08 | Basf Ag | Cement-based composition for use e.g. as repair mortar or tile adhesive, contains an acrylic copolymer with lower alkyl-terminated polyethoxy-acrylate or -methacrylate comonomer units |
US6528593B1 (en) * | 1999-09-10 | 2003-03-04 | The Dow Chemical Company | Preparing copolymers of carboxylic acid, aromatic vinyl compound and hydrophobic polyalkylene oxide |
EP1510556B1 (en) * | 2003-08-27 | 2013-02-13 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Dispersants for organic pigments |
-
2005
- 2005-04-26 DE DE102005019384A patent/DE102005019384A1/en not_active Withdrawn
-
2006
- 2006-04-26 JP JP2008508149A patent/JP2008539289A/en active Pending
- 2006-04-26 WO PCT/EP2006/003880 patent/WO2006114303A1/en active Application Filing
- 2006-04-26 EP EP06742705A patent/EP1874833A1/en not_active Withdrawn
- 2006-04-26 CA CA002595823A patent/CA2595823A1/en not_active Abandoned
- 2006-04-26 US US11/912,337 patent/US20080293874A1/en not_active Abandoned
Non-Patent Citations (1)
Title |
---|
See references of WO2006114303A1 * |
Also Published As
Publication number | Publication date |
---|---|
JP2008539289A (en) | 2008-11-13 |
WO2006114303A1 (en) | 2006-11-02 |
CA2595823A1 (en) | 2006-11-02 |
US20080293874A1 (en) | 2008-11-27 |
DE102005019384A1 (en) | 2006-11-02 |
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