CA2430991C - Pigment dispersion and method of preparing the same - Google Patents

Pigment dispersion and method of preparing the same Download PDF

Info

Publication number: CA2430991C
Authority: CA; Canada
Prior art keywords: methacrylate; set forth; group; acrylic emulsion; acrylate
Prior art date: 2000-12-22
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.): Expired - Fee Related

Application number

CA 2430991

Other languages

English (en)

French (fr)

Other versions

CA2430991A1 (en

Inventor

Swaminathan Ramesh

Joann Lanza

Paul Harris

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF Corp

Original Assignee

BASF Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-12-22

Filing date

2001-11-19

Publication date

2008-08-05

2001-11-19 Application filed by BASF Corp filed Critical BASF Corp

2002-07-04 Publication of CA2430991A1 publication Critical patent/CA2430991A1/en

2008-08-05 Application granted granted Critical

2008-08-05 Publication of CA2430991C publication Critical patent/CA2430991C/en

2021-11-19 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000000049 pigment Substances 0.000 title claims abstract description 78
239000006185 dispersion Substances 0.000 title claims abstract description 43
238000000034 method Methods 0.000 title claims abstract description 31
239000000839 emulsion Substances 0.000 claims abstract description 111
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 106
239000002270 dispersing agent Substances 0.000 claims abstract description 106
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims abstract description 55
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 43
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims abstract description 32
229920000137 polyphosphoric acid Polymers 0.000 claims abstract description 32
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 26
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims abstract description 16
239000001023 inorganic pigment Substances 0.000 claims abstract description 15
239000007795 chemical reaction product Substances 0.000 claims abstract description 13
239000002202 Polyethylene glycol Substances 0.000 claims abstract description 6
229920001427 mPEG Polymers 0.000 claims abstract description 6
229920001223 polyethylene glycol Polymers 0.000 claims abstract description 6
239000000178 monomer Substances 0.000 claims description 175
239000002253 acid Substances 0.000 claims description 72
229920001515 polyalkylene glycol Polymers 0.000 claims description 67
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 61
239000000203 mixture Substances 0.000 claims description 54
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 36
239000004908 Emulsion polymer Substances 0.000 claims description 32
-1 aliphatic acrylates Chemical class 0.000 claims description 29
150000002430 hydrocarbons Chemical class 0.000 claims description 29
239000004215 Carbon black (E152) Substances 0.000 claims description 28
229930195733 hydrocarbon Natural products 0.000 claims description 28
239000011541 reaction mixture Substances 0.000 claims description 25
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 22
150000001412 amines Chemical class 0.000 claims description 18
150000001450 anions Chemical group 0.000 claims description 15
150000001875 compounds Chemical class 0.000 claims description 12
229920000642 polymer Polymers 0.000 claims description 11
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 10
239000003945 anionic surfactant Substances 0.000 claims description 10
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
239000012972 dimethylethanolamine Substances 0.000 claims description 8
150000001252 acrylic acid derivatives Chemical class 0.000 claims description 6
150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 6
GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 5
JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 claims description 5
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 5
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
229960002887 deanol Drugs 0.000 claims description 5
150000001991 dicarboxylic acids Chemical class 0.000 claims description 5
GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 claims description 5
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 5
LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 claims description 5
LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims description 5
PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 5
HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 claims description 5
KCAMXZBMXVIIQN-UHFFFAOYSA-N octan-3-yl 2-methylprop-2-enoate Chemical compound CCCCCC(CC)OC(=O)C(C)=C KCAMXZBMXVIIQN-UHFFFAOYSA-N 0.000 claims description 5
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 5
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 5
NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims description 5
PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims description 5
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 5
238000009736 wetting Methods 0.000 claims description 5
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 4
229920001451 polypropylene glycol Polymers 0.000 claims description 4
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 claims description 2
OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims description 2
KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 claims description 2
230000000379 polymerizing effect Effects 0.000 claims description 2
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims 4
230000003472 neutralizing effect Effects 0.000 claims 4
239000011347 resin Substances 0.000 abstract description 44
229920005989 resin Polymers 0.000 abstract description 44
239000008199 coating composition Substances 0.000 abstract description 22
239000000126 substance Substances 0.000 description 17
239000011230 binding agent Substances 0.000 description 14
238000006116 polymerization reaction Methods 0.000 description 10
239000002245 particle Substances 0.000 description 8
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
239000012986 chain transfer agent Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
239000008367 deionised water Substances 0.000 description 4
238000007720 emulsion polymerization reaction Methods 0.000 description 4
239000003999 initiator Substances 0.000 description 4
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
206010034972 Photosensitivity reaction Diseases 0.000 description 3
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
238000006386 neutralization reaction Methods 0.000 description 3
230000036211 photosensitivity Effects 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
239000006184 cosolvent Substances 0.000 description 2
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000004408 titanium dioxide Substances 0.000 description 2
MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
239000004971 Cross linker Substances 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
102100028701 General vesicular transport factor p115 Human genes 0.000 description 1
101000767151 Homo sapiens General vesicular transport factor p115 Proteins 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
238000005273 aeration Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 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
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229910001870 ammonium persulfate Inorganic materials 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
230000015271 coagulation Effects 0.000 description 1
238000005345 coagulation Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000005336 cracking Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000002950 deficient Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000000945 filler Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
229910001869 inorganic persulfate Inorganic materials 0.000 description 1
239000004611 light stabiliser Substances 0.000 description 1
VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
UOMSUBPWUZCGQU-UHFFFAOYSA-N nonane-2-thiol Chemical compound CCCCCCCC(C)S UOMSUBPWUZCGQU-UHFFFAOYSA-N 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000005385 peroxodisulfate group Chemical group 0.000 description 1
125000004437 phosphorous atom Chemical group 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
230000010399 physical interaction Effects 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
238000012546 transfer Methods 0.000 description 1
SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-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
- 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
- C09D17/004—Pigment pastes, e.g. for mixing in paints containing an inorganic pigment
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/40—Introducing phosphorus atoms or phosphorus-containing groups
- 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
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/60—Particles characterised by their size
- C01P2004/61—Micrometer sized, i.e. from 1-100 micrometer
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/22—Rheological behaviour as dispersion, e.g. viscosity, sedimentation stability
- 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
- C09K23/14—Derivatives of phosphoric acid

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)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Inorganic Chemistry (AREA)
Pigments, Carbon Blacks, Or Wood Stains (AREA)
Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Paints Or Removers (AREA)

CA 2430991 2000-12-22 2001-11-19 Pigment dispersion and method of preparing the same Expired - Fee Related CA2430991C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US09/747,472		2000-12-22
US09/747,472 US6642338B2 (en)	2000-12-22	2000-12-22	Water-based acrylic emulsion dispersants utilized as grind resins for pigments and method of preparing the same
PCT/US2001/042956 WO2002051948A2 (en)	2000-12-22	2001-11-19	Pigment dispersion and method of preparing the same

Publications (2)

Publication Number	Publication Date
CA2430991A1 CA2430991A1 (en)	2002-07-04
CA2430991C true CA2430991C (en)	2008-08-05

Family

ID=25005195

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2430991 Expired - Fee Related CA2430991C (en)	2000-12-22	2001-11-19	Pigment dispersion and method of preparing the same

Country Status (9)

Country	Link
US (2)	US6642338B2 (de)
EP (1)	EP1366123B1 (de)
AT (1)	ATE334175T1 (de)
AU (1)	AU2002225601A1 (de)
CA (1)	CA2430991C (de)
DE (1)	DE60121824T2 (de)
ES (1)	ES2267859T3 (de)
MX (1)	MXPA03003284A (de)
WO (1)	WO2002051948A2 (de)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MY134362A (en) *	2002-11-20	2007-12-31	Efka Additives B V	Aqueous emulsion polymer as dipersant
DE102004010155A1 (de) *	2004-02-27	2005-09-15	Basf Ag	Verfahren zur Verbesserung der Lagerstabilität von Kompositpartikel-Dispersionen
DE102005038358A1 (de) *	2005-08-11	2007-02-15	Basf Ag	Verfahren zur Herstellung von Pigmentzubereitungen
DE102006062441A1 (de) *	2006-12-27	2008-07-03	Byk-Chemie Gmbh	Modifizierte Kammcopolymere
DE102007021870A1 (de) *	2007-05-10	2008-11-20	Clariant International Limited	Wässrige Pigmentpräparationen
DE102007021869A1 (de) *	2007-05-10	2008-11-13	Clariant International Limited	Anionische wasserlösliche Additive
DE102007021867A1 (de) *	2007-05-10	2008-11-20	Clariant International Limited	Pigmentpräparationen auf Wasserbasis
DE102007039783A1 (de) *	2007-08-23	2009-02-26	Clariant International Ltd.	Wässrige Pigmentpräparationen mit anionischen Additiven auf Allyl- und Vinyletherbasis
DE102008037973A1 (de) *	2008-08-16	2010-02-18	Clariant International Limited	Trockene Pigmentpräparationen mit anionischen Additiven
FR2939055A1 (fr) *	2008-12-03	2010-06-04	Coatex Sas	Utilisation de polymeres acryliques dont l'acide acrylique est issu du glycerol, comme agent de dispersion ou de broyage de matieres minerales.
US9034979B2 (en) *	2011-10-26	2015-05-19	Lubrizol Advanced Materials, Inc.	Dispersant composition
EP2771418B2 (de) *	2011-10-26	2021-12-29	Lubrizol Advanced Materials, Inc.	Dispersionszusammensetzung
GB2536155B (en) *	2012-04-05	2016-12-14	Fujifilm Imaging Colorants Ltd	Process, dispersion and ink
CN105283489B (zh)	2013-06-07	2019-02-12	巴斯夫欧洲公司	聚合物分散剂
CN104558431B (zh)	2013-10-28	2018-05-18	广东华润涂料有限公司	水性胶乳以及包含该水性胶乳的无机颜料颗粒的分散体
CN103626907A (zh) *	2013-11-15	2014-03-12	马钢(集团)控股有限公司	一种苯丙乳液、其合成方法及电工钢涂料
CN104073117A (zh) *	2014-06-23	2014-10-01	无锡市崇安区科技创业服务中心	一种水溶性丙烯酸树脂涂料及其制备方法
EP3535307B1 (de)	2016-11-04	2021-02-24	Basf Se	Neuartige monomere und polymere
GB201805083D0 (en) *	2018-03-28	2018-05-09	Croda Int Plc	Agrochemical polymer dispersants
CN109836534B (zh) *	2019-01-22	2020-12-04	苏州健雄职业技术学院	一种利用回流沉淀聚合制备温度响应性铁基纳米酶的方法
KR102370498B1 (ko)	2019-02-07	2022-03-07	최근윤	무기계 저점도 수성 접착코팅제 조성물 및 그 용도
KR102273484B1 (ko)	2019-11-28	2021-07-07	케이에스케미칼 주식회사	친환경 수계용 분산 조성물을 포함하는 안료 조성물

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3671502A (en)	1970-11-12	1972-06-20	Kendall & Co	Betaine copolymers with hydroxyalkylacrylates and hydroxyalkylmethacrylates
US4615813A (en)	1984-07-26	1986-10-07	The Lubrizol Corporation	Water-based metal-containing organic phosphate compositions
DE3603392A1 (de)	1986-02-05	1987-08-06	Basf Ag	Verfahren zur herstellung von polymerisaten der acrylsaeure oder methacrylsaeure
WO1988002381A1 (en)	1986-09-30	1988-04-07	E.I. Du Pont De Nemours And Company	Pigment dispersant resin with s-containing acid
NL8800068A (nl)	1988-01-12	1989-08-01	Stamicarbon	Hardbare dispersies.
US5266622A (en)	1988-05-05	1993-11-30	Bayer Aktiengesellschaft	Aqueous dispersions containing a synergistic dispersant combination
DE3815239A1 (de)	1988-05-05	1989-11-16	Bayer Ag	Waessrige dispersionen mit einer synergistischen dispergiermittelkombination
US4872916A (en) *	1988-09-22	1989-10-10	Sun Chemical Corporation	Phosphate ester pigment dispersant
BR9104402A (pt) *	1991-10-10	1993-04-20	Glasurit Do Brasil Limitada	Polimero de emulsao diluivel na agua,processo para a preparacao de um polimero de emulsao diluivel na agua,composicao de revestimento aquosa e emprego do polimero
DE4221381C1 (de)	1992-07-02	1994-02-10	Stockhausen Chem Fab Gmbh	Pfropf-Copolymerisate von ungesättigten Monomeren und Zuckern, Verfahren zu ihrer Herstellung und ihre Verwendung
DE4225922A1 (de)	1992-08-05	1994-02-10	Bayer Ag	Verwendung von Salzen mehrbasiger organischer Säuren mit mehrwertigen Kationen als Dispergiermittel für wäßrige Dispersionen und wäßriger Dispersionen, die derartige Dispergiermittel enthalten
AU659351B2 (en) *	1992-11-27	1995-05-11	Basf Corporation	Copolymer dispersant composition for inorganic pigments
US5389139A (en)	1994-02-14	1995-02-14	Basf Corporation	Nitro-substituted polymeric corrosion inhibitors for aluminum flake pigment
DE4421823A1 (de) *	1994-06-22	1996-01-04	Basf Lacke & Farben	Aus mindestens 3 Komponenten bestehendes Beschichtungsmittel, Verfahren zu seiner Herstellung sowie seine Verwendung
GB9418985D0 (en)	1994-09-21	1994-11-09	Albright & Wilson	Dispersion of solid particles in water
US5527614A (en)	1994-12-21	1996-06-18	Basf Corporation	Pigment dispersants with primary amine functionality suitable for use in cathodic electrocoat compositions
EP0755946A3 (de)	1995-07-24	1997-10-01	Basf Corp	Verfahren zur Herstellung von hydrophobierten Emulsionspolymeren, die so hergestellten Polymere und wässrige Anstrichzusammensetzungen aus diesen Polymeren
US5821283A (en)	1995-10-06	1998-10-13	Rohm And Haas Company	Ink composition and method for preparing
US6624241B2 (en) *	1999-05-21	2003-09-23	Basf Corporation	Waterborne coating compositions containing materials dispersed with water-soluble carbamate materials
US6346591B1 (en) *	1999-05-21	2002-02-12	Basf Corporation	Monomer and polymerization process
US6624279B2 (en) *	1999-05-21	2003-09-23	Basf Corporation	Water-soluble carbamate materials
US6410619B2 (en) *	1999-11-22	2002-06-25	Bayer Corporation	Method for conditioning organic pigments
DE10029803A1 (de) *	2000-06-16	2002-01-03	Basf Coatings Ag	Copolymerisate und Copolymerisatdispersionen, Verfahren zu ihrer Herstellung und ihre Verwendung
US6916877B2 (en) *	2000-06-16	2005-07-12	Basf Corporation	Coating composition including a water-based copolymer cross-linking with a water-dispersible cross-linking agent, method of preparing the same, and a cured film thereof

2000
- 2000-12-22 US US09/747,472 patent/US6642338B2/en not_active Expired - Fee Related
2001
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- 2001-11-19 CA CA 2430991 patent/CA2430991C/en not_active Expired - Fee Related
- 2001-11-19 DE DE60121824T patent/DE60121824T2/de not_active Expired - Lifetime
- 2001-11-19 EP EP01995101A patent/EP1366123B1/de not_active Expired - Lifetime
- 2001-11-19 WO PCT/US2001/042956 patent/WO2002051948A2/en not_active Ceased
- 2001-11-19 MX MXPA03003284A patent/MXPA03003284A/es unknown
- 2001-11-19 ES ES01995101T patent/ES2267859T3/es not_active Expired - Lifetime
- 2001-11-19 AU AU2002225601A patent/AU2002225601A1/en not_active Abandoned
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US6642338B2 (en)	2003-11-04
ATE334175T1 (de)	2006-08-15
WO2002051948A3 (en)	2003-08-21
MXPA03003284A (es)	2003-08-07
US20040048959A1 (en)	2004-03-11
DE60121824D1 (de)	2006-09-07
CA2430991A1 (en)	2002-07-04
EP1366123B1 (de)	2006-07-26
US6777519B2 (en)	2004-08-17
US20020132890A1 (en)	2002-09-19
EP1366123A2 (de)	2003-12-03
DE60121824T2 (de)	2007-08-09
ES2267859T3 (es)	2007-03-16
AU2002225601A1 (en)	2002-07-08
WO2002051948A2 (en)	2002-07-04

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Publication	Publication Date	Title
CA2430991C (en)	2008-08-05	Pigment dispersion and method of preparing the same
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NL8503327A (nl)	1986-07-01	In water oplosbaar dispergeermiddel voor pigmentmaterialen op waterbasis.
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JPH0678497B2 (ja)	1994-10-05	水性塗料組成物
WO2001064764A1 (en)	2001-09-07	Resin-fortified emulsion polymers for water-borne inks and the method for preparing the same
CA2430985C (en)	2007-11-13	Pigment dispersion and method of preparing the same
KR0150625B1 (ko)	1998-10-15	도로표지용 수용성 아크릴계수지 및 그 제조방법
US5639813A (en)	1997-06-17	Coating compositions containing ethylene-acrylic acid copolymers with polyamide grafts as rheology modifiers
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WO2014169414A1 (en)	2014-10-23	Polymer particles adsorbed to sulfate-process titanium dioxide
EP0495000A4 (en)	1992-10-21	Stable emulsion polymers and methods of preparing same
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JP3635159B2 (ja)	2005-04-06	有機色素−親水性樹脂複合体
AU767612B2 (en)	2003-11-20	Aqueous polymer dispersion
JPH0674310B2 (ja)	1994-09-21	樹脂水性分散体の製造方法
JPS6038428B2 (ja)	1985-08-31	水性被覆用組成物
HK1007317A1 (en)	1999-04-09	Addition polymer particles