CA2535818A1 - Copolymer surfactants - Google Patents
Copolymer surfactants Download PDFInfo
- Publication number
- CA2535818A1 CA2535818A1 CA002535818A CA2535818A CA2535818A1 CA 2535818 A1 CA2535818 A1 CA 2535818A1 CA 002535818 A CA002535818 A CA 002535818A CA 2535818 A CA2535818 A CA 2535818A CA 2535818 A1 CA2535818 A1 CA 2535818A1
- Authority
- CA
- Canada
- Prior art keywords
- paint
- mixture
- surfactant
- copolymer
- shear viscosity
- 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.)
- Granted
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- 229920001577 copolymer Polymers 0.000 title claims abstract 28
- 239000004094 surface-active agent Substances 0.000 title claims abstract 28
- 239000003973 paint Substances 0.000 claims abstract 58
- 239000000203 mixture Substances 0.000 claims abstract 43
- 238000000034 method Methods 0.000 claims abstract 18
- 239000003086 colorant Substances 0.000 claims abstract 17
- 239000000049 pigment Substances 0.000 claims abstract 8
- 239000002904 solvent Substances 0.000 claims abstract 7
- 239000004816 latex Substances 0.000 claims abstract 3
- 229920000126 latex Polymers 0.000 claims abstract 3
- 239000000178 monomer Substances 0.000 claims 24
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 13
- 239000002585 base Substances 0.000 claims 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 8
- -1 brown iron oxide Inorganic materials 0.000 claims 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims 5
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims 4
- 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 4
- 229920002125 Sokalan® Polymers 0.000 claims 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical group O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims 4
- 239000003513 alkali Substances 0.000 claims 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 4
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims 4
- 239000001023 inorganic pigment Substances 0.000 claims 4
- 239000012860 organic pigment Substances 0.000 claims 4
- 239000004584 polyacrylic acid Substances 0.000 claims 4
- 239000002562 thickening agent Substances 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- 229920003169 water-soluble polymer Polymers 0.000 claims 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 3
- 239000003995 emulsifying agent Substances 0.000 claims 3
- 239000000839 emulsion Substances 0.000 claims 3
- IAFBRPFISOTXSO-UHFFFAOYSA-N 2-[[2-chloro-4-[3-chloro-4-[[1-(2,4-dimethylanilino)-1,3-dioxobutan-2-yl]diazenyl]phenyl]phenyl]diazenyl]-n-(2,4-dimethylphenyl)-3-oxobutanamide Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)C(C(=O)C)N=NC(C(=C1)Cl)=CC=C1C(C=C1Cl)=CC=C1N=NC(C(C)=O)C(=O)NC1=CC=C(C)C=C1C IAFBRPFISOTXSO-UHFFFAOYSA-N 0.000 claims 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims 2
- 239000004908 Emulsion polymer Substances 0.000 claims 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 2
- 229920002845 Poly(methacrylic acid) Polymers 0.000 claims 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000002280 amphoteric surfactant Substances 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 239000003945 anionic surfactant Substances 0.000 claims 2
- 229920001400 block copolymer Polymers 0.000 claims 2
- 229940067573 brown iron oxide Drugs 0.000 claims 2
- 239000006229 carbon black Substances 0.000 claims 2
- 239000001913 cellulose Substances 0.000 claims 2
- 229920002678 cellulose Polymers 0.000 claims 2
- 238000007334 copolymerization reaction Methods 0.000 claims 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical group [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 claims 2
- PBJZAYSKNIIHMZ-UHFFFAOYSA-N ethyl carbamate;oxirane Chemical class C1CO1.CCOC(N)=O PBJZAYSKNIIHMZ-UHFFFAOYSA-N 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims 2
- WTFXARWRTYJXII-UHFFFAOYSA-N iron(2+);iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+2].[Fe+3].[Fe+3] WTFXARWRTYJXII-UHFFFAOYSA-N 0.000 claims 2
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 claims 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims 2
- 239000006233 lamp black Substances 0.000 claims 2
- 239000002736 nonionic surfactant Substances 0.000 claims 2
- 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 2
- 229920002401 polyacrylamide Polymers 0.000 claims 2
- 229920000570 polyether Polymers 0.000 claims 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims 2
- 239000004408 titanium dioxide Substances 0.000 claims 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims 1
- 239000004641 Diallyl-phthalate Substances 0.000 claims 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical group CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000012874 anionic emulsifier Substances 0.000 claims 1
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- 230000002209 hydrophobic effect Effects 0.000 claims 1
- 238000004890 malting Methods 0.000 claims 1
- 125000005395 methacrylic acid group Chemical group 0.000 claims 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims 1
- 239000012875 nonionic emulsifier Substances 0.000 claims 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract 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
- C09D17/001—Pigment pastes, e.g. for mixing in paints in aqueous medium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/0004—Preparation of sols
- B01J13/0034—Additives, e.g. in view of promoting stabilisation or peptisation
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/34—Higher-molecular-weight carboxylic acid esters
Abstract
The present invention relates to copolymer surfactants and their use in, e.g ., coatings such as latex paint and solvent-based paint, and to a method of dispersing colored pigments using the copolymer surfactant, colorant compositions in which at least one pigment is dispersed by a copolymer surfactant of the invention, a paint which has a colorant composition of the invention, and a method for making a paint having a colorant composition of the invention.
Claims (57)
1. A copolymer surfactant chain comprising at least one of hydrophobic monomer and a plurality of hydrophilic monomers.
2. A copolymer surfactant comprising:
(a) from about 10% to about 80% by weight of at least one C3-C12 .alpha.,.beta.-ethylenically unsaturated carboxylic acid or anhydride;
(b) from about 10% to about 80% by weight of at least one C2-C12, .alpha.,.beta.-ethylenically unsaturated vinyl monomer;
(c) from about 0.01% to about 20% by weight of at least one surfactant monomer; and (d) optionally, up to about 5% by weight of an ethylenically unsaturated cross-linking monomer.
(a) from about 10% to about 80% by weight of at least one C3-C12 .alpha.,.beta.-ethylenically unsaturated carboxylic acid or anhydride;
(b) from about 10% to about 80% by weight of at least one C2-C12, .alpha.,.beta.-ethylenically unsaturated vinyl monomer;
(c) from about 0.01% to about 20% by weight of at least one surfactant monomer; and (d) optionally, up to about 5% by weight of an ethylenically unsaturated cross-linking monomer.
3. The copolymer surfactant of claim 2, wherein the at least one C3-C12 .alpha.,.beta.-ethylenically unsaturated carboxylic acid or anhydride is methacrylic acid, acrylic acid, itaconic acid, or a mixture thereof.
4. The copolymer surfactant of claim 2, wherein the at least one C3-C12, .alpha.,.beta.-ethylenically unsaturated vinyl monomer is selected from ethyl acrylate, ethyl methacrylate, butyl acrylate, methyl methacrylate, vinyl acetate, acrylonitrile, or a mixture thereof.
5. The copolymer surfactant of claim 4, wherein one C2-C12, .alpha.,.beta.-ethylenically unsaturated vinyl monomer is vinyl acetate and at least one other C2-C12, .alpha.,.beta.-ethylenically unsaturated vinyl monomer is ethyl methacrylate, butyl acrylate, methyl methacrylate, or a mixture thereof.
6. The copolymer surfactant of claim 5, wherein the C2-C12, .alpha.,.beta.-ethylenically unsaturated vinyl monomers are butyl acrylate and vinyl acetate.
7. The copolymer surfactant of claim 5, wherein the C2-C12, .alpha.,.beta.-ethylenically unsaturated vinyl monomers are ethyl methacrylate, butyl acrylate and vinyl acetate.
8. The copolymer surfactant of claim 2, wherein the surfactant monomer is a tristyrylphenylpoly(ethyleneoxy) (meth)acrylate, an alkylpolyethyleneoxy (meth)acrylate,.an allcylphenylpolyethyleneoxy (meth)acrylate, or a mixture thereof, wherein each alkyl group contains, independently, from 1 to 30 carbon atoms.
9. The copolymer surfactant of claim 8, wherein the surfactant monomer is nonylpoly(ethyleneoxy) acrylate, decylpoly(ethyleneoxy) acrylate, undecylpoly(ethyleneoxy) acrylate, oleylpoly(ethyleneoxy) methacrylate, behenylpoly(ethyleneoxy) methacrylate, tristyrylphenylpoly(ethyleneoxy) methacrylate, or a mixture thereof.
10. A method of making the copolymer surfactant of claim 2 by solution copolymerization in a solvent, wherein the solvent is ethylene glycol, propylene glycol, glycerol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol with a number average molecular weight below about 1,000 Daltons, or a mixture thereof.
11. A method of making the copolymer surfactant of claim 2 by emulsion copolymerization using an emulsifier, wherein the emulsifier is at least one anionic emulsifier, at least one nonionic emulsifier, or a mixture thereof.
12. The method of claim 11, wherein the emulsifier comprises a sulfonate, a sulfate, an alkylphenol ethoxylate, or a mixture thereof.
13. A copolymer surfactant consisting essentially of:
(a) from about 20% to about 45% by weight of methacrylic acid;
(b) from about 50% to about 75% by weight of a plurality of C2-C12, .alpha.,.beta.-ethylenically unsaturated vinyl monomers, wherein one C2-C12, .alpha.,.beta.-ethylenically unsaturated vinyl monomer is vinyl acetate and at least one other C2-C12, .alpha.,.beta.-ethylenically unsaturated vinyl monomer is ethyl methacrylate, butyl acrylate, methyl methacrylate, or a mixture thereof;
(c) from about 0.5% to about 13% by weight of a surfactant monomer selected from nonylpoly(ethyleneoxy) acrylate, decylpoly(ethyleneoxy) acrylate, undecylpoly(ethyleneoxy) acrylate, oleylpoly(ethyleneoxy) methacrylate, behenylpoly(ethyleneoxy) methacrylate, tristyrylphenylpoly(ethyleneoxy) methacryIate, or a mixture thereof;
(d) optionally, up to about 1% by weight of diallyl phthalate or ethylene glycol diacrylate.
(a) from about 20% to about 45% by weight of methacrylic acid;
(b) from about 50% to about 75% by weight of a plurality of C2-C12, .alpha.,.beta.-ethylenically unsaturated vinyl monomers, wherein one C2-C12, .alpha.,.beta.-ethylenically unsaturated vinyl monomer is vinyl acetate and at least one other C2-C12, .alpha.,.beta.-ethylenically unsaturated vinyl monomer is ethyl methacrylate, butyl acrylate, methyl methacrylate, or a mixture thereof;
(c) from about 0.5% to about 13% by weight of a surfactant monomer selected from nonylpoly(ethyleneoxy) acrylate, decylpoly(ethyleneoxy) acrylate, undecylpoly(ethyleneoxy) acrylate, oleylpoly(ethyleneoxy) methacrylate, behenylpoly(ethyleneoxy) methacrylate, tristyrylphenylpoly(ethyleneoxy) methacryIate, or a mixture thereof;
(d) optionally, up to about 1% by weight of diallyl phthalate or ethylene glycol diacrylate.
14. A colorant composition comprising the copolymer surfactant of claim 1, water and at least one pigment.
15. The colorant composition of claim 14, which further comprises at least one oxygenated solvent.
16. A colorant composition comprising the copolymer surfactant of claim 2, water and at least one pigment.
17. The colorant composition of claim 16, which further comprises at least one oxygenated solvent.
18. A method of malting a colorant composition comprising admixing the copolymer surfactant of claim 1, water and at least one pigment, wherein the pigment is an organic pigment, an inorganic pigment, or a mixture thereof.
19. The method of claim 18, wherein the colorant composition further comprises at least one conventional surfactant.
20. The method of claim 19, wherein the conventional surfactant is an anionic surfactant, a nonionic surfactant, an amphoteric surfactant, or a mixture thereof.
21. The method of claim 18, wherein the colorant composition further comprises a water-soluble polymer selected from a polycarboxylic acid, a copolymer comprising a monomer containing a carboxylic acid, an alkali soluble emulsion polymer, a cellulose derivative, a salt of a polyacrylic acid, a salt of a copolymer comprising a monomer containing an acrylic acid, polyvinylpyrrolidone, a copolymer comprising vinylpyrrolidone monomer, or a mixture thereof.
22. The method of claim 21, wherein the water-soluble polymer is a salt of a polyacrylic acid, a salt of a copolymer comprising a monomer containing an acrylic acid, or a mixture thereof.
23. The method of claim 18, wherein the inorganic pigment is titanium dioxide white, carbon black, lampblack, black iron oxide, yellow iron oxide, brown iron oxide, red iron oxide, or a mixture thereof.
24. The method of claim 18, wherein the organic pigment is phthalocyanine blue, phthalocyanine green, monoarylide yellow, diarylide yellow, berzimidazolone yellow, heterocyclic yellow, BAN orange, quinacridone magenta, quinacridone violet, organic red, or a mixture thereof.
25. The method of claim 24, wherein the organic red is a metallized azo red, a nonmetallized azo red, or a mixture thereof.
26. A method of making a colorant composition comprising admixing the copolymer surfactant of claim 2, water and at least one pigment, wherein the pigment is an organic pigment, an inorganic pigment, or a mixture thereof.
27. The method of claim 26, wherein the colorant composition further comprises at least one conventional surfactant.
28. The method of claim 27, wherein the conventional surfactant is an anionic surfactant, a nonionic surfactant, an amphoteric surfactant, or a mixture thereof.
29. The method of claim 26, wherein the colorant composition further comprises a water-soluble polymer selected from a polycarboxylic acid, a copolymer comprising a monomer containing a carboxylic acid, an alkali soluble emulsion polymer, a cellulose derivative, a salt of a polyacrylic acid, a salt of a copolymer comprising a monomer containing an acrylic acid, polyvinylpyrrolidone, a copolymer comprising vinylpyrrolidone monomer, or a mixture thereof.
30. The method of claim 29, wherein the water-soluble polymer is a salt of a polyacrylic acid, a salt of a copolymer comprising a monomer containing an acrylic acid, or a mixture thereof.
31. The method of claim 26, wherein the inorganic pigment is titanium dioxide white, carbon black, lampblack, black iron oxide, yellow iron oxide, brown iron oxide, red iron oxide, or a mixture thereof.
32. The method of claim 26, wherein the organic pigment is phthalocyanine blue, phthalocyanine green, monoarylide yellow, diarylide yellow, benzimidazolone yellow, heterocyclic yellow, DAN orange, quinacridone magenta, quinacridone violet, organic red, or a mixture thereof.
33. The method of claim 32, wherein the organic red is a metallized azo red, a nonmetallized azo red, or a mixture thereof.
34. A paint comprising the colorant composition of claim 14 and a tint-base.
35. The paint of claim 34, wherein the paint does not substantially change color after rub-up.
36. The paint of claim 34, wherein the paint is a solvent-based paint.
37. The paint of claim 34, wherein the paint is a latex paint.
38. The paint of claim 37, wherein the paint further comprises at least one associative thickener.
39. The paint of claim 38, wherein the associative thickener is a nonionic hydrophobically modified ethylene oxide urethane block copolymer, a hydrophobically-modified polyether, a hydrophobically-modified alkali soluble emulsion, a hydrophobically-modified poly(meth)acrylic acid, a hydrophobically-modified hydroxyethyl cellulose, a hydrophobically-modified poly(acrylamide), or a mixture thereof.
40. The paint of claim 37, wherein the Stormer low-shear viscosity of the paint is within about ~ 10% of the Stormer low-shear viscosity of the tint-base from which the paint was formed.
41. The paint of claim 37, wherein the Stormer low-shear viscosity of the paint is within about ~ 5% of the Stormer low-shear viscosity of the tint-base from which the paint was formed.
42. The paint of claim 37, wherein the Stormer low-shear viscosity of the paint is within about ~ 3% of the Stormer low-shear viscosity of the tint-base from which the paint was formed.
43. The paint of claim 37, wherein the ICI high-shear viscosity of the paint is within about ~ 10% of the ICI high-shear viscosity of the tint-base from which the paint was formed.
44. The paint of claim 37, wherein the flow/level rating of the paint, measured at 25°C according to ASTM Standard D4062-99, is about 10.
45. A paint comprising the colorant composition of claim 16 and a tint-base.
46. The paint of claim 45, wherein the paint does not substantially change color after rub-up.
47. The paint of claim 45, wherein the paint is a solvent-based paint.
48. The paint of claim 45, wherein the paint is a latex paint.
49. The paint of claim 48, wherein the paint further comprises at least one associative thickener.
50. The paint of claim 49, wherein the associative thickener is a nonionic hydrophobically modified ethylene oxide urethane block copolymer, a hydrophobically-modified polyether, a hydrophobically-modified alkali soluble emulsion, a hydrophobically-modified poly(meth)acrylic acid, a hydrophobically-modified hydroxyethyl cellulose, a hydrophobically-modified poly(acrylamide), or a mixture thereof.
51. The paint of claim 48, wherein the Stormer low-shear viscosity of the paint is within about ~ 10% of the Stormer low-shear viscosity of the tint-base from which the paint was formed.
52. The paint of claim 48, wherein the Stormer low-shear viscosity of the paint is within about ~ 5% of the Stormer low-shear viscosity of the tint-base from which the paint was formed.
53. The paint of claim 48, wherein the Stormer low-shear viscosity of the paint is within about ~ 3% of the Stormer low-shear viscosity of the tint-base from which the paint was formed.
54. The paint of claim 48, wherein the ICI high-shear viscosity of the paint is within about ~ 10% of the ICI high-shear viscosity of the tint-base from which the paint was formed.
55. The paint of claim 48, wherein the flow/level rating of the paint, measured at 25°C according to ASTM Standard D4062-99, is about 10.
56. A method of making a paint comprising admixing a tint-base and the colorant composition of claim 14.
57. A method of making a paint comprising admixing a tint-base and the colorant composition of claim 16.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49636603P | 2003-08-18 | 2003-08-18 | |
| US60/496,366 | 2003-08-18 | ||
| US10/728,599 US7402627B2 (en) | 2003-08-18 | 2003-12-04 | Precursor colorant composition for latex paint |
| US10/728,599 | 2003-12-04 | ||
| PCT/US2004/026216 WO2005019353A2 (en) | 2003-08-18 | 2004-08-13 | Copolymer surfactants |
Publications (2)
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| CA2535818A1 true CA2535818A1 (en) | 2005-03-03 |
| CA2535818C CA2535818C (en) | 2011-04-05 |
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| CA2535818A Active CA2535818C (en) | 2003-08-18 | 2004-08-13 | Copolymer surfactants |
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| EP (1) | EP1660597B1 (en) |
| CA (1) | CA2535818C (en) |
| DK (1) | DK1660597T3 (en) |
| ES (1) | ES2455315T3 (en) |
| PL (1) | PL1660597T3 (en) |
| RU (1) | RU2412966C2 (en) |
| WO (1) | WO2005019353A2 (en) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9139676B2 (en) * | 2003-08-18 | 2015-09-22 | Benjamin Moore & Co. | Environmentally friendly colorant compositions and latex paints/coatings |
| US7402627B2 (en) * | 2003-08-18 | 2008-07-22 | Columbia Insurance Company | Precursor colorant composition for latex paint |
| US20090076211A1 (en) * | 2003-08-18 | 2009-03-19 | Yong Yang | Copolymer surfactants |
| US8329807B2 (en) * | 2003-08-18 | 2012-12-11 | Columbia Insurance Company | Latex paint film resistant to adverse effects of water, and compositions and methods for making same |
| CN1946815B (en) * | 2004-01-08 | 2015-06-17 | 赫尔克里士公司 | Colorant compatible synthetic thickener for paint |
| EP1584371A1 (en) * | 2004-04-07 | 2005-10-12 | Urea Casale S.A. | Fluid bed granulation process and apparatus |
| US7482395B2 (en) * | 2005-01-24 | 2009-01-27 | No-Burn Investments, L.L.C. | Intumescent fire retardant latex paint with mold inhibitor |
| BRPI0608547A2 (en) * | 2005-03-18 | 2010-11-16 | Valspar Sourcing Inc | coloring composition, universal coloring system, and paint or coating |
| US8846154B2 (en) | 2005-06-07 | 2014-09-30 | S.C. Johnson & Son, Inc. | Carpet décor and setting solution compositions |
| DE102005042039A1 (en) * | 2005-09-02 | 2007-03-08 | Basf Ag | Aqueous polyvinyl acetate dispersions with high shear stability |
| WO2009046131A1 (en) * | 2007-10-01 | 2009-04-09 | Elementis Specialties, Inc. | A method to improve the color acceptance of viscosity stabilized latex paints |
| US7906577B2 (en) * | 2008-01-18 | 2011-03-15 | Rhodia Operations | Latex binders, aqueous coatings and paints having freeze-thaw stability and methods for using same |
| AU2013200757B2 (en) * | 2008-01-18 | 2014-06-26 | Rhodia Operations | Latex binders, aqueous coatings and paints having freeze-thaw stability and methods for using same |
| FR2928930B1 (en) * | 2008-03-18 | 2011-11-18 | Coatex Sas | PROCESS FOR THE DISPERSION IN WATER OF ALKYD RESINS WITH ASSOCIATIVE POLYMERS, FORMULATIONS OBTAINED AND AQUEOUS PAINTS CONTAINING SAME. |
| DK2519591T3 (en) * | 2009-12-29 | 2014-04-28 | Sawgrass Europ S A | Ink with altered rheology and printing method |
| ES2646778T3 (en) * | 2012-02-10 | 2017-12-15 | Arkema, Inc. | Latex binders useful in coating compositions with low VOC content or zero content |
| CN104284914A (en) * | 2012-04-24 | 2015-01-14 | 塞拉尼斯乳液有限公司 | Vinyl ester-based copolymer dispersions from a continuous tubular emulsion polymerization process |
| EP2877506B1 (en) | 2012-09-17 | 2019-02-27 | Rohm and Haas Company | A multi-stage polymer as a grinding additive and preparation process thereof |
| WO2014124123A1 (en) * | 2013-02-06 | 2014-08-14 | Encell Technology, Inc. | Nickel iron battery employing untreated polyolefin separator with a surfactant in the electrolyte |
| CN103421389B (en) * | 2013-08-06 | 2014-12-10 | 江苏科技大学 | Water-based environment-friendly opaque medium-yellow color paste and preparation method thereof |
| GB201405624D0 (en) | 2014-03-28 | 2014-05-14 | Synthomer Uk Ltd | Method of making a branched polymer, a branched polymer and uses of such a polymer |
| RU2587091C1 (en) * | 2014-12-30 | 2016-06-10 | Общество с ограниченной ответственностью "НАУЧНО-ПРОИЗВОДСТВЕННАЯ ФИРМА "РЕКОН" | Method of producing aqueous epoxy emulsion |
| KR20180077252A (en) * | 2015-10-30 | 2018-07-06 | 클라리언트 인터내셔널 리미티드 | Metal dispersions having increased stability |
| US20180327624A1 (en) * | 2015-11-25 | 2018-11-15 | Rohm And Haas Company | Acid destabilization of elastomeric roof coating |
| US20210348003A1 (en) * | 2018-03-28 | 2021-11-11 | Basf Coatings Gmbh | Aqueous basecoat and production of multi-coat paint systems using the basecoat |
| CN109722062A (en) * | 2018-12-21 | 2019-05-07 | 英德科迪颜料技术有限公司 | A kind of preparation method of core-shell structure transparent ferric oxide coated pigment |
| CN110280182B (en) * | 2019-06-21 | 2021-09-24 | 中科广化（重庆）新材料研究院有限公司 | Application of sulfur/phosphorus hybrid polyether modified polycarboxylic acid |
| US11345769B2 (en) | 2019-12-30 | 2022-05-31 | Columbia Insurance Company | Hydrophobic, low glass transition temperature oligomer with high level of chain transfer agent |
| CN113230987A (en) * | 2021-05-24 | 2021-08-10 | 南京工业大学 | Simple preparation method of magnetic chitosan aerogel |
| CN115073869A (en) * | 2021-08-12 | 2022-09-20 | 东莞市集丰塑化材料有限公司 | Preparation method of acrylic solid pigment and acrylic solid pigment |
| WO2024006141A1 (en) | 2022-06-30 | 2024-01-04 | Benjamin Moore & Co. | Hydrophobic, low glass transition temperature oligomer with chain transfer agent |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1616074A (en) * | 1925-10-31 | 1927-02-01 | Mh Treadwell Co | Hot-metal container |
| US3769247A (en) * | 1972-04-10 | 1973-10-30 | Dow Chemical Co | Cellulose ether thickener for latex paint |
| US4138381A (en) * | 1975-04-14 | 1979-02-06 | E. I. Du Pont De Nemours And Company | Polymeric thickeners, processes for their preparation and uses thereof |
| US4243430A (en) | 1977-09-21 | 1981-01-06 | Rohm And Haas Company | Pigment dispersant for aqueous paints |
| AU527072B2 (en) | 1978-11-27 | 1983-02-17 | Dow Chemical Company, The | Aqueous emulsion copolymer |
| US4384096A (en) * | 1979-08-27 | 1983-05-17 | The Dow Chemical Company | Liquid emulsion polymers useful as pH responsive thickeners for aqueous systems |
| US4348294A (en) * | 1980-06-26 | 1982-09-07 | Occidental Chemical Corporation | One package replenisher for aluminum cleaner |
| US4432881A (en) * | 1981-02-06 | 1984-02-21 | The Dow Chemical Company | Water-dispersible hydrophobic thickening agent |
| US4529773A (en) * | 1982-03-17 | 1985-07-16 | David Witiak | Alkali-soluble emulsion polymers in acidic surfactant compositions |
| US4423199A (en) * | 1982-09-30 | 1983-12-27 | Rohm And Haas Company | Acrylamide containing emulsion copolymers for thickening purposes |
| US4421902A (en) * | 1982-09-30 | 1983-12-20 | Rohm And Haas Company | Alkyl, poly(oxyethylene) poly(carbonyloxyethylene) acrylate emulsion copolymers for thickening purposes |
| DE3311752A1 (en) * | 1983-03-31 | 1984-10-04 | Hoechst Ag, 6230 Frankfurt | COPOLYMERISATE CONTAINING CROTONESTERS, METHOD FOR THE PRODUCTION THEREOF, AND THEIR USE AS A THICKENER IN AQUEOUS SYSTEMS AND AS A SIZING AGENT |
| US4892916A (en) * | 1984-08-15 | 1990-01-09 | Allied Colloids Limited | Polymeric thickeners and their production |
| US4600761A (en) * | 1985-04-04 | 1986-07-15 | Alco Chemical Corporation | Acrylic emulsion copolymers for thickening aqueous systems and copolymerizable surfactant monomers for use therein |
| US4616074A (en) * | 1985-10-01 | 1986-10-07 | Alco Chemical Corporation | Acrylic-methylene succinic ester emulsion copolymers for thickening aqueous systems |
| US5874495A (en) * | 1994-10-03 | 1999-02-23 | Rhodia Inc. | Polymers useful as PH responsive thickeners and monomers therefor |
| US5527614A (en) * | 1994-12-21 | 1996-06-18 | Basf Corporation | Pigment dispersants with primary amine functionality suitable for use in cathodic electrocoat compositions |
| US6057384A (en) * | 1997-10-31 | 2000-05-02 | Hewlett-Packard Company | Latex polymer blends for improving the permanence of ink-jet inks |
| ES2297929T3 (en) * | 1998-07-10 | 2008-05-01 | Basf Corporation | CONTINUOUS MASS POLYMERIZATION AND STERIFICATION AND COMPOSITION PROCEDURES INCLUDING THE POLYMER PRODUCT0. |
| US6762269B1 (en) * | 1998-08-13 | 2004-07-13 | National Starch And Chemical Investment Holding Corporation | High temperature viscosity stable thickener |
| US6337366B1 (en) * | 1999-03-25 | 2002-01-08 | Rohm And Haas | Method of improving viscosity stability of aqueous compositions |
| MXPA01001665A (en) * | 2000-02-18 | 2002-04-01 | John Michael Friel | PAINTINGS FOR THE MARKING OF ROADS, PREPARED FROM PREPINTURES; METHOD AND APPARATUS FOR FORMING ZONES AND LINES MARKED ON THE ROADS, WITH SUCH PAINTS AND DEVICE FOR APPLYING SUCH PAINTS |
| US20040151886A1 (en) * | 2000-03-06 | 2004-08-05 | Bobsein Barrett Richard | Binder composition |
| US6602948B2 (en) * | 2000-06-20 | 2003-08-05 | Jerome M. Harris | Method of reducing syneresis in aqueous compositions |
| US6887928B2 (en) * | 2001-02-28 | 2005-05-03 | Rohm And Haas Company | Method of improving viscosity stability upon addition of a colorant component |
| AU784842B2 (en) * | 2001-02-28 | 2006-07-06 | Rohm And Haas Company | Method of improving viscosity stability upon addition of a colorant component |
| US6812278B2 (en) * | 2001-02-28 | 2004-11-02 | Rohm And Haas Company | Method of improving viscosity stability upon addition of an aqueous tinting composition |
| US7189767B2 (en) | 2001-03-30 | 2007-03-13 | Rohm And Haas Company | Colorants, dispersants, dispersions, and inks |
| US20030055135A1 (en) | 2001-09-17 | 2003-03-20 | Westvaco Corporation | Pigmented ink jet inks |
| DE60324225D1 (en) | 2002-06-14 | 2008-12-04 | Rohm & Haas | Colorants, dispersants and dispersions containing polymeric nanoparticles |
| US7402627B2 (en) | 2003-08-18 | 2008-07-22 | Columbia Insurance Company | Precursor colorant composition for latex paint |
-
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- 2003-12-04 US US10/728,599 patent/US7402627B2/en not_active Expired - Lifetime
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2004
- 2004-08-13 PL PL04780973T patent/PL1660597T3/en unknown
- 2004-08-13 WO PCT/US2004/026216 patent/WO2005019353A2/en active Application Filing
- 2004-08-13 DK DK04780973.6T patent/DK1660597T3/en active
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- 2004-08-13 RU RU2006108539/05A patent/RU2412966C2/en active
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2005019353A2 (en) | 2005-03-03 |
| US7402627B2 (en) | 2008-07-22 |
| WO2005019353A3 (en) | 2005-11-03 |
| EP1660597A4 (en) | 2007-06-06 |
| DK1660597T3 (en) | 2014-04-22 |
| PL1660597T3 (en) | 2014-07-31 |
| CA2535818C (en) | 2011-04-05 |
| US20050039635A1 (en) | 2005-02-24 |
| US20060167172A1 (en) | 2006-07-27 |
| US7750074B2 (en) | 2010-07-06 |
| RU2412966C2 (en) | 2011-02-27 |
| EP1660597B1 (en) | 2014-03-05 |
| EP1660597A2 (en) | 2006-05-31 |
| RU2006108539A (en) | 2007-09-27 |
| ES2455315T3 (en) | 2014-04-15 |
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