CA2866651C - Viscosity suppression of associative thickeners using organophosphates - Google Patents
Viscosity suppression of associative thickeners using organophosphates Download PDFInfo
- Publication number
- CA2866651C CA2866651C CA2866651A CA2866651A CA2866651C CA 2866651 C CA2866651 C CA 2866651C CA 2866651 A CA2866651 A CA 2866651A CA 2866651 A CA2866651 A CA 2866651A CA 2866651 C CA2866651 C CA 2866651C
- Authority
- CA
- Canada
- Prior art keywords
- associative thickener
- thickener composition
- hydrophobic group
- alkyl
- hydrophobically modified
- 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.)
- Active
Links
- 239000002562 thickening agent Substances 0.000 title claims abstract description 40
- 230000001629 suppression Effects 0.000 title description 3
- 125000001165 hydrophobic group Chemical group 0.000 claims abstract description 31
- 229920000642 polymer Polymers 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 229920000570 polyether Polymers 0.000 claims description 14
- 230000002209 hydrophobic effect Effects 0.000 claims description 13
- -1 ethylhexyl Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229920003180 amino resin Polymers 0.000 claims description 7
- PBJZAYSKNIIHMZ-UHFFFAOYSA-N ethyl carbamate;oxirane Chemical class C1CO1.CCOC(N)=O PBJZAYSKNIIHMZ-UHFFFAOYSA-N 0.000 claims description 7
- 229920000058 polyacrylate Polymers 0.000 claims description 5
- 229920001400 block copolymer Polymers 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 150000004676 glycans Chemical class 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 229920000193 polymethacrylate Polymers 0.000 claims description 3
- 229920001282 polysaccharide Polymers 0.000 claims description 3
- 239000005017 polysaccharide Substances 0.000 claims description 3
- 229930182556 Polyacetal Natural products 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 229920006324 polyoxymethylene Polymers 0.000 claims description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 239000000243 solution Substances 0.000 description 35
- 239000012855 volatile organic compound Substances 0.000 description 22
- 238000000576 coating method Methods 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 10
- 229910019142 PO4 Inorganic materials 0.000 description 8
- 239000004721 Polyphenylene oxide Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000010452 phosphate Substances 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
- 229920000858 Cyclodextrin Polymers 0.000 description 5
- 229940097362 cyclodextrins Drugs 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical group 0.000 description 4
- 239000012736 aqueous medium Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 229920001059 synthetic polymer Polymers 0.000 description 4
- 229940087291 tridecyl alcohol Drugs 0.000 description 4
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000033228 biological regulation Effects 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- LJKDOMVGKKPJBH-UHFFFAOYSA-N 2-ethylhexyl dihydrogen phosphate Chemical compound CCCCC(CC)COP(O)(O)=O LJKDOMVGKKPJBH-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- 238000012384 transportation and delivery Methods 0.000 description 2
- 229920003169 water-soluble polymer Polymers 0.000 description 2
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- YCUKMYFJDGKQFC-UHFFFAOYSA-N 2-(octan-3-yloxymethyl)oxirane Chemical compound CCCCCC(CC)OCC1CO1 YCUKMYFJDGKQFC-UHFFFAOYSA-N 0.000 description 1
- RQINQJTUMGQYOB-UHFFFAOYSA-N 6-methylheptyl dihydrogen phosphate Chemical compound CC(C)CCCCCOP(O)(O)=O RQINQJTUMGQYOB-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004710 electron pair approximation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 125000001046 glycoluril group Chemical group [H]C12N(*)C(=O)N(*)C1([H])N(*)C(=O)N2* 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229920013746 hydrophilic polyethylene oxide Polymers 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
-
- 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
-
- 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
- C09D7/43—Thickening agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Dispersion Chemistry (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261608240P | 2012-03-08 | 2012-03-08 | |
| US61/608,240 | 2012-03-08 | ||
| PCT/US2013/029582 WO2013134497A1 (en) | 2012-03-08 | 2013-03-07 | Viscosity suppression of associative thickeners using organophosphates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2866651A1 CA2866651A1 (en) | 2013-09-12 |
| CA2866651C true CA2866651C (en) | 2016-11-01 |
Family
ID=47913589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2866651A Active CA2866651C (en) | 2012-03-08 | 2013-03-07 | Viscosity suppression of associative thickeners using organophosphates |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9249280B2 (instruction) |
| EP (1) | EP2822994B1 (instruction) |
| JP (1) | JP6226893B2 (instruction) |
| CN (1) | CN104169352B (instruction) |
| AR (1) | AR090284A1 (instruction) |
| AU (1) | AU2013230911B2 (instruction) |
| BR (1) | BR112014022031B1 (instruction) |
| CA (1) | CA2866651C (instruction) |
| IN (1) | IN2014DN06924A (instruction) |
| MX (1) | MX345165B (instruction) |
| RU (1) | RU2633570C2 (instruction) |
| WO (1) | WO2013134497A1 (instruction) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2918266C (en) * | 2015-02-16 | 2023-03-28 | Rohm And Haas Company | Acid suppressible rheology modifier stabilized with phosphoric acid ester surfactant |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4155892A (en) | 1975-10-03 | 1979-05-22 | Rohm And Haas Company | Polyurethane thickeners for aqueous compositions |
| US4079028A (en) | 1975-10-03 | 1978-03-14 | Rohm And Haas Company | Polyurethane thickeners in latex compositions |
| EP0013491B1 (en) * | 1979-01-05 | 1982-10-20 | Imperial Chemical Industries Plc | Dispersions of siliceous solids in liquid organic media |
| US4428860A (en) * | 1979-10-22 | 1984-01-31 | Basf Wyandotte Corporation | Polyether thickeners for aqueous systems containing additives for increased thickening efficiency |
| US4327008A (en) | 1980-12-29 | 1982-04-27 | Ppg Industries, Inc. | Urethane rheology modifiers and coating compositions containing same |
| US4426485A (en) | 1982-06-14 | 1984-01-17 | Union Carbide Corporation | Polymers with hydrophobe bunches |
| US4499233A (en) | 1983-05-03 | 1985-02-12 | Nl Industries, Inc. | Water dispersible, modified polyurethane and a thickened aqueous composition containing it |
| US4496708A (en) | 1983-12-14 | 1985-01-29 | Union Carbide Corporation | Water-soluble polyurethane comb polymer production |
| US5023309A (en) | 1987-09-18 | 1991-06-11 | Rheox, Inc. | Water dispersible, modified polyurethane thickener with improved high shear viscosity in aqueous systems |
| US5137571A (en) | 1990-06-05 | 1992-08-11 | Rohm And Haas Company | Method for improving thickeners for aqueous systems |
| AU662511B2 (en) | 1991-02-08 | 1995-09-07 | Sherwin-Williams Company, The | Silicon-containing, hydrophobically-modified polyurethane thickeners |
| SE501624C2 (sv) | 1992-09-15 | 1995-04-03 | Berol Nobel Ab | Polyuretan, dess användning och vattenburen färg innehållande polyuretanen som förtjockare |
| US5281654A (en) | 1993-01-14 | 1994-01-25 | Rohm And Haas Company | Polyurethane mixture |
| US5376709A (en) | 1993-03-12 | 1994-12-27 | Rohm And Haas Company | Method for improving thickeners for aqueous systems |
| US5425806B1 (en) | 1994-05-12 | 1997-07-01 | Rheox Inc | Pourable water dispersible thickening composition for aqueous systems and a method of thickening said aqueous systems |
| US5574127A (en) | 1995-04-05 | 1996-11-12 | Aqualon | Hydrophobically modified poly(acetal-polyethers) |
| US5629373A (en) | 1995-06-07 | 1997-05-13 | United Catalysts, Inc. | Water based coating composition containing an aminoplast-ether copolymer |
| US5627232A (en) | 1995-06-07 | 1997-05-06 | United Catalysts, Inc. | Water-based composition containing an aminoplast-ether copolymer |
| US5914373A (en) | 1995-06-07 | 1999-06-22 | United Catalysts, Inc. | Water soluble aminoplast-ether copolymers |
| US6020407A (en) | 1995-11-07 | 2000-02-01 | Rheox, Inc. | Super dispersable thickening composition for aqueous systems and a method of thickening said aqueous systems |
| US5916935A (en) | 1996-08-27 | 1999-06-29 | Henkel Corporation | Polymeric thickeners for aqueous compositions |
| FR2766107B1 (fr) | 1997-07-18 | 1999-08-20 | Pluss Stauffer Ag | Suspensions aqueuses de matieres minerales et leurs utilisations |
| US6433056B1 (en) * | 1997-10-17 | 2002-08-13 | Hercules Incorporated | Fluidized polymer suspension of hydrophobically modified poly(acetal- or ketal-polyether) polyurethane and polyacrylate |
| SE512220C2 (sv) | 1998-06-30 | 2000-02-14 | Akzo Nobel Nv | Vattenhaltigt koncentrat av en associativ förtjockande polymer samt användning av en nonjonisk tensid för reduktion av koncentratets viskositet |
| US6162877A (en) | 1998-12-04 | 2000-12-19 | Hercules Incorporated | Hydrophobically modified comb copolymers |
| EP1208147A4 (en) | 1999-08-13 | 2002-10-16 | Sued Chemie Inc | COMPOSITION OF NON-IONIC ASSOCIATIVE THICKENERS WITH IMPROVED VISCOSITY RETENTION DURING NUAN AGE IN LATEX ARCHITECTURAL COATING |
| US6809132B2 (en) | 2001-10-29 | 2004-10-26 | Hercules Incorporated | Suppression of aqueous viscosity of associating polyacetal-polyethers |
| US6900255B2 (en) | 2003-05-16 | 2005-05-31 | Hercules Incorporated | Suppression of aqueous viscosity of nonionic associative thickeners |
| DE102004031786A1 (de) * | 2004-07-01 | 2006-01-26 | Cognis Deutschland Gmbh & Co. Kg | Verdickungsmittel auf Polyurethanbasis |
| US7531591B2 (en) * | 2004-12-09 | 2009-05-12 | Hercules Incorporated | Aqueous dispersion of poly(acetal-polyether) and its use in protective coatings |
| US7741402B2 (en) | 2007-03-21 | 2010-06-22 | Rohm And Haas Company | Thickener composition and method for thickening aqueous systems |
| AU2008255216B2 (en) * | 2008-01-07 | 2013-03-28 | Rohm And Haas Company | Fast dry, shelf stable-aqueous coating composition comprising a phosphorus acid polymer |
| CN102482517B (zh) * | 2009-07-02 | 2016-06-29 | 巴斯夫欧洲公司 | 无尖端干涸的低voc着色剂 |
| CN102741305B (zh) * | 2010-02-03 | 2015-02-25 | 巴斯夫欧洲公司 | 由酸单体、缔合性单体和非离子性单体制成的缔合性增稠剂 |
-
2013
- 2013-03-07 BR BR112014022031-0A patent/BR112014022031B1/pt active IP Right Grant
- 2013-03-07 MX MX2014010642A patent/MX345165B/es active IP Right Grant
- 2013-03-07 US US13/788,500 patent/US9249280B2/en active Active
- 2013-03-07 CN CN201380013100.1A patent/CN104169352B/zh active Active
- 2013-03-07 EP EP13711215.7A patent/EP2822994B1/en active Active
- 2013-03-07 IN IN6924DEN2014 patent/IN2014DN06924A/en unknown
- 2013-03-07 CA CA2866651A patent/CA2866651C/en active Active
- 2013-03-07 AU AU2013230911A patent/AU2013230911B2/en active Active
- 2013-03-07 RU RU2014140428A patent/RU2633570C2/ru active
- 2013-03-07 WO PCT/US2013/029582 patent/WO2013134497A1/en active Application Filing
- 2013-03-07 JP JP2014561108A patent/JP6226893B2/ja active Active
- 2013-03-08 AR ARP130100758A patent/AR090284A1/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| JP6226893B2 (ja) | 2017-11-08 |
| IN2014DN06924A (instruction) | 2015-04-10 |
| JP2015513602A (ja) | 2015-05-14 |
| EP2822994B1 (en) | 2015-12-30 |
| MX345165B (es) | 2017-01-19 |
| AU2013230911B2 (en) | 2016-02-25 |
| CN104169352B (zh) | 2016-08-31 |
| RU2633570C2 (ru) | 2017-10-13 |
| AR090284A1 (es) | 2014-10-29 |
| US9249280B2 (en) | 2016-02-02 |
| AU2013230911A1 (en) | 2014-09-04 |
| RU2014140428A (ru) | 2016-04-27 |
| WO2013134497A1 (en) | 2013-09-12 |
| CN104169352A (zh) | 2014-11-26 |
| EP2822994A1 (en) | 2015-01-14 |
| MX2014010642A (es) | 2014-12-05 |
| CA2866651A1 (en) | 2013-09-12 |
| US20130237651A1 (en) | 2013-09-12 |
| BR112014022031B1 (pt) | 2021-04-27 |
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