CA2181934C - Process for obtaining hydrophobically modified emulsion polymers, polymers obtained thereby, and waterborne coating compositions containing the polymers - Google Patents
Process for obtaining hydrophobically modified emulsion polymers, polymers obtained thereby, and waterborne coating compositions containing the polymers Download PDFInfo
- Publication number
- CA2181934C CA2181934C CA002181934A CA2181934A CA2181934C CA 2181934 C CA2181934 C CA 2181934C CA 002181934 A CA002181934 A CA 002181934A CA 2181934 A CA2181934 A CA 2181934A CA 2181934 C CA2181934 C CA 2181934C
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- core
- hydrophobic
- coating composition
- emulsion
- 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.)
- Expired - Fee Related
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 82
- 238000000034 method Methods 0.000 title claims abstract description 61
- 239000008199 coating composition Substances 0.000 title claims abstract description 56
- 239000004908 Emulsion polymer Substances 0.000 title claims abstract description 50
- 230000008569 process Effects 0.000 title claims abstract description 38
- 239000000178 monomer Substances 0.000 claims abstract description 75
- 239000000203 mixture Substances 0.000 claims abstract description 66
- 229920001600 hydrophobic polymer Polymers 0.000 claims abstract description 42
- 239000002245 particle Substances 0.000 claims abstract description 26
- 239000011258 core-shell material Substances 0.000 claims abstract description 18
- 238000007720 emulsion polymerization reaction Methods 0.000 claims abstract description 18
- 239000004094 surface-active agent Substances 0.000 claims abstract description 18
- 239000000758 substrate Substances 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 239000000049 pigment Substances 0.000 claims abstract description 7
- 239000004014 plasticizer Substances 0.000 claims abstract description 5
- 239000008346 aqueous phase Substances 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 28
- 230000002209 hydrophobic effect Effects 0.000 claims description 25
- -1 ethylene, propylene, butylene Chemical group 0.000 claims description 23
- 239000004814 polyurethane Substances 0.000 claims description 18
- 229920002635 polyurethane Polymers 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 125000000524 functional group Chemical group 0.000 claims description 15
- 239000000839 emulsion Substances 0.000 claims description 14
- 238000006116 polymerization reaction Methods 0.000 claims description 14
- 239000003431 cross linking reagent Substances 0.000 claims description 12
- 229920000728 polyester Polymers 0.000 claims description 9
- 229920000180 alkyd Polymers 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 229920000570 polyether Polymers 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 5
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 4
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims description 4
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000003827 glycol group Chemical group 0.000 claims 2
- DNZCDNLRZRLORF-UHFFFAOYSA-N 1-amino-3-hydroxy-1-phenoxyurea Chemical compound ONC(N(N)OC1=CC=CC=C1)=O DNZCDNLRZRLORF-UHFFFAOYSA-N 0.000 claims 1
- LDUOHXCVIFQGBK-UHFFFAOYSA-N carbonisocyanatidic acid Chemical compound OC(=O)N=C=O LDUOHXCVIFQGBK-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims 1
- 238000007717 redox polymerization reaction Methods 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 18
- 239000011248 coating agent Substances 0.000 abstract description 9
- 239000000463 material Substances 0.000 abstract description 3
- 239000004971 Cross linker Substances 0.000 abstract description 2
- 230000035882 stress Effects 0.000 description 22
- 229920005862 polyol Polymers 0.000 description 20
- 150000003077 polyols Chemical class 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 12
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 11
- 239000012948 isocyanate Substances 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
- 229960004063 propylene glycol Drugs 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 8
- 229910021641 deionized water Inorganic materials 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000005056 polyisocyanate Substances 0.000 description 8
- 229920001228 polyisocyanate Polymers 0.000 description 8
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 235000013772 propylene glycol Nutrition 0.000 description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 6
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- LZDXRPVSAKWYDH-UHFFFAOYSA-N 2-ethyl-2-(prop-2-enoxymethyl)propane-1,3-diol Chemical compound CCC(CO)(CO)COCC=C LZDXRPVSAKWYDH-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 238000004945 emulsification Methods 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920001281 polyalkylene Polymers 0.000 description 4
- 229920005749 polyurethane resin Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- 239000004593 Epoxy Chemical group 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000693 micelle Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
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- 230000000379 polymerizing effect Effects 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
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- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 2
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- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
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- 229920002633 Kraton (polymer) Polymers 0.000 description 2
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- 125000000129 anionic group Chemical group 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
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- 239000000194 fatty acid Substances 0.000 description 2
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- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
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- ZGDSDWSIFQBAJS-UHFFFAOYSA-N 1,2-diisocyanatopropane Chemical compound O=C=NC(C)CN=C=O ZGDSDWSIFQBAJS-UHFFFAOYSA-N 0.000 description 1
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- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- PIFZZXPFGWBEMD-UHFFFAOYSA-N 1-(1-prop-2-enoyloxypropan-2-ylperoxy)cyclohexane-1,2-dicarboxylic acid Chemical compound C(C=C)(=O)OCC(OOC1(C(=O)O)C(C(=O)O)CCCC1)C PIFZZXPFGWBEMD-UHFFFAOYSA-N 0.000 description 1
- ZVEMLYIXBCTVOF-UHFFFAOYSA-N 1-(2-isocyanatopropan-2-yl)-3-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC(C(C)(C)N=C=O)=C1 ZVEMLYIXBCTVOF-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
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- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 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
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
-
- 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
- C08F285/00—Macromolecular compounds obtained by polymerising monomers on to preformed graft polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
- C08J3/126—Polymer particles coated by polymer, e.g. core shell structures
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Paints Or Removers (AREA)
- Graft Or Block Polymers (AREA)
- Polymerisation Methods In General (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/506,143 | 1995-07-24 | ||
| US08/506,143 US5569715A (en) | 1995-07-24 | 1995-07-24 | Process for obtaining hydrophobically modified emulsion polymers and polymers obtained thereby |
| US08/506,142 | 1995-07-24 | ||
| US08/506,142 US5969030A (en) | 1995-07-24 | 1995-07-24 | Waterborne coating compositions containing hydrophobically modified emulsions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2181934A1 CA2181934A1 (en) | 1997-01-25 |
| CA2181934C true CA2181934C (en) | 2005-04-05 |
Family
ID=27055377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002181934A Expired - Fee Related CA2181934C (en) | 1995-07-24 | 1996-07-23 | Process for obtaining hydrophobically modified emulsion polymers, polymers obtained thereby, and waterborne coating compositions containing the polymers |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5786420A (enExample) |
| EP (1) | EP0755946A3 (enExample) |
| JP (1) | JPH09221506A (enExample) |
| KR (1) | KR970006333A (enExample) |
| CN (1) | CN1146996A (enExample) |
| AU (1) | AU692399B2 (enExample) |
| CA (1) | CA2181934C (enExample) |
Families Citing this family (78)
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|---|---|---|---|---|
| US6384110B1 (en) * | 1995-08-15 | 2002-05-07 | Georgia Tech Research Corporation | Water-borne polyurethane coatings by miniemulsion polymerization |
| US6369135B1 (en) * | 1995-08-15 | 2002-04-09 | Georgia Tech Research Corporation | Water-borne alkyd coatings by miniemulsion polymerization |
| US6380281B1 (en) * | 1996-08-13 | 2002-04-30 | Georgia Tech Research Corporation | Water-borne polyester coatings by miniemulsion polymerization |
| JPH10339951A (ja) * | 1997-06-09 | 1998-12-22 | Toyobo Co Ltd | 感光性樹脂組成物 |
| US6333378B1 (en) * | 1997-08-12 | 2001-12-25 | Eastman Chemical Company | Acrylic modified waterborne alkyd or uralkyd dispersions |
| KR100538846B1 (ko) * | 1997-12-31 | 2006-03-27 | 주식회사 케이씨씨 | 알킬렌모노이소시아네이트/폴리(에틸렌 옥사이드)모노알콜 단량체가 포함된 코어/쉘형 마이크로겔 및 이를 함유한 도료 조성물 |
| DE19833061A1 (de) * | 1998-07-22 | 2000-02-03 | Elotex Ag Sempach Station | Verfahren zur Herstellung wäßriger Dispersionen von Latexteilchen mit heterogener Morphologie, die mit dem Verfahren erhältlichen Latexteilchen, die Dispersionen und redispergierbaren Pulver sowie deren Verwendung |
| US6180181B1 (en) | 1998-12-14 | 2001-01-30 | Ppg Industries Ohio, Inc. | Methods for forming composite coatings on substrates |
| DE19918133A1 (de) * | 1999-04-21 | 2000-11-16 | Ppg Ind Lacke Gmbh | Polymer |
| DE19918137A1 (de) * | 1999-04-21 | 2000-10-26 | Ppg Ind Lacke Gmbh | Polymer |
| KR20020012181A (ko) | 1999-04-21 | 2002-02-15 | 피피지 인더스트리즈 락케 게엠베하 | 중합체 |
| DE19930067A1 (de) | 1999-06-30 | 2001-01-11 | Basf Coatings Ag | Beschichtungsstoff und seine Verwendung zur Herstellung von Füllerschichten und Steinschlagschutzgrundierungen |
| DE19930066A1 (de) | 1999-06-30 | 2001-01-11 | Basf Coatings Ag | Farb- und/oder effektgebende Mehrschichtlackierung, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19930664A1 (de) | 1999-07-02 | 2001-01-11 | Basf Coatings Ag | Klarlack und seine Verwendung zur Herstellung von Klarlackierungen und farb- und/oder effektgebenden Mehrschichtlackierungen |
| DE19930665A1 (de) | 1999-07-02 | 2001-01-11 | Basf Coatings Ag | Basislack und seine Verwendung zur Herstellung von farb- und/oder effektgebenden Basislackierungen und Mehrschichtlackierung |
| AU779679B2 (en) * | 1999-11-09 | 2005-02-03 | Rohm And Haas Company | Emulsion polymers |
| DE19959927A1 (de) | 1999-12-11 | 2002-02-07 | Basf Coatings Ag | Wäßrige Primärdispersionen und Beschichtungsstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19959923A1 (de) | 1999-12-11 | 2001-06-28 | Basf Coatings Ag | Wäßrige Primärdispersionen und Beschichtungsstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10005819A1 (de) | 2000-02-10 | 2001-08-23 | Basf Coatings Ag | Wäßrige Primärdispersionen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10018078A1 (de) | 2000-04-12 | 2001-11-08 | Basf Coatings Ag | Formmassen und Verfahren zur Herstellung von Formkörpern |
| DE10018601A1 (de) * | 2000-04-14 | 2001-10-25 | Basf Coatings Ag | Wäßrige Primärdispersionen und Beschichtungsstoffe, 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 |
| DE10029803A1 (de) | 2000-06-16 | 2002-01-03 | Basf Coatings Ag | Copolymerisate und Copolymerisatdispersionen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US6881791B2 (en) | 2000-06-16 | 2005-04-19 | Basf Corporation | Poly-electrolyte free block copolymers and their use in crosslinking coatings applications |
| US6699943B2 (en) | 2000-06-16 | 2004-03-02 | Basf Corporation | Water-based coating composition having carbamate-melamine cross-linking, method of preparing the same, and a cured film thereof |
| US6391973B1 (en) | 2000-07-24 | 2002-05-21 | Basf Corporation | Curable coating composition with improved stability |
| DE10039262B4 (de) | 2000-08-11 | 2006-03-30 | Basf Coatings Ag | Polyurethane, Verfahren zu deren Herstellung, sowie ihre Verwendung zur Herstellung von Pfropfmischpolymerisaten, Beschichtungsstoffen, Klebstoffen und Dichtungsmassen |
| DE10043405C1 (de) * | 2000-09-04 | 2002-06-27 | Basf Coatings Ag | Verfahren zur Herstellung farb- und/oder effektgebender Lackierungen |
| DE10053890A1 (de) | 2000-10-31 | 2002-05-16 | Basf Coatings Ag | Sulfidgruppen enthaltende Polyurethane und Polymergemische auf dieser Basis sowie ihre Herstellung und ihre Verwendung |
| AU2002245114B2 (en) * | 2000-11-02 | 2007-08-30 | Erdem Bedri | Process for preparing aqueous dispersions of hybrid polyurethane particles |
| US7226971B2 (en) * | 2000-12-22 | 2007-06-05 | Basf Corporation | Polyester resin with carbamate functionality, a method of preparing the resin, and a coating composition utilizing the resin |
| US6657002B2 (en) | 2000-12-22 | 2003-12-02 | Basf Corporation | Polymeric pigment dispersant utilized as a grind resin for pigments and method of preparing the same |
| US6642338B2 (en) | 2000-12-22 | 2003-11-04 | Basf Corporation | Water-based acrylic emulsion dispersants utilized as grind resins for pigments and method of preparing the same |
| US6849686B2 (en) * | 2000-12-22 | 2005-02-01 | Basf Corporation | Polymeric pigment dispersant utilized as a grind resin for pigments and method of preparing the same |
| US7005473B2 (en) * | 2000-12-22 | 2006-02-28 | Basf Corporation | Polymeric pigment dispersant utilized as a grind resin for pigments in solventborne pigment dispersions and method of preparing the same |
| BR0114925A (pt) * | 2000-12-22 | 2003-12-23 | Basf Corp | Composição de revestimento à base de água que apresenta reticulação carbonato-amina, método de preparação dessa composição, e uma pelìcula curada dos mesmos |
| US6573313B2 (en) * | 2001-01-16 | 2003-06-03 | The Hong Kong Polytechnic University | Amphiphilic core-shell latexes |
| DE10106566A1 (de) * | 2001-02-13 | 2002-08-22 | Basf Coatings Ag | Von flüchtigen organischen Stoffen im wesentlichen oder völlig freier wäßriger Beschichtungsstoff, Verfahren zu seiner Herstellung und seine Verwendung |
| DE10106567A1 (de) * | 2001-02-13 | 2002-08-22 | Basf Coatings Ag | Von flüchtigen organischen Stoffen im wesentlichen oder völlig freie wäßrige Primärdispersion, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US6861150B2 (en) | 2001-02-26 | 2005-03-01 | Basf Corporation | Rheology control agent, a method of preparing the agent, and a coating composition utilizing the agent |
| DE10115592A1 (de) | 2001-03-29 | 2002-10-10 | Basf Coatings Ag | Von flüchtigen organischen Verbindungen freie oder im wesentlichen freie, wäßrige Dispersionen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10115602A1 (de) | 2001-03-29 | 2002-10-24 | Basf Coatings Ag | Mit Polyurethanen modifizierte Copolymerisate, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US6761774B2 (en) | 2001-05-24 | 2004-07-13 | Basf Corporation | Composition and method for the in situ removal scale from a substrate |
| DE10126651A1 (de) | 2001-06-01 | 2002-12-12 | Basf Coatings Ag | Pulverlacksuspensionen (Pulverslurries) und Pulverlacke, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US6683145B2 (en) | 2001-10-26 | 2004-01-27 | Basf Corporation | Hydrophobic lattices and coating compositions containing them |
| US20050228124A1 (en) * | 2002-04-19 | 2005-10-13 | Shanti Swarup | Coating compositions containing highly crosslinked polymer particles and a hydrophobic polymer |
| US7001952B2 (en) * | 2002-04-19 | 2006-02-21 | Ppg Industries Ohio, Inc. | Coating compositions containing polyurethane dispersions and highly crosslinked polymer particles |
| US6762240B2 (en) | 2002-04-19 | 2004-07-13 | Ppg Industries Ohio, Inc. | Highly crosslinked polymer particles and coating compositions containing the same |
| US6858301B2 (en) * | 2003-01-02 | 2005-02-22 | Hewlett-Packard Development Company, L.P. | Specific core-shell polymer additive for ink-jet inks to improve durability |
| US7705070B2 (en) | 2003-02-06 | 2010-04-27 | Hewlett-Packard Development Company, L.P. | Ink-jet compatible latexes |
| US7402617B2 (en) * | 2003-02-06 | 2008-07-22 | Hewlett-Packard Development Company, L.P. | Low bulk density, low surface dielectric constant latex polymers for ink-jet ink applications |
| GB0409570D0 (en) * | 2004-04-29 | 2004-06-02 | Ciba Spec Chem Water Treat Ltd | Particulate compositions and their manufacture |
| US20060270769A1 (en) * | 2005-05-24 | 2006-11-30 | Shoaf Glenn L | Acrylic-modified alkyd hybrid latexes and their use as viscosity modifiers |
| JP4788436B2 (ja) * | 2006-03-29 | 2011-10-05 | 日本電気株式会社 | 無線リソース割り当て方法及びそれを用いる無線リソース割り当て装置並びに基地局 |
| US8283403B2 (en) * | 2006-03-31 | 2012-10-09 | Applied Nanotech Holdings, Inc. | Carbon nanotube-reinforced nanocomposites |
| US20110160346A1 (en) * | 2006-03-31 | 2011-06-30 | Applied Nanotech Holdings, Inc. | Dispersion of carbon nanotubes by microfluidic process |
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| US8129463B2 (en) * | 2006-03-31 | 2012-03-06 | Applied Nanotech Holdings, Inc. | Carbon nanotube-reinforced nanocomposites |
| US20070276077A1 (en) * | 2006-04-05 | 2007-11-29 | Nano-Proprietary, Inc. | Composites |
| US8445587B2 (en) * | 2006-04-05 | 2013-05-21 | Applied Nanotech Holdings, Inc. | Method for making reinforced polymer matrix composites |
| US7544418B2 (en) * | 2006-07-31 | 2009-06-09 | Hewlett-Packard Development Company, L.P. | Polymer-encapsulated pigments and associated methods |
| US9156956B2 (en) * | 2007-01-31 | 2015-10-13 | Hewlett-Packard Development Company, L.P. | Surface-crosslinked latex particulates |
| ES2372663T3 (es) * | 2008-12-29 | 2012-01-25 | Rohm And Haas Company | Pinturas de emulsión alquídica extendida de alto brillo. |
| JP5852301B2 (ja) * | 2009-07-02 | 2016-02-03 | キヤノン株式会社 | クリアインク、インクジェット記録方法、インクセット、インクカートリッジ、記録ユニット、及びインクジェット記録装置 |
| US8329822B2 (en) * | 2009-11-09 | 2012-12-11 | E.I. Du Pont De Nemours And Company | Fluoropolymer emulsions |
| JP5882628B2 (ja) * | 2010-08-31 | 2016-03-09 | キヤノン株式会社 | インク、インクカートリッジ、及びインクジェット記録方法 |
| US9034964B2 (en) * | 2010-10-21 | 2015-05-19 | Eastman Chemical Company | Waterborne coating compositions containing low-VOC coalescents that are hydroxypivalyl hydroxypivalate esters |
| EP2450410B1 (en) * | 2010-11-08 | 2013-07-03 | Rohm and Haas Company | Hase-thickened composition |
| JP5922884B2 (ja) * | 2011-06-21 | 2016-05-24 | ジャパンコーティングレジン株式会社 | 複合樹脂水性分散液 |
| EP3016868B1 (en) | 2013-07-02 | 2023-09-27 | Swimc Llc | Coating compositions for packaging articles such as food and beverage containers |
| KR101884537B1 (ko) | 2013-07-02 | 2018-08-01 | 발스파 소싱 인코포레이티드 | 식품 및 음료 용기와 같은 패키징 물품을 위한 코팅 조성물 |
| NO340788B1 (no) * | 2014-09-17 | 2017-06-19 | Wellcem Innovation As | Forbedret fremgangsmåte og kjemisk middel for reduksjon av vannproduksjon fra olje- og gassholdige brønner |
| US20160104556A1 (en) | 2014-10-10 | 2016-04-14 | Elantas Pdg, Inc. | Emulsions with improved stability |
| US11554385B2 (en) | 2015-11-17 | 2023-01-17 | Ppg Industries Ohio, Inc. | Coated substrates prepared with waterborne sealer and primer compositions |
| FR3064193B1 (fr) * | 2017-03-21 | 2021-04-30 | Calyxia | Procede de preparation de capsules avec des proprietes de retention ameliorees et capsules obtenues |
| JP7114904B2 (ja) * | 2018-01-16 | 2022-08-09 | 三菱ケミカル株式会社 | 水性樹脂分散体含有混合物とその製造方法及び塗装物 |
| CN112608414B (zh) * | 2020-07-28 | 2022-09-06 | 杭州传化精细化工有限公司 | 一种含氟共聚物乳液及其制备方法与应用 |
| CN119331580A (zh) * | 2024-04-30 | 2025-01-21 | 中国石油天然气集团有限公司 | 一种抗高温无固相钻井液及其制备方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO140932C (no) * | 1977-08-10 | 1979-12-12 | Sintef | Fremgangsmaate for fremstilling av lateks |
| AU530410B2 (en) * | 1978-02-21 | 1983-07-14 | Sintef | Preparing aqueous emulsions |
| JPS57179860A (en) * | 1981-04-30 | 1982-11-05 | Fuji Photo Film Co Ltd | Capsulate toner |
| US4469825A (en) * | 1983-03-09 | 1984-09-04 | Rohm And Haas Company | Sequential heteropolymer dispersion and a particulate material obtainable therefrom, useful in coating compositions as an opacifying agent |
| US4677003A (en) * | 1985-04-30 | 1987-06-30 | Rohm And Haas Company | Microsuspension process for preparing solvent core sequential polymer dispersion |
| US4918123A (en) * | 1988-05-17 | 1990-04-17 | Exxon Chemical Patents, Inc. | Inverse emulsion process for preparing hydrophobe-containing polymers |
| US5021381A (en) * | 1988-08-24 | 1991-06-04 | The Goodyear Tire & Rubber Company | Syndiotactic 1,2-polybutadiene latex |
| US5266646A (en) * | 1989-05-15 | 1993-11-30 | Rohm And Haas Company | Multi-stage polymer particles having a hydrophobically-modified, ionically-soluble stage |
| US5071904A (en) * | 1989-05-30 | 1991-12-10 | Ppg Industries, Inc. | Waterborne coating compositions for automotive applications |
| US5238992A (en) * | 1989-08-30 | 1993-08-24 | Edison Polymer Innovation Corporation | Microemulsion polymer blends |
| US5213044A (en) * | 1990-11-30 | 1993-05-25 | Como Technologies, Incorporated | Method and apparatus for use in printing |
| US5405879A (en) * | 1991-04-05 | 1995-04-11 | Nippon Carbide Kogyo Kabushiki Kaisha | Aqueous dispersion of acrylic polymer |
| US5264315A (en) * | 1992-04-20 | 1993-11-23 | Xerox Corporation | Process for the continuous preparation of encapsulated toner |
| US5338345A (en) * | 1993-05-05 | 1994-08-16 | Eastman Kodak Company | Water-based water repellent coating compositions |
| US5569715A (en) * | 1995-07-24 | 1996-10-29 | Basf Corporation | Process for obtaining hydrophobically modified emulsion polymers and polymers obtained thereby |
-
1996
- 1996-07-12 EP EP96111255A patent/EP0755946A3/en not_active Ceased
- 1996-07-22 AU AU60635/96A patent/AU692399B2/en not_active Ceased
- 1996-07-23 CN CN96111103A patent/CN1146996A/zh active Pending
- 1996-07-23 CA CA002181934A patent/CA2181934C/en not_active Expired - Fee Related
- 1996-07-24 JP JP8195068A patent/JPH09221506A/ja active Pending
- 1996-07-24 KR KR1019960029919A patent/KR970006333A/ko not_active Abandoned
- 1996-07-26 US US08/690,669 patent/US5786420A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2181934A1 (en) | 1997-01-25 |
| JPH09221506A (ja) | 1997-08-26 |
| EP0755946A2 (en) | 1997-01-29 |
| CN1146996A (zh) | 1997-04-09 |
| US5786420A (en) | 1998-07-28 |
| AU692399B2 (en) | 1998-06-04 |
| EP0755946A3 (en) | 1997-10-01 |
| AU6063596A (en) | 1997-01-30 |
| KR970006333A (ko) | 1997-02-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |