CA2352053C - Hydrophobically modified comb copolymers - Google Patents
Hydrophobically modified comb copolymers Download PDFInfo
- Publication number
- CA2352053C CA2352053C CA002352053A CA2352053A CA2352053C CA 2352053 C CA2352053 C CA 2352053C CA 002352053 A CA002352053 A CA 002352053A CA 2352053 A CA2352053 A CA 2352053A CA 2352053 C CA2352053 C CA 2352053C
- Authority
- CA
- Canada
- Prior art keywords
- comb copolymer
- molecular weight
- compound
- copolymer according
- hydrophobe
- 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 - Lifetime
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 195
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- 239000003973 paint Substances 0.000 claims abstract description 28
- 239000004816 latex Substances 0.000 claims abstract description 13
- 229920000126 latex Polymers 0.000 claims abstract description 13
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- -1 poly(acrylic acid) Polymers 0.000 claims description 60
- 230000002209 hydrophobic effect Effects 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 34
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 229920003169 water-soluble polymer Polymers 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 229940058344 antitrematodals organophosphorous compound Drugs 0.000 claims description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 9
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 9
- 125000003367 polycyclic group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- 150000001491 aromatic compounds Chemical class 0.000 claims description 7
- GATVIKZLVQHOMN-UHFFFAOYSA-N Chlorodibromomethane Chemical group ClC(Br)Br GATVIKZLVQHOMN-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 6
- 229920002873 Polyethylenimine Polymers 0.000 claims description 5
- 229920002125 Sokalan® Polymers 0.000 claims description 5
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 5
- 239000008199 coating composition Substances 0.000 claims description 5
- 229920002401 polyacrylamide Polymers 0.000 claims description 5
- 229920001184 polypeptide Polymers 0.000 claims description 5
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 5
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 3
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 2
- 150000002902 organometallic compounds Chemical class 0.000 claims 1
- 239000002562 thickening agent Substances 0.000 abstract description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
- 239000000243 solution Substances 0.000 description 22
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 21
- 125000000913 palmityl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
- 238000000576 coating method Methods 0.000 description 13
- 229920000570 polyether Polymers 0.000 description 13
- 239000002585 base Substances 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- 239000012312 sodium hydride Substances 0.000 description 9
- 239000004721 Polyphenylene oxide Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000002480 mineral oil Substances 0.000 description 7
- 235000010446 mineral oil Nutrition 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 229920001897 terpolymer Polymers 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 150000004676 glycans Chemical class 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- ZIAHZFPHXNQNQN-UHFFFAOYSA-N 1-(dibromomethyl)-3-fluorobenzene Chemical compound FC1=CC=CC(C(Br)Br)=C1 ZIAHZFPHXNQNQN-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229920001282 polysaccharide Polymers 0.000 description 4
- 239000005017 polysaccharide Substances 0.000 description 4
- 230000008719 thickening Effects 0.000 description 4
- 229920002594 Polyethylene Glycol 8000 Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 3
- 229920001477 hydrophilic polymer Polymers 0.000 description 3
- 125000001165 hydrophobic group Chemical group 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000007665 sagging Methods 0.000 description 3
- 238000001542 size-exclusion chromatography Methods 0.000 description 3
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 2
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
- LBUNNMJLXWQQBY-UHFFFAOYSA-N 4-fluorophenylboronic acid Chemical compound OB(O)C1=CC=C(F)C=C1 LBUNNMJLXWQQBY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- ZTISUHQLYYPYFA-UHFFFAOYSA-N [5-(hydroxymethyl)-1,3-dioxan-5-yl]methanol Chemical compound OCC1(CO)COCOC1 ZTISUHQLYYPYFA-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical compound CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
- 229940106691 bisphenol a Drugs 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 239000006254 rheological additive Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- AKXKKSAGNHWXPQ-UHFFFAOYSA-N 1,2-dibromo-3,4-dimethylbenzene Chemical group CC1=CC=C(Br)C(Br)=C1C AKXKKSAGNHWXPQ-UHFFFAOYSA-N 0.000 description 1
- UZPZYFDULMKDMB-UHFFFAOYSA-N 1,2-dichloro-3,4-dimethylbenzene Chemical compound CC1=CC=C(Cl)C(Cl)=C1C UZPZYFDULMKDMB-UHFFFAOYSA-N 0.000 description 1
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000870659 Crassula perfoliata var. minor Species 0.000 description 1
- 229920000896 Ethulose Polymers 0.000 description 1
- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000161 Locust bean gum Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- IWWCATWBROCMCW-UHFFFAOYSA-N batyl alcohol Natural products CCCCCCCCCCCCCCCCCCOC(O)CO IWWCATWBROCMCW-UHFFFAOYSA-N 0.000 description 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical class OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 239000007805 chemical reaction reactant Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- NOIURJTUGBYOLG-UHFFFAOYSA-N dichloromethyl-dimethyl-propylsilane Chemical compound CCC[Si](C)(C)C(Cl)Cl NOIURJTUGBYOLG-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 1
- PBJZAYSKNIIHMZ-UHFFFAOYSA-N ethyl carbamate;oxirane Chemical class C1CO1.CCOC(N)=O PBJZAYSKNIIHMZ-UHFFFAOYSA-N 0.000 description 1
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229920013746 hydrophilic polyethylene oxide Polymers 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000976 ink 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
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 239000000711 locust bean gum Substances 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010297 mechanical methods and process Methods 0.000 description 1
- 230000005226 mechanical processes and functions Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003129 oil well Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 150000004804 polysaccharides Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000004711 α-olefin Substances 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
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
- C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Dispersion Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Polyethers (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/209,373 | 1998-12-04 | ||
| US09/209,373 US6162877A (en) | 1998-12-04 | 1998-12-04 | Hydrophobically modified comb copolymers |
| PCT/US1999/028135 WO2000034361A1 (en) | 1998-12-04 | 1999-11-24 | Hydrophobically modified comb copolymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2352053A1 CA2352053A1 (en) | 2000-06-15 |
| CA2352053C true CA2352053C (en) | 2008-12-02 |
Family
ID=22778514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002352053A Expired - Lifetime CA2352053C (en) | 1998-12-04 | 1999-11-24 | Hydrophobically modified comb copolymers |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6162877A (enExample) |
| EP (1) | EP1135428B1 (enExample) |
| JP (1) | JP4459447B2 (enExample) |
| CN (1) | CN100368462C (enExample) |
| AR (1) | AR023718A1 (enExample) |
| AT (1) | ATE318280T1 (enExample) |
| AU (1) | AU1833500A (enExample) |
| BR (1) | BR9915936A (enExample) |
| CA (1) | CA2352053C (enExample) |
| CO (1) | CO5121084A1 (enExample) |
| DE (1) | DE69930003T2 (enExample) |
| ES (1) | ES2255323T3 (enExample) |
| ID (1) | ID29033A (enExample) |
| MY (1) | MY122401A (enExample) |
| TW (1) | TW580506B (enExample) |
| WO (1) | WO2000034361A1 (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2811083B1 (fr) * | 2000-06-30 | 2002-11-22 | Inst Curie | Milieu liquide non-thermosensible pour l'analyse d'especes au sein d'un canal |
| FR2810905B1 (fr) * | 2000-06-30 | 2003-05-16 | Inst Curie | Additif pour minimiser les phenomenes d'adsorption et/ou d'electroosmose |
| US8975328B2 (en) * | 2000-06-30 | 2015-03-10 | Institute Curie | Non-thermosensitive medium for analyzing species in a channel and for minimizing adsorption and/or electroosomosic phenomena |
| 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 |
| CN1946815B (zh) * | 2004-01-08 | 2015-06-17 | 赫尔克里士公司 | 着色剂相容性涂料用合成增稠剂 |
| JP4746845B2 (ja) * | 2004-04-14 | 2011-08-10 | 株式会社ニッコー化学研究所 | 重合体溶液、艶消し塗料及び化粧シート |
| US7531591B2 (en) * | 2004-12-09 | 2009-05-12 | Hercules Incorporated | Aqueous dispersion of poly(acetal-polyether) and its use in protective coatings |
| ES2389776T3 (es) * | 2005-05-31 | 2012-10-31 | Rhodia, Inc. | Composiciones que tienen modificadores reológicos HASE |
| WO2007084126A1 (en) * | 2006-01-19 | 2007-07-26 | Allexcel, Inc. | Solubilization and targeted delivery of drugs with self-assembling amphiphilic polymers |
| WO2007124142A2 (en) * | 2006-04-19 | 2007-11-01 | Hercules Incorporated | Stabilizers for improved open time of aqueous coatings |
| US7741402B2 (en) * | 2007-03-21 | 2010-06-22 | Rohm And Haas Company | Thickener composition and method for thickening aqueous systems |
| US8286561B2 (en) | 2008-06-27 | 2012-10-16 | Ssw Holding Company, Inc. | Spill containing refrigerator shelf assembly |
| US11786036B2 (en) | 2008-06-27 | 2023-10-17 | Ssw Advanced Technologies, Llc | Spill containing refrigerator shelf assembly |
| JP2011528400A (ja) | 2008-07-17 | 2011-11-17 | ハーキュリーズ・インコーポレーテッド | 水系コーティング組成物を調整する方法 |
| WO2010042668A1 (en) | 2008-10-07 | 2010-04-15 | Ross Technology Corporation | Spill resistant surfaces having hydrophobic and oleophobic borders |
| KR101687290B1 (ko) * | 2009-03-27 | 2016-12-16 | 허큘레스 엘엘씨 | 아미노화된 중합체 및 수성 조성물에서 그의 사용 |
| US20100324177A1 (en) * | 2009-06-18 | 2010-12-23 | Bakeev Kirill N | Colorant compatible hydrophobically modified polyethyleneglycol thickener for paint |
| ES2613885T3 (es) | 2009-11-04 | 2017-05-26 | Ssw Holding Company, Inc. | Superficies de aparatos de cocción que tienen un patrón de confinamiento de salpicaduras y procedimientos de fabricación de las mismas |
| CN102858814B (zh) * | 2010-02-12 | 2015-07-15 | 罗地亚管理公司 | 具有冻融稳定性的组合物 |
| WO2011100071A1 (en) | 2010-02-12 | 2011-08-18 | Rhodia Operations | Rheology modifier polymer |
| EP2534205B1 (en) | 2010-02-12 | 2016-05-04 | Rhodia Operations | Rheology modifier compositions and methods of use |
| MX2012010669A (es) | 2010-03-15 | 2013-02-07 | Ross Technology Corp | Destacadores y metodos para producir supreficies hidrofobas. |
| MX2013009609A (es) | 2011-02-21 | 2013-09-16 | Ross Technology Corp | Revestimiento suoerhidrofobos y oleofobos con sistemas aglutinantes con bajo contenido de compuestos organicos volatiles. |
| DE102011085428A1 (de) | 2011-10-28 | 2013-05-02 | Schott Ag | Einlegeboden |
| EP2791255B1 (en) | 2011-12-15 | 2017-11-01 | Ross Technology Corporation | Composition and coating for superhydrophobic performance |
| BR112014022031B1 (pt) | 2012-03-08 | 2021-04-27 | Hercules Incorporated | Composição de espessante associativo compreendendo organofosfatos |
| CN104520392A (zh) | 2012-06-25 | 2015-04-15 | 罗斯科技公司 | 具有疏水和/或疏油性质的弹性体涂层 |
| US9718920B2 (en) | 2012-12-19 | 2017-08-01 | 3M Innovative Properties Company | Reactive polyoxazolines having a perfluorinated group |
| US9556340B2 (en) * | 2012-12-19 | 2017-01-31 | 3M Innovative Properties Company | Polyoxazoline copolymers |
| US10358574B2 (en) | 2016-07-01 | 2019-07-23 | Hercules Llc | Coating compositions containing lactam-functionalized polymer |
| PL3478663T3 (pl) | 2016-07-01 | 2021-05-04 | Hercules Llc | Polimer funkcjonalizowany laktamem, jego kompozycje i zastosowanie |
| JP6886368B2 (ja) * | 2017-08-22 | 2021-06-16 | 信越ポリマー株式会社 | 硬化性組成物および帯電防止シリコーン皮膜 |
| MX2020009799A (es) | 2018-03-21 | 2020-10-12 | Nouryon Chemicals Int Bv | Recubrimientos con propiedades reflectantes solares. |
| CN108727594A (zh) * | 2018-07-04 | 2018-11-02 | 吴依龙 | 一种梳形支化有机硅共聚物及制作方法 |
| CN113302247A (zh) | 2019-01-11 | 2021-08-24 | 诺力昂化学品国际有限公司 | 耐沾污涂层 |
| FR3134097B1 (fr) * | 2022-04-01 | 2025-11-21 | Coatex Sas | Préparation continue de composé polyéther hydrophobe |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4079028A (en) * | 1975-10-03 | 1978-03-14 | Rohm And Haas Company | Polyurethane thickeners in latex compositions |
| US4155892A (en) * | 1975-10-03 | 1979-05-22 | Rohm And Haas Company | Polyurethane thickeners for aqueous compositions |
| US4228277A (en) * | 1979-02-12 | 1980-10-14 | Hercules Incorporated | Modified nonionic cellulose ethers |
| US4243802A (en) * | 1979-06-06 | 1981-01-06 | Hercules Incorporated | Surfactant-soluble cellulose derivatives |
| US4288639A (en) * | 1979-10-22 | 1981-09-08 | Basf Wyandotte Corporation | Alpha-olefin oxide-modified liquid polyether thickeners |
| US4354956A (en) * | 1979-10-22 | 1982-10-19 | Basf Wyandotte Corporation | Thickening aqueous systems with alpha-olefin oxide-modified liquid polyether thickeners |
| US4428860A (en) * | 1979-10-22 | 1984-01-31 | Basf Wyandotte Corporation | Polyether thickeners for aqueous systems containing additives for increased thickening efficiency |
| US4411819A (en) * | 1979-10-22 | 1983-10-25 | Basf Wyandotte Corporation | Thickening aqueous compositions with polyethers modified with alpha-olefin oxides |
| US4312775A (en) * | 1979-10-22 | 1982-01-26 | 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 |
| US4380610A (en) * | 1981-12-21 | 1983-04-19 | Conoco Inc. | Polyacetal comb polymers |
| 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 |
| DE3643459A1 (de) * | 1986-12-19 | 1988-06-23 | Bayer Ag | Polyethersiloxan - pfropfpolymerisate |
| US4870167A (en) * | 1987-03-02 | 1989-09-26 | Hi-Tek Polymers, Inc. | Hydrophobically modified non-ionic polygalactomannan ethers |
| US5023309A (en) * | 1987-09-18 | 1991-06-11 | Rheox, Inc. | Water dispersible, modified polyurethane thickener with improved high shear viscosity in aqueous systems |
| US4847332A (en) * | 1987-12-07 | 1989-07-11 | The B. F. Goodrich Company | Terminally unsaturated macromolecular monomers of polyformals and copolymers thereof |
| DE3829839A1 (de) * | 1988-09-02 | 1990-03-08 | Akzo Gmbh | Verdickungsmittel fuer waessrige systeme |
| JP2002517169A (ja) * | 1990-11-08 | 2002-06-11 | ヘンケル・コーポレイション | 水性組成物用ポリマー増粘剤 |
| 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 |
| US5290418A (en) * | 1992-09-24 | 1994-03-01 | Applied Biosystems, Inc. | Viscous electrophoresis polymer medium and method |
| US5281654A (en) * | 1993-01-14 | 1994-01-25 | Rohm And Haas Company | Polyurethane mixture |
| US5574127A (en) * | 1995-04-05 | 1996-11-12 | Aqualon | Hydrophobically modified poly(acetal-polyethers) |
| US5556460A (en) * | 1995-09-18 | 1996-09-17 | W.R. Grace & Co.-Conn. | Drying shrinkage cement admixture |
| EP0898610B1 (en) * | 1996-04-16 | 2002-10-09 | The Procter & Gamble Company | Detergent compositions containing selected mid-chain branched surfactants |
-
1998
- 1998-12-04 US US09/209,373 patent/US6162877A/en not_active Expired - Lifetime
-
1999
- 1999-11-24 BR BR9915936-8A patent/BR9915936A/pt not_active Application Discontinuation
- 1999-11-24 ID IDW00200101457A patent/ID29033A/id unknown
- 1999-11-24 AT AT99961837T patent/ATE318280T1/de not_active IP Right Cessation
- 1999-11-24 WO PCT/US1999/028135 patent/WO2000034361A1/en not_active Ceased
- 1999-11-24 EP EP99961837A patent/EP1135428B1/en not_active Expired - Lifetime
- 1999-11-24 CA CA002352053A patent/CA2352053C/en not_active Expired - Lifetime
- 1999-11-24 DE DE69930003T patent/DE69930003T2/de not_active Expired - Lifetime
- 1999-11-24 CN CNB998140686A patent/CN100368462C/zh not_active Expired - Lifetime
- 1999-11-24 AU AU18335/00A patent/AU1833500A/en not_active Abandoned
- 1999-11-24 ES ES99961837T patent/ES2255323T3/es not_active Expired - Lifetime
- 1999-11-24 JP JP2000586802A patent/JP4459447B2/ja not_active Expired - Lifetime
- 1999-12-03 TW TW088121200A patent/TW580506B/zh not_active IP Right Cessation
- 1999-12-03 MY MYPI99005261A patent/MY122401A/en unknown
- 1999-12-06 AR ARP990106207A patent/AR023718A1/es active IP Right Grant
- 1999-12-06 CO CO99076401A patent/CO5121084A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2255323T3 (es) | 2006-06-16 |
| MY122401A (en) | 2006-04-29 |
| ATE318280T1 (de) | 2006-03-15 |
| CO5121084A1 (es) | 2002-01-30 |
| JP2002531655A (ja) | 2002-09-24 |
| CN100368462C (zh) | 2008-02-13 |
| CA2352053A1 (en) | 2000-06-15 |
| JP4459447B2 (ja) | 2010-04-28 |
| BR9915936A (pt) | 2001-08-21 |
| US6162877A (en) | 2000-12-19 |
| EP1135428B1 (en) | 2006-02-22 |
| EP1135428A1 (en) | 2001-09-26 |
| CN1329632A (zh) | 2002-01-02 |
| ID29033A (id) | 2001-07-26 |
| AU1833500A (en) | 2000-06-26 |
| DE69930003D1 (de) | 2006-04-27 |
| WO2000034361A1 (en) | 2000-06-15 |
| AR023718A1 (es) | 2002-09-04 |
| TW580506B (en) | 2004-03-21 |
| DE69930003T2 (de) | 2006-10-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2352053C (en) | Hydrophobically modified comb copolymers | |
| CA2221748C (en) | Associative thickeners | |
| CN101298514B (zh) | 增稠剂组合物和对水性体系增稠的方法 | |
| US4426485A (en) | Polymers with hydrophobe bunches | |
| AU2004233555B2 (en) | Nonionic associative thickener containing condensation polymer backbone | |
| EP1038892B1 (en) | Method of improving viscosity stability of aqueous compounds | |
| US20100069536A1 (en) | Process for tailoring water-borne coating compositions | |
| CN101676342A (zh) | 增稠的组合物和使水性聚合物组合物增稠的方法 | |
| CN1035879C (zh) | 聚氨酯、其用途以及含有该聚氨酯的水性涂料 | |
| AU2011291574B2 (en) | Viscosity regulating composition | |
| RU2388775C2 (ru) | Синтетический загуститель для краски, совместимый с красителем | |
| CA1179096A (en) | Urethane rheology modifiers substantially free of terminal hydrophobic groups and compositions containing same | |
| TW580508B (en) | Fine particle size low bulk density thermoplastic polymers | |
| CA2162899C (en) | Polymeric thickeners for aqueous compositions | |
| MXPA01005442A (en) | Hydrophobically modified comb copolymers | |
| MXPA97008482A (en) | Asociati thickeners | |
| KR20160051752A (ko) | Ici 증점제 조성물 및 용도 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20191125 |