JP2016503092A - 界面活性剤との高い相溶性を有する分散剤コポリマー - Google Patents
界面活性剤との高い相溶性を有する分散剤コポリマー Download PDFInfo
- Publication number
- JP2016503092A JP2016503092A JP2015549432A JP2015549432A JP2016503092A JP 2016503092 A JP2016503092 A JP 2016503092A JP 2015549432 A JP2015549432 A JP 2015549432A JP 2015549432 A JP2015549432 A JP 2015549432A JP 2016503092 A JP2016503092 A JP 2016503092A
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- Prior art keywords
- hydrogen
- weight
- methyl
- monomer
- residue
- Prior art date
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Links
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 22
- 239000004094 surface-active agent Substances 0.000 title claims description 12
- 229920001577 copolymer Polymers 0.000 title description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 85
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 85
- 239000000178 monomer Substances 0.000 claims abstract description 73
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 55
- 229920000642 polymer Polymers 0.000 claims abstract description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 8
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 8
- 239000011734 sodium Chemical group 0.000 claims abstract description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 6
- 239000011591 potassium Chemical group 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 238000006116 polymerization reaction Methods 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 24
- 239000003999 initiator Substances 0.000 claims description 15
- 229920005862 polyol Polymers 0.000 claims description 14
- 150000003077 polyols Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 9
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 9
- 238000004140 cleaning Methods 0.000 claims description 5
- 239000011877 solvent mixture Substances 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 25
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 21
- 229940079593 drug Drugs 0.000 description 21
- 239000003814 drug Substances 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- 239000003599 detergent Substances 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000008367 deionised water Substances 0.000 description 12
- 229910021641 deionized water Inorganic materials 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 11
- 239000004744 fabric Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 7
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 229920002125 Sokalan® Polymers 0.000 description 5
- -1 acryl Chemical group 0.000 description 5
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000003945 anionic surfactant Substances 0.000 description 4
- 239000012986 chain transfer agent Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000012423 maintenance Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000010408 sweeping Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000000502 dialysis Methods 0.000 description 3
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 3
- 238000004108 freeze drying Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 239000004584 polyacrylic acid Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 210000002374 sebum Anatomy 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- UXYMHGCNVRUGNO-UHFFFAOYSA-N 1-hydroxypropan-2-yl prop-2-enoate Chemical compound OCC(C)OC(=O)C=C UXYMHGCNVRUGNO-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 101100352919 Caenorhabditis elegans ppm-2 gene Proteins 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-isoascorbic acid Chemical compound OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 1
- 239000004262 Ethyl gallate Substances 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
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- 238000004458 analytical method Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- KHAYCTOSKLIHEP-UHFFFAOYSA-N docosyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC(=O)C=C KHAYCTOSKLIHEP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000010350 erythorbic acid Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 229940026239 isoascorbic acid Drugs 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
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- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 238000001208 nuclear magnetic resonance pulse sequence Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 229940048842 sodium xylenesulfonate Drugs 0.000 description 1
- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
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- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3757—(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions
-
- 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
- C08F2/04—Polymerisation in solution
- C08F2/06—Organic solvent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
Description
(b)1〜20重量%のモノマー(B)の重合残基であって、
乾燥した透析ポリマーのおよそ300mgをDMSO−d6の700μL中で溶解し、得られた溶液を5mmのNMR管へ移した。NMRスペクトルをBruker AVANCE300分光計を使用して得た。定量13Cスペクトルを8秒の回収遅延を使用して、zgig30パルス系列とともに取得した。
透析をMilliporeの500g/molの分離膜を備えたAmiconからの撹拌された200mLの限外濾過細胞を使用して実行した。脱イオン水を細胞に添加し、撹拌し、約10gのポリマー溶液を添加した。ポリマーが、完全に混ぜ合わされたとき、細胞が閉鎖され、撹拌を維持し、窒素ガスを毎平方インチ最高70ポンドの圧力になるまで細胞に直接的に適用した。細胞内容物を50mLまで濃縮した後、圧力を放出し、細胞を脱イオン水で補充し、再度濃縮した。その後、これを再度繰り返し、透析物が最終的に約25mLになるまで濃縮した。透析物を次に凍結乾燥させ、固形材料を回収した。
略記:
AA:アクリル酸
HPA:ヒドロキシプロピルアクリレート(異性体の混合物)
PAA:ポリアクリル酸
SMA:ステアリルメタクリレート
SXS:キシレンスルホン酸ナトリウム
WI:白色度E313
共供給の添加のために、機械的撹拌器、加熱マントル、熱電対、冷却器、窒素吸気(複数可)が装置された2リットルの丸底フラスコを450gのプロピレングリコールで充たした。薬缶の内容物を、窒素を掃引しながら撹拌し、87±1℃に加熱した。一方で、186gの氷状のAAと14gのSMAとのモノマー溶液を完全に混ぜ合わせ、薬缶への添加のためにメスシリンダーに添加した。14gのルパーソル11(tert−ブチルペルオキシピバレート)の開始剤溶液を薬缶への添加のために注射器に添加した。
実施例1の方法をさらに大きな規模で75%繰り返した。この材料を500Daの分離膜を使用して水中で透析し、より高いMW分率が真空中で凍結乾燥によって低減され、半固形になった。透析物のNMR分析は、79重量%のアクリル酸、9重量%のHPA、および13重量%のSMAを供した。
共供給の添加のために、機械的撹拌器、加熱マントル、熱電対、冷却器、窒素吸気(複数可)が装置された2リットルの丸底フラスコを450gのプロピレングリコールで充たした。薬缶の内容物を、窒素を掃引しながら撹拌し、96±1℃に加熱した。一方で、186gの氷状のAAと14gのSMAとのモノマー溶液を完全に混ぜ合わせ、薬缶への添加のためにメスシリンダーに添加した。25gの脱イオン水中に溶解された14gの過硫酸ナトリウムの開始剤溶液を調製し、薬缶への添加のために注射器に添加した。
実施例#2を以下の例外を用いて繰り返した。プロピレングリコール(900g)で薬缶を充たした。400gの氷状のAAのモノマー溶液を薬缶への添加のためにシリンダーに添加した。28gの過硫酸ナトリウムおよび50gの脱イオン水の開始剤溶液を調製した。2gの過硫酸ナトリウムおよび8gの脱イオン水のチェーサー溶液を調製した。
共供給の添加のために、機械的撹拌器、加熱マントル、熱電対、冷却器、窒素吸気(複数可)が装置された2リットルの丸底フラスコを475gのプロピレングリコールで充たした。薬缶の内容物を、窒素を掃引しながら撹拌し、82±1℃に加熱した。一方で、280gの氷状のAAと70gのブチルアクリレートとのモノマー溶液を完全に混ぜ合わせ、薬缶への添加のためにメスシリンダーに添加した。14gのルパーソル11(tert−ブチルペルオキシピバレート)の開始剤溶液を薬缶への添加のために注射器に添加した。21gの1−ドデカンチオールの連鎖制御因子溶液を薬缶への添加のために注射器に添加した。
共供給の添加ために、機械的撹拌機、加熱マントル、熱電対、冷却器、窒素吸気(複数可)が装置された2リットルの丸底フラスコを250gの脱イオン水、30gの50%のCAVASOL W7 M TL(Wacker Fine Chemicals)で充たした。9.15gの0.15%硫酸鉄7水和物の促進溶液を調製し、おいて置いた。12.75gの脱イオンに溶解された2gのメタ重亜硫酸ナトリウムの薬缶の添加剤を調製し、おいて置いた。薬缶の内容物を、窒素を掃引しながら撹拌し、78±1℃に加熱した。同時に、415gの氷状のAAと50gのヒドロキシプロピルアクリレートと35gのラウリルメタクリレートとのモノマー溶液を完全に混ぜ合わせ、薬缶への添加のためにメスシリンダーに添加した。25.5gの脱イオン水中に溶解された1.57gの過硫酸ナトリウムの開始剤溶液を薬缶への添加のために注射器に添加した。82.5gの脱イオン廃棄物中に溶解された38gのメタ重亜硫酸ナトリウム連鎖制御因子溶液を薬缶への添加のために注射器に添加した。
実施例2の方法を、反応温度を88±1℃に維持するという変更をして、繰り返した。完成生成物は、38.1%の固形内容物および7550cPsの完成粘度を有する。AAの残余内容物は、2077ppmであった。重量および数平均分子量は、それぞれ9404および1959g/molであった。この材料を500Daの分離膜を使用して水中で透析し、より高いMW分率が真空中で凍結乾燥によって低減され、半固形になった。透析物のNMR分析は、68重量%のアクリル酸、21重量%のHPA、および9重量%のSMAを供した。
Claims (11)
- (a)50〜95重量%のモノマー(A)の重合残基であって、
(b)1〜20重量%のモノマー(B)の重合残基であって、
(c)3〜30重量%のモノマー(C)の重合残基であって、
- R1が水素、メチル、またはCOOXであり、R2およびR3が独立して、水素またはメチルであり、R4、R5、およびR6が独立して、水素またはメチルであり、R7がC12−C30アルキルまたはC12−C30アラルキルであり、R8およびR9が水素であり、R10が水素またはメチルであり、R11およびR12が独立して、水素、C1−C4アルキル、またはヒドロキシメチルであり、nが1または2である、請求項1に記載のポリマー分散剤。
- 55〜90重量%のモノマー(A)の重合残基、4〜18重量%のモノマー(B)の重合残基、および5〜30重量%のモノマー(C)の重合残基を有する請求項2に記載のポリマー分散剤。
- 1,200〜4,000のMnを有する、請求項3に記載のポリマー分散剤。
- R1およびR2が水素であり、R3が水素またはメチルであり、R4およびR5が水素であり、R6が水素またはメチルであり、R7がC16−C22アルキルであり、R8およびR9が水素であり、R10が水素またはメチルであり、R11およびR12が独立して、水素、メチル、またはヒドロキシメチルである、請求項4に記載のポリマー分散剤。
- 前記ポリマー分散剤が、60〜85重量%のモノマー(A)の重合残基、6〜15重量%のモノマー(B)の重合残基、および6〜25重量%のモノマー(C)の重合残基を有する、請求項5に記載のポリマー分散剤。
- (a)50〜95重量%のモノマー(A)の重合残基であって、
(b)1〜20重量%のモノマー(B)の重合残基であって、
(c)3〜30重量%のモノマー(C)の重合残基であって、
有機ポリオールおよび水を含む溶媒混合物中で構造(A)のモノマーと構造(B)のモノマーとを合わせることを含み、前記有機ポリオールが式(I)を有し、
- R1が水素、メチル、またはCOOXであり、R2およびR3が独立して、水素またはメチルであり、R4、R5、およびR6が独立して、水素またはメチルであり、R7がC12−C30アルキルまたはC12−C30アラルキルであり、R8およびR9が独立して、水素またはメチルであり、R10が水素またはメチルであり、R11およびR12が独立して、水素、C1−C4アルキル、またはヒドロキシメチルであり、R13およびR14が独立して、水素、C1−C4アルキル、またはヒドロキシメチルであり、nが1または2であり、前記ポリマー分散剤が、55〜90重量%のモノマー(A)の重合残基、4〜18重量%のモノマー(B)の重合残基、および5〜30重量%のモノマー(C)の重合残基を有する、請求項7に記載の方法。
- モノマーおよび遊離ラジカル開始剤が、1〜6時間にわたって撹拌反応器内で前記溶媒混合物に供給され、前記反応器内容物の温度が50〜130℃に維持され、水と有機ポリオールとの比率が1:6〜1:100である、請求項8に記載の方法。
- R1およびR2が水素であり、R3が水素またはメチルであり、R4およびR5が水素であり、R6が水素またはメチルであり、R7がC16−C22アルキルであり、R8およびR9が水素であり、R10が水素またはメチルであり、R11およびR12が独立して、水素、メチル、またはヒドロキシメチルであり、R13およびR14が独立して、水素、メチル、またはヒドロキシメチルであり、前記ポリマー分散剤が、60〜85重量%のモノマー(A)の重合残基、6〜15重量%のモノマー(B)の重合残基、および6〜25重量%のモノマー(C)の重合残基を有する、請求項9に記載の方法。
- 洗浄剤組成物であって、
(a)10〜55重量%の界面活性剤と、
(b)40〜80重量%の水と、
(c)0.4〜10重量%のポリマー分散剤と、を含み、前記ポリマー分散剤が、
(i)50〜95重量%のモノマー(A)の重合残基であって、
(ii)1〜20重量%のモノマー(B)の重合残基であって、
(iii)3〜30重量%のモノマー(C)の重合残基であって、
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US20060094636A1 (en) | 2004-11-01 | 2006-05-04 | National Starch And Chemical Investment Holding Corp. | Hydrophobically modified polymers |
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GB1028446A (en) * | 1964-01-30 | 1966-05-04 | Shell Int Research | Polymeric compounds having free alcohol groups, and lubricants containing them |
JPS59501500A (ja) * | 1982-09-03 | 1984-08-23 | エル・ア−ル・シ−・プロダクツ・リミテツド | 浸漬ゴム製品 |
JPH09202894A (ja) * | 1995-10-27 | 1997-08-05 | Rohm & Haas Co | 自動食器洗い機用洗浄剤のためのポリカルボキシレート |
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