JP2011515527A - 燐含有ポリマー及び乳化剤を含むポリマー分散液 - Google Patents

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Publication number

JP2011515527A

JP2011515527A JP2011500238A JP2011500238A JP2011515527A JP 2011515527 A JP2011515527 A JP 2011515527A JP 2011500238 A JP2011500238 A JP 2011500238A JP 2011500238 A JP2011500238 A JP 2011500238A JP 2011515527 A JP2011515527 A JP 2011515527A

Authority

JP

Japan

Prior art keywords

polymer

monomer

meth

ethylenically unsaturated

esters

Prior art date

2008-03-20

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.)

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• 239000004815 dispersion polymer Substances 0.000 title claims abstract description 140
• 229920000642 polymer Polymers 0.000 title claims abstract description 92
• 239000003995 emulsifying agent Substances 0.000 title claims abstract description 38
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title description 6
• 229910052698 phosphorus Inorganic materials 0.000 title description 6
• 239000011574 phosphorus Substances 0.000 title description 6
• 239000000178 monomer Substances 0.000 claims abstract description 154
• 238000000576 coating method Methods 0.000 claims abstract description 97
• 239000003973 paint Substances 0.000 claims abstract description 85
• 239000011248 coating agent Substances 0.000 claims abstract description 62
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 58
• 238000007720 emulsion polymerization reaction Methods 0.000 claims abstract description 57
• 150000002148 esters Chemical class 0.000 claims abstract description 55
• 239000000049 pigment Substances 0.000 claims abstract description 49
• 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 29
• 150000001252 acrylic acid derivatives Chemical class 0.000 claims abstract description 26
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 26
• 238000005299 abrasion Methods 0.000 claims abstract description 20
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims abstract description 17
• 150000003839 salts Chemical class 0.000 claims abstract description 16
• 238000009826 distribution Methods 0.000 claims abstract description 14
• 150000002894 organic compounds Chemical class 0.000 claims abstract description 4
• -1 vinyl halides Chemical class 0.000 claims description 122
• 239000000203 mixture Substances 0.000 claims description 119
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 103
• HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 52
• 150000002763 monocarboxylic acids Chemical class 0.000 claims description 39
• 125000000217 alkyl group Chemical group 0.000 claims description 34
• 150000001875 compounds Chemical class 0.000 claims description 34
• 150000001991 dicarboxylic acids Chemical class 0.000 claims description 32
• 239000006185 dispersion Substances 0.000 claims description 30
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 229920002554 vinyl polymer Polymers 0.000 claims description 19
• XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 18
• 239000012855 volatile organic compound Substances 0.000 claims description 16
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 15
• 150000001408 amides Chemical class 0.000 claims description 12
• 150000001735 carboxylic acids Chemical class 0.000 claims description 11
• 150000001298 alcohols Chemical class 0.000 claims description 10
• 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 10
• 239000004721 Polyphenylene oxide Substances 0.000 claims description 9
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 9
• 229920000570 polyether Polymers 0.000 claims description 9
• IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims description 8
• XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
• 125000005529 alkyleneoxy group Chemical group 0.000 claims description 7
• 150000001414 amino alcohols Chemical class 0.000 claims description 7
• 150000003140 primary amides Chemical class 0.000 claims description 7
• 150000003460 sulfonic acids Chemical class 0.000 claims description 7
• 239000001023 inorganic pigment Substances 0.000 claims description 6
• 150000002825 nitriles Chemical class 0.000 claims description 6
• 150000003926 acrylamides Chemical class 0.000 claims description 4
• 150000008064 anhydrides Chemical class 0.000 claims description 4
• 239000012752 auxiliary agent Substances 0.000 claims description 4
• 150000004985 diamines Chemical class 0.000 claims description 4
• UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 4
• 239000011256 inorganic filler Substances 0.000 claims description 4
• 229910003475 inorganic filler Inorganic materials 0.000 claims description 4
• DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 claims description 4
• 229930195733 hydrocarbon Natural products 0.000 claims description 3
• 150000002430 hydrocarbons Chemical class 0.000 claims description 3
• 150000005673 monoalkenes Chemical class 0.000 claims description 3
• 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims description 2
• 150000002170 ethers Chemical class 0.000 claims description 2
• 150000004820 halides Chemical class 0.000 claims description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
• 229920006395 saturated elastomer Polymers 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical class [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
• 239000000463 material Substances 0.000 abstract description 76
• GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract 1
• 239000007864 aqueous solution Substances 0.000 description 134
• 238000006116 polymerization reaction Methods 0.000 description 85
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 71
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
• 239000000126 substance Substances 0.000 description 35
• 238000003756 stirring Methods 0.000 description 32
• 238000004519 manufacturing process Methods 0.000 description 31
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 30
• CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 30
• NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 22
• 235000011007 phosphoric acid Nutrition 0.000 description 22
• SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 21
• 239000000243 solution Substances 0.000 description 18
• CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 17
• VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 16
• CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 16
• 239000003431 cross linking reagent Substances 0.000 description 16
• 239000000945 filler Substances 0.000 description 16
• 239000003505 polymerization initiator Substances 0.000 description 16
• 229910021529 ammonia Inorganic materials 0.000 description 15
• FDENMIUNZYEPDD-UHFFFAOYSA-L disodium [2-[4-(10-methylundecyl)-2-sulfonatooxyphenoxy]phenyl] sulfate Chemical compound [Na+].[Na+].CC(C)CCCCCCCCCc1ccc(Oc2ccccc2OS([O-])(=O)=O)c(OS([O-])(=O)=O)c1 FDENMIUNZYEPDD-UHFFFAOYSA-L 0.000 description 14
• VSVCAMGKPRPGQR-UHFFFAOYSA-N propan-2-one;sulfurous acid Chemical compound CC(C)=O.OS(O)=O VSVCAMGKPRPGQR-UHFFFAOYSA-N 0.000 description 14
• 235000011121 sodium hydroxide Nutrition 0.000 description 14
• 239000007787 solid Substances 0.000 description 13
• 125000000524 functional group Chemical group 0.000 description 12
• 238000000034 method Methods 0.000 description 12
• 150000003254 radicals Chemical class 0.000 description 12
• 238000005201 scrubbing Methods 0.000 description 12
• 238000012360 testing method Methods 0.000 description 11
• OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 10
• 239000002245 particle Substances 0.000 description 10
• 229910052783 alkali metal Inorganic materials 0.000 description 9
• 238000004132 cross linking Methods 0.000 description 9
• 238000005259 measurement Methods 0.000 description 9
• 239000011734 sodium Substances 0.000 description 9
• 229910052708 sodium Inorganic materials 0.000 description 9
• 239000002562 thickening agent Substances 0.000 description 9
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 8
• 125000003172 aldehyde group Chemical group 0.000 description 8
• 239000003086 colorant Substances 0.000 description 8
• 150000005690 diesters Chemical class 0.000 description 8
• 125000000468 ketone group Chemical group 0.000 description 8
• 239000003607 modifier Substances 0.000 description 8
• CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
• 239000004793 Polystyrene Substances 0.000 description 7
• GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
• 238000006243 chemical reaction Methods 0.000 description 7
• ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 7
• 229910000366 copper(II) sulfate Inorganic materials 0.000 description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
• 239000001257 hydrogen Substances 0.000 description 7
• 229910052739 hydrogen Inorganic materials 0.000 description 7
• 239000004816 latex Substances 0.000 description 7
• 229920000126 latex Polymers 0.000 description 7
• FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
• 229920002223 polystyrene Polymers 0.000 description 7
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 7
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
• 239000002253 acid Substances 0.000 description 6
• 239000011230 binding agent Substances 0.000 description 6
• 125000004432 carbon atom Chemical group C* 0.000 description 6
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
• 238000002360 preparation method Methods 0.000 description 6
• 238000010526 radical polymerization reaction Methods 0.000 description 6
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
• 239000004094 surface-active agent Substances 0.000 description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
• 238000012644 addition polymerization Methods 0.000 description 5
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• 238000011109 contamination Methods 0.000 description 5
• 238000007046 ethoxylation reaction Methods 0.000 description 5
• YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical class O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 5
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• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 5
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• JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
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