JP2022503878A - ポリアミン添加剤 - Google Patents
ポリアミン添加剤 Download PDFInfo
- Publication number
- JP2022503878A JP2022503878A JP2021517483A JP2021517483A JP2022503878A JP 2022503878 A JP2022503878 A JP 2022503878A JP 2021517483 A JP2021517483 A JP 2021517483A JP 2021517483 A JP2021517483 A JP 2021517483A JP 2022503878 A JP2022503878 A JP 2022503878A
- Authority
- JP
- Japan
- Prior art keywords
- weight
- water
- group
- polyamine
- monomer
- 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.)
- Granted
Links
- 229920000768 polyamine Polymers 0.000 title claims abstract description 120
- 239000000654 additive Substances 0.000 title claims abstract description 112
- 230000000996 additive effect Effects 0.000 title claims description 72
- 239000000178 monomer Substances 0.000 claims abstract description 131
- 229920000642 polymer Polymers 0.000 claims abstract description 130
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 86
- 239000002270 dispersing agent Substances 0.000 claims abstract description 65
- 125000000129 anionic group Chemical group 0.000 claims abstract description 49
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims abstract description 22
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 13
- 239000012736 aqueous medium Substances 0.000 claims abstract description 9
- 238000000576 coating method Methods 0.000 claims description 92
- 239000011248 coating agent Substances 0.000 claims description 76
- 239000008199 coating composition Substances 0.000 claims description 67
- 229920001577 copolymer Polymers 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 20
- 125000002947 alkylene group Chemical group 0.000 claims description 20
- 230000000087 stabilizing effect Effects 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 239000000049 pigment Substances 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 239000000945 filler Substances 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- 150000003512 tertiary amines Chemical class 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- 239000004408 titanium dioxide Substances 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 5
- 229920001519 homopolymer Polymers 0.000 claims description 4
- 125000006539 C12 alkyl group Chemical group [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])* 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 2
- 238000007605 air drying Methods 0.000 claims 2
- 238000010526 radical polymerization reaction Methods 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 238000005259 measurement Methods 0.000 claims 1
- 235000020354 squash Nutrition 0.000 claims 1
- 238000001035 drying Methods 0.000 abstract description 24
- 125000001302 tertiary amino group Chemical group 0.000 abstract 1
- 239000010408 film Substances 0.000 description 57
- 239000000203 mixture Substances 0.000 description 52
- 238000006243 chemical reaction Methods 0.000 description 43
- 239000002245 particle Substances 0.000 description 41
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 29
- 239000002585 base Substances 0.000 description 25
- FLCAEMBIQVZWIF-UHFFFAOYSA-N 6-(dimethylamino)-2-methylhex-2-enamide Chemical compound CN(C)CCCC=C(C)C(N)=O FLCAEMBIQVZWIF-UHFFFAOYSA-N 0.000 description 23
- -1 more preferably H Chemical group 0.000 description 23
- 239000012071 phase Substances 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- 239000003999 initiator Substances 0.000 description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 17
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- 230000004888 barrier function Effects 0.000 description 14
- 230000002209 hydrophobic effect Effects 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
- 125000003277 amino group Chemical group 0.000 description 11
- 238000007720 emulsion polymerization reaction Methods 0.000 description 11
- 238000001704 evaporation Methods 0.000 description 11
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- 238000003860 storage Methods 0.000 description 10
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 8
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 229920001971 elastomer Polymers 0.000 description 8
- 239000000806 elastomer Substances 0.000 description 8
- 230000003993 interaction Effects 0.000 description 8
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-araboascorbic acid Natural products OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 7
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 235000010350 erythorbic acid Nutrition 0.000 description 7
- 239000004318 erythorbic acid Substances 0.000 description 7
- 229940026239 isoascorbic acid Drugs 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- IRLPACMLTUPBCL-KQYNXXCUSA-N 5'-adenylyl sulfate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O IRLPACMLTUPBCL-KQYNXXCUSA-N 0.000 description 6
- 102100026735 Coagulation factor VIII Human genes 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 6
- 230000002776 aggregation Effects 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 239000003139 biocide Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 229920000058 polyacrylate Polymers 0.000 description 6
- 229920001567 vinyl ester resin Polymers 0.000 description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 238000004220 aggregation Methods 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000003570 air Substances 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 210000002615 epidermis Anatomy 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229920006243 acrylic copolymer Polymers 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000010433 feldspar Substances 0.000 description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 3
- WVFLGSMUPMVNTQ-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-[[1-(2-hydroxyethylamino)-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCO WVFLGSMUPMVNTQ-UHFFFAOYSA-N 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
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- 239000002562 thickening agent Substances 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 2
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- 229940100555 2-methyl-4-isothiazolin-3-one Drugs 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
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- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
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- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
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- 150000001993 dienes Chemical class 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
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- 238000007046 ethoxylation reaction Methods 0.000 description 2
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- 125000000524 functional group Chemical group 0.000 description 2
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- 239000002609 medium Substances 0.000 description 2
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 2
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
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- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
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Classifications
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Abstract
Description
BASFによるUS2015/0259559は、アニオン性安定化コポリマー分散剤、揮発性塩基、およびアニオン性安定化コポリマー分散剤の硬化時間を短縮するように機能する誘導体化ポリアミンを含む組成物を開示している。
コーティング組成物は、金属、アスファルト、コンクリート、石、セラミック、木材、プラスチック、ポリマー、ポリウレタンフォーム、ガラス、およびそれらの組み合わせを含むがこれらに限定されない様々な表面に適用することができる。コーティング組成物は、内面または外面に塗布することができる。特定の実施形態では、表面は、屋根、壁、床、またはそれらの組み合わせなどの建築表面である。
DMAPMA - ジメチルアミノプロピルメタクリルアミド
HEMA - メタクリル酸2-ヒドロキシエチル
開始剤A - 4.8gの水に1.37gの70%TBHP
TBHP - t-ブチル過酸化水素
還元剤A - 24gの水に0.96gのエリソルビン酸
硫酸鉄(II)七水和物
Na4-ETDA - エチレンジアミン四酢酸四ナトリウム
AMPS(商標) 2045 - 2-アクリルアミド-2メチルプロパンスルホン酸またはそのナトリウム塩またはアンモニア塩(AMPS)
SLS - ラウリル硫酸ナトリウム
Bisomer(商標) MPEG 350MA - メタクリル酸でエステル化された350分子量のキャップ付きポリエチレンオキシド。Geoから入手可能。
メタクリルアミド
Sipomer PAM-100 - SolvayまたはRhodiaから入手可能なポリエチレングリコールメタクリレートのリン酸エステル
MMA - メタクリル酸メチル
2-EHA - 2-エチルヘキシルアクリレート
VCN アクリロニトリル
MAA - メタクリル酸
シランA-171 - ビニルトリメトキシシラン
COPS - Solvayから入手可能な1-アリルオキシ-2-ヒドロキシプロパンスルホネートナトリウム
スチレン
AA - アクリル酸
AE-960は、Lubrizol Advanced Materials, Inc.製の、アニオン性コロイド安定化基を有するアクリルポリマーである。Dow Rhoplex{1](商標)ED-1791、Rhoplex(商標)2885、またはBASF Acrynol(商標)NS 567などの同様のポリマーが使用可能であり、コーティングと同様の粘度と性能で同様の結果が得られる。
HEMAを使用した比較例I
モノマー組成=80 DMAPMA/20 HEMA。水性ポリマーを以下のように調製した。モノマープレミックスを、120gの水、96gのジメチルアミノプロピルメタクリルアミド(DMAPMA)、および24gの2-ヒドロキシルエチルアクリレート(HEMA)を混合することによって作成した。開始剤Aを、1.37gの70%t-ブチル過酸化水素(TBHP)を4.8gの水に混合して作成した。開始剤Aを、0.96gのエリソルビン酸を24gの水中に溶解することにより調製した。1リットルの反応容器に336gの水、1.68gの0.15%硫酸鉄(II)七水和物、および0.48gの1%エチレンジアミン四酢酸四ナトリウム(Na4-ETDA)を入れ、次いで適切に攪拌しながら窒素ブランケットの下で60℃に加熱した。60℃で、開始剤Aが反応容器に添加された。約2分後、モノマープレミックスが120分以上にわたって反応容器に分配し、還元剤Aが150分以上にわたって反応容器に分配した。還元剤Aの供給が完了した後、反応容器の温度を60℃で60分間維持した。次いで、反応容器を50℃に冷却した。6gの水中の0.43gの70%TBHPおよび0.04gの30%ラウリル硫酸ナトリウム(SLS)の溶液を反応容器に添加した。5分後、6gの水中の0.25gのエリソルビン酸の溶液を、反応容器に添加した。この反応容器を50℃に維持した。30分後、6gの水中の0.43gの70%TBHPおよび0.04gの30%ラウリル硫酸ナトリウム(SLS)の溶液を反応容器に添加した。5分後、6gの水中の0.25gのエリソルビン酸の溶液を、反応容器に添加した。この反応容器を約30分間、50℃に維持した。次いで、反応容器を室温まで冷却した。ポリマーのpHは9.5、固形分は16.4%、粘度は15cpsだった。
モノマー組成=80 DMAPMA/20 AMPS 2045。ポリマーは、HEMAの代わりに48gの50%AMPS 2405(Lubrizo製)を使用したことを除いて、比較例Iと同じように調製した。ポリマーのpHは10.9、固形分は17.6%、粘度は29cpsだった。
モノマー組成=80 DMAPMA/20 メタクリルアミド。ポリマーは、HEMAの代わりに24gのメタクリルアミドを使用したことを除いて、比較例Iと同じように調製した。ポリマーのpHは9.9、固形分は17.8%、粘度は24cpsだった。
ポリアミン添加剤の発明例
モノマー組成=80 DMAPMA/20 MPEG350 MA。ポリマーは、HEMAの代わりに24gのBisomer MPEG 350MA(GEO製)を使用したことを除いて、比較例Iと同じように調製した。ポリマーのpHは10.3、固形分は17.3%、粘度は31cpsだった。
モノマー組成=70 DMAPMA/30 MPEG350 MA。ポリマーは、84gのDMAPMAと36gのBisomer MPEG 350MAを含有する混合モノマーを使用したことを除いて、比較例Iと同じように調製した。ポリマーのpHは10.4、固形分は18.0%、粘度は11cpsだった。
モノマー組成=70 DMAPMA/30 MPEG1005 MA。エマルジョンポリマーを、以下のように調製した。モノマープレミックスを、153gの水、126gのジメチルアミノプロピルメタクリルアミド(DMAPMA)、および108gのVisiomer MEG 1005MA W(水中50%、Evonik製)を混合することによって作成した。開始剤Aを、0.9gの2,2’-アゾビス[2-メチル-N-(2-ヒドロキシエチル)プロピオンアミド](アゾVA-086、和光製)を14.4gの水中に溶解して作成した。開始剤Bを、0.27gのアゾVA-086を36gの水中に溶解することにより調製した。1リットルの反応容器に324gの水を入れ、次いで適切に攪拌しながら窒素ブランケットの下で85℃に加熱した。85℃で、開始剤Aが反応容器に添加され、次に、モノマープレミックスを75分間にわたって反応容器に分配した。モノマープレミックスの分配開始から約1分後に、開始剤Bを、120分間にわたって反応容器中に分配した。反応温度を、85℃に保った。開始剤Bの供給が完了した後、反応容器の温度を85℃で60分間維持した。次いで、反応容器を50℃に冷却した。9gの水中の0.64gの70%TBHPおよび0.06gの30%SLSの溶液を反応容器に添加した。5分後、9gの水中の0.38gのエリソルビン酸の溶液を、反応容器に添加した。この反応容器を50℃に維持した。30分後、9gの水中の0.64gの70%TBHPおよび0.06gの30%SLSの溶液を反応容器に添加した。5分後、9gの水中の0.38gのエリソルビン酸の溶液を、反応容器に添加した。この反応容器を約30分間、50℃に維持した。次いで、反応容器を室温まで冷却し、100ミクロンの布で濾過した。ポリマーのpHは10.1、固形分は22.4%、粘度は560cpsだった。
モノマー組成=70 DMAPMA/20 MPEG350 MA/10 PAM-100。ポリマーは、180gの水、18gのSipomer PAM-100(Solvay製)、8.4gの28%水酸化アンモニウム、126gのDMAPMA、および36gのBisomer MPEG 350MAを含有する混合モノマーを使用したことを除いて、実施例3と同じように調製した。ポリマーのpHは10.1、固形分は23.6%、粘度は1104cpsだった。
モノマー組成=70 DMAPMA/10 MPEG350 MA/20メタクリルアミド。エマルジョンポリマーを、以下のように調製した。モノマープレミックスを、160gの水、32gのメタクリルアミド、112gのジメチルアミノプロピルメタクリルアミド(DMAPMA)、および16gのBisomer MPEG 350MAを混合することによって作成した。開始剤Aを、0.8gの2,2’-アゾビス[2-メチル-N-(2-ヒドロキシエチル)プロピオンアミド](アゾVA-086、和光製)を20.5gの水中に溶解して作成した。開始剤Bを、0.24gのアゾVA-086を32gの水中に溶解することにより調製した。1リットルの反応容器に280gの水を入れ、次いで適切に攪拌しながら窒素ブランケットの下で85℃に加熱した。85℃で、開始剤Aが反応容器に添加され、次に、モノマープレミックスを75分間にわたって反応容器に分配した。モノマープレミックスの分配開始から約1分後に、開始剤Bを、120分間にわたって反応容器中に分配した。反応温度を、85℃に保った。開始剤Bの供給が完了した後、反応容器の温度を85℃で60分間維持した。次いで、反応容器を50℃に冷却した。8gの水中の0.57gの70%TBHPおよび0.05gの30%SLSの溶液を反応容器に添加した。5分後、8gの水中の0.34gのエリソルビン酸の溶液を、反応容器に添加した。この反応容器を50℃に維持した。30分後、8gの水中の0.57gの70%TBHPおよび0.05gの30%SLSの溶液を反応容器に添加した。5分後、8gの水中の0.34gのエリソルビン酸の溶液を、反応容器に添加した。この反応容器を約30分間、50℃に維持した。次いで、反応容器を室温まで冷却し、100ミクロンの布で濾過した。ポリマーのpHは10.3、固形分は22.34%、粘度は370cpsだった。
モノマー組成=70 DMAPMA/25 MPEG350 MA/5 AMPS-2411。ポリマーは、160gの水、16gのAMPS-2411(水中50%、Lubrizol製)、112gのDMAPMA、および40gのBisomer MPEG 350MAを含有する混合モノマーを使用したことを除いて、実施例5と同じように調製した。ポリマーのpHはpH10.0、固形分は22.94.0%、粘度は26cpsだった。
モノマー組成=85 DMAEMA/15 MPEG1005 MA。ポリマーは、180gの水、153gのジメチルアミノエチルメタクリレート(DMAEMA)、および54gのVisiomer MEG 1005MA Wを含有する混合モノマーを使用したことを除いて、実施例3と同じように調製した。ポリマーのpHはpH9.1、固形分は16.8%、粘度は990cpsだった。
モノマー組成=70 DMAEMA/20 MPEG350 MA/10MMA。ポリマーは、180gの水、126gのDMAEMA、18gのメチルメタクリレート(MMA)、および36gのBisomer MPEG 350MAを含有する混合モノマーを使用したことを除いて、実施例3と同じように調製した。ポリマーのpHは9.2、固形分は18.1%、粘度は8000cpsだった。
モノマー組成=50 DMAEMA/50 MPEG 350 MA。ポリマーは、180gの水、90gのDMAEMA、および90gのBisomer MPEG 350MAを含有する混合モノマーを使用したことを除いて、実施例3と同じように調製した。 ポリマーのpHは9.2、固形分は19.5%、粘度は1650cpsだった。
モノマー組成=80 DMAEMA/20 MPEG 350 MA。ポリマーは、128gの水、128gのDMAEMA、および64gのVisiomer MPEG 750MA-W(水中50%、Evonik製)を含有する混合モノマーを使用したことを除いて、実施例3と同じように調製した。ポリマーのpHは9.4、固形分は19.03%、粘度は576cpsだった。
モノマー組成=75 DMAEMA/15 MPEG 350 MA/10 n-VP。ポリマーは、180gの水、135gのDMAEMA、27gのBisomer MPEG 350MA、および18gのn-ビニルピロリジノンを含有する混合モノマーを使用したことを除いて、実施例3と同じように調製した。ポリマーのpHは9.3、固形分は16.6%、粘度は1280cpsだった。
モノマー組成=50 DMAPMA/50 MPEG350 MA。ポリマーは、60gのBisomer MPEG 350MAおよび60gのDMAPMAを使用したことを除いて、比較例Iと同じように調製した。ポリマーのpHは10.3、固形分は16.2%、粘度は10cpsだった。
モノマー組成=30 DMAPMA/70 MPEG350 MA。ポリマーは、84gのBisomer MPEG 350MAおよび36gのDMAPMAを使用したことを除いて、比較例Iと同じように調製した。ポリマーのpHは10.0、固形分は18.4%、粘度は40cpsだった。
安定性の調査では、ポリアミンを2倍の脱イオン水で希釈し、次に1重量%のポリアミンを適切な攪拌下で、固固ベースでポリマーに添加した。その後、50℃のオーブンで4週間熟成させる。結果を表IIIに要約する。
Claims (22)
- フリーラジカル重合性モノマーのポリアミンの繰り返し単位への重合生成物を含む水希釈性ポリアミン添加剤であって、
a) 30から90重量%の繰り返し単位は、式A1またはA2を含む群から選択されるフリーラジカル重合性第三級アミンモノマーからのものであり、
b) 10から60重量%の繰り返し単位は、以下の式のポリ(アルキレンオキシド)モノマーBからのものであり、
c) 約0から約60重量%の繰り返し単位は、モノマーA1、A2およびB以外の他のフリーラジカル重合性モノマーからのものである、水希釈性ポリアミン添加剤。 - 前記水希釈性ポリアミン添加剤の総重量に基づいて、A1およびA2からなる群から選択される前記第三級アミンモノマーからの繰り返し単位は、前記ポリアミン中に約55から85重量%存在し、前記繰り返し単位重合性アルキレンオキシドモノマーBは、約15から45重量%存在し、前記他のフリーラジカル重合性モノマーからの繰り返し単位は、0から30重量%存在する、請求項1に記載の水希釈性ポリアミン添加剤。
- 前記水希釈性ポリアミン添加剤の総重量に基づいて、A1またはA2から選択されるアミンモノマーからの繰り返し単位は、前記ポリアミン中に約60から80重量%存在し、前記繰り返し単位重合性アルキレンオキシドモノマーBは、約20から40重量%存在し、前記他のフリーラジカル重合性モノマーからの繰り返し単位は、0から15重量%存在する、請求項1に記載の水希釈性ポリアミン添加剤。
- 前記水希釈性ポリアミン添加剤の総重量に基づいて、前記他のフリーラジカル重合性モノマーからの繰り返し単位は、10重量%以下存在する、請求項1から3のいずれかに記載の水希釈性ポリアミン添加剤。
- ポリストリレン標準を使用するGPC分子量測定に基づいて、10,000から500,000ダルトンの数平均分子量を有する、請求項1から4のいずれかに記載の水希釈性ポリアミン添加剤。
- フリーラジカル重合性第三級アミンモノマーからの繰り返し単位は、A1およびA2から誘導された繰り返し単位の合計重量に基づいて、少なくとも80、90、または95重量%が、式A1を重合することから誘導された繰り返し単位である、請求項1から5のいずれかに記載の水希釈性ポリアミン添加剤。
- ReおよびRfの少なくとも90モル%はメチルまたはエチルである、請求項1から6のいずれかに記載の水希釈性ポリアミン添加剤。
- 前記Ra基の少なくとも80モル%はNRhである、請求項1から7のいずれかに記載の水希釈性ポリアミン添加剤。
- 前記Ra基の少なくとも80モル%はOである、請求項1から8のいずれかに記載の水希釈性ポリアミン添加剤。
- 水性媒体中のポリマー分散剤であって、
a) 10から75重量%の、水性媒体中のフリーラジカル重合モノマーのアニオン性コロイド状安定化コポリマー分散剤と、
b) 0.1から10重量%の水希釈性ポリアミン添加剤と、を含み、前記水希釈性ポリアミン添加剤は、
(1) 55から85重量%の、式A1およびA2からなる群から選択されるフリーラジカル重合性第三級アミンモノマーからの繰り返し単位と、
(2) 15から45重量%の、以下の式の重合性アルキレンオキシドモノマーBからの繰り返し単位と、
(3) 約0から約30重量%の、モノマーA1、A2およびB以外の他のフリーラジカル重合性モノマーと、のフリーラジカル重合生成物を含み、
ここで、前記ポリマー分散剤のpHは、7.5から12.5の間である、ポリマー分散剤。 - 前記コポリマーは、1から12個の炭素原子を有するアルカノールとの3から6個の炭素原子を有する3-モノエチレン性不飽和モノカルボン酸およびジカルボン酸のエステルである(メタ)アクリレートモノマーの重合から誘導された繰り返し単位を少なくとも50重量%含む、請求項10に記載のポリマー分散剤。
- 前記分散剤は、顔料または充填剤をさらに含む、請求項10または11のポリマー分散剤。
- A1およびA2からなる群の少なくとも80重量%が前記A1モノマーである、請求項10から12のいずれかに記載のポリマー分散剤。
- 前記コポリマーは、前記ポリマー分散剤の重量に基づいて、0.5から約2.5重量%の揮発性アミン(25℃で水よりも揮発性の高いアミンとして定義される)を含む、請求項10から13のいずれかに記載のポリマー分散剤。
- R2はメチルまたはエチルである、請求項10から14のいずれかに記載のポリマー分散剤。
- 不透明なコーティングを作製するために二酸化チタンと組み合わせて使用される、請求項10から15のいずれかに記載のポリマー分散剤。
- 屋根のコーティングとしての、請求項10から16のいずれかに記載のポリマー分散剤。
- 空気乾燥後の膜厚が10から100ミルである、請求項17に記載のポリマー分散剤。
- 空気乾燥後の膜厚が40ミル超である、請求項18に記載のポリマー分散剤。
- コーティング組成物に前記ポリアミン添加剤を含ませ、前記ポリアミンを前記コーティング組成物内で均質化することにより、前記コーティング組成物に早期の耐水性を付与するための請求項1から9のいずれかに記載の水希釈性ポリアミン添加剤の使用であって、前記コーティング組成物は、アニオン性安定化ポリマー分散剤を含む、使用。
- 前記ポリアミンが前記コーティング組成物に含まれる場合、前記コーティング組成物は9.5以上のpHを有する、請求項20に記載の水希釈性ポリアミン添加剤の使用。
- 基板上にフィルム状に形成されたコーティング組成物における耐水性の発現を高める方法であって、前記フィルムの形成前に前記コーティング組成物に請求項1から9のいずれかに記載の水希釈性ポリアミン添加剤を組み込むことを含み、このとき前記コーティング組成物は9.5以上のpHを有し、その後、前記コーティング組成物が基板上にフィルム状に形成されるまで、前記コーティング組成物のpHをpH9.5以上に維持し、基板上にフィルムを形成した後、前記コーティング組成物からの1つ以上のpH塩基性成分の揮発によって前記基板上の前記フィルムのpHを9未満に低下させることを含み、ここで、前記コーティング組成物は、アニオン性安定化ポリマー分散剤を含む、方法。
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