JP6043427B2 - 微小球体 - Google Patents
微小球体 Download PDFInfo
- Publication number
- JP6043427B2 JP6043427B2 JP2015514440A JP2015514440A JP6043427B2 JP 6043427 B2 JP6043427 B2 JP 6043427B2 JP 2015514440 A JP2015514440 A JP 2015514440A JP 2015514440 A JP2015514440 A JP 2015514440A JP 6043427 B2 JP6043427 B2 JP 6043427B2
- Authority
- JP
- Japan
- Prior art keywords
- ethylenically unsaturated
- unsaturated monomer
- methacrylamide
- microsphere
- methacrylonitrile
- 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.)
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- 239000004005 microsphere Substances 0.000 title claims description 69
- 239000000178 monomer Substances 0.000 claims description 78
- 239000007788 liquid Substances 0.000 claims description 45
- 239000004604 Blowing Agent Substances 0.000 claims description 39
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 37
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 36
- 229920000103 Expandable microsphere Polymers 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 22
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 20
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 16
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 16
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 16
- 229920001169 thermoplastic Polymers 0.000 claims description 15
- SGVYKUFIHHTIFL-UHFFFAOYSA-N Isobutylhexyl Natural products CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 claims description 11
- 238000009472 formulation Methods 0.000 claims description 11
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 claims description 9
- 239000004088 foaming agent Substances 0.000 claims description 9
- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 150000002430 hydrocarbons Chemical class 0.000 claims description 7
- 239000011159 matrix material Substances 0.000 claims description 6
- 238000001125 extrusion Methods 0.000 claims description 5
- 238000001746 injection moulding Methods 0.000 claims description 5
- 239000001282 iso-butane Substances 0.000 claims description 5
- 239000004416 thermosoftening plastic Substances 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 24
- 238000006116 polymerization reaction Methods 0.000 description 15
- -1 carboxylic acid compounds Chemical class 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- 239000000375 suspending agent Substances 0.000 description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 150000004679 hydroxides Chemical class 0.000 description 3
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 3
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 3
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 3
- 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 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 229910052748 manganese Inorganic materials 0.000 description 3
- 239000011572 manganese Substances 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 2
- FYBFGAFWCBMEDG-UHFFFAOYSA-N 1-[3,5-di(prop-2-enoyl)-1,3,5-triazinan-1-yl]prop-2-en-1-one Chemical compound C=CC(=O)N1CN(C(=O)C=C)CN(C(=O)C=C)C1 FYBFGAFWCBMEDG-UHFFFAOYSA-N 0.000 description 2
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Natural products CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 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 2
- 239000003999 initiator Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 238000002356 laser light scattering Methods 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 239000012815 thermoplastic material Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- GYYDPBCUIJTIBM-DYOGSRDZSA-N (2r,3s,4s,5r)-2-(hydroxymethyl)-6-[[(4r,5s)-4-hydroxy-3-methyl-2,6-dioxabicyclo[3.2.1]octan-8-yl]oxy]-4-methoxyoxane-3,5-diol Chemical compound O[C@@H]1[C@@H](OC)[C@@H](O)[C@@H](CO)OC1OC1[C@H]2OCC1OC(C)[C@H]2O GYYDPBCUIJTIBM-DYOGSRDZSA-N 0.000 description 1
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 1
- KYPOHTVBFVELTG-OWOJBTEDSA-N (e)-but-2-enedinitrile Chemical compound N#C\C=C\C#N KYPOHTVBFVELTG-OWOJBTEDSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical compound ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- RVBFWXYFXKDVKG-UHFFFAOYSA-N 2-ethoxyprop-2-enenitrile Chemical compound CCOC(=C)C#N RVBFWXYFXKDVKG-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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- C08J2333/24—Homopolymers or copolymers of amides or imides
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- C08J2433/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2433/18—Homopolymers or copolymers of nitriles
- C08J2433/22—Homopolymers or copolymers of nitriles containing four or more carbon atoms
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Landscapes
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- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
Mg(OH)2により安定化された有機液滴を水に含有する反応混合物を、これらの相を混合し、好適な液滴サイズが達成されるまで激しく撹拌することによって調製した。この水分散物は4.9部のMg(OH)2及び370部の水を含有した。有機液滴は、2部のジラウロイルペルオキシド、25部のイソオクタン、50部のメタクリロニトリル、50部のメタクリルアミド及び0.4部のトリメチロールプロパントリメタクリラートを含有した。重合を、撹拌下、密封された反応器において、62℃で11時間行い、その後、80℃で4時間行った。室温に冷却した後、得られた微小球体スラリーのサンプルを、粒子サイズ分布を求めるために取り出した。ろ過、洗浄及び乾燥の後、粒子をTMAによって分析した。乾燥粒子は約31重量%のイソオクタンを含有し、メジアン粒子サイズが約51μmであった。TMAの結果が表1に見出される。
微小球体を、表1に従ってモノ官能性モノマー(すなわち、ただ1つの炭素・炭素間の二重結合を有するモノマー)をを添加したことを除いて、実施例1の場合のように行われる複数の重合実験において調製した。比較例2では重合を62℃で20時間行ったことを除いて、重合を実施例1に記載されるように行った。分析結果を表1に見出すことができる。
微小球体を、表2に従って液体発泡剤を添加したことを除いて、実施例1での場合のように行われる複数の重合実験において調製した。分析結果を表2に見出すことができる。
微小球体を、表3に従ってモノ官能性モノマーを添加したことを除いて、実施例1での場合のように行われる複数の重合実験において調製した。さらに、実施例21では、0.5部のトリメチロールプロパントリメタクリラートを使用した。重合を、重合が62℃で20時間行われた実施例21を除いて、実施例1に記載されるように行った。分析結果を表3に見出すことができる。
微小球体を、Mg(OH)2の代わりにシリカの水分散物を使用することによって有機液滴を安定化させながら、モノマー及び液体発泡剤を除いて実施例1での場合のように調製した。有機液滴は、0.8部のジラウロイルペルオキシド、13部のイソヘキサン、13部のイソオクタン、40部のアクリロニトリル、23部のメタクリロニトリル、30部のメタクリル酸、3.5部のメタクリルアミド、3.5部のスチレン及び0.2部のジエチレングリコールジメタクリラートからなった。水分散物を、244部の水、10部の1M NaOH、17部の10%酢酸、0.3部のCr(NO3)3、10部の40%コロイド状シリカ、0.9部の、ジエタノールアミンとアジピン酸との縮合生成物、1.5部のアスコルビン酸、及び7部のNa2SO4を混合することによって調製した。重合を70℃で20時間行った。分析結果を表4に見出すことができる。
有機液滴が54部のメタクリロニトリル、46部のメタクリル酸、30部のイソオクタン及び2.4部のジラウロイルペルオキシドからなることを除いて、微小球体を参考例29の場合のように調製した。重合を60℃で15時間行い、その後、70℃で9時間行った。分析結果を表4に見出すことができる。
微小球体を、モノマーが64部のメタクリロニトリル及び36部のメタクリル酸からなることを除いて、参考例30での場合のように調製した。分析結果を表4に見出すことができる。
表5において、メタクリロニトリル及びメタクリルアミドから得られるコポリマー外殻を有する本発明による微小球体(実施例1及び実施例9)が、先行技術による参考例(参考例29〜参考例31)と比較して、250℃で1時間加熱した後でさえ、優れた体積保持を有することを認めることができる。
[1]
液体発泡剤を封入させてエチレン性不飽和モノマーから調製されるポリマー外殻を含み、前記エチレン性不飽和モノマーが21wt%〜80wt%のメタクリルアミド及び20wt%〜70wt%のメタクリロニトリルを含み、メタクリルアミド及びメタクリロニトリルの総量が前記エチレン性不飽和モノマーの70wt%〜100wt%である熱膨張性の熱可塑性微小球体。
[2]
前記エチレン性不飽和モノマーが30wt%〜70wt%のメタクリルアミド及び30wt%〜60wt%のメタクリロニトリルを含む、[1]に記載の微小球体。
[3]
前記エチレン性不飽和モノマーが31wt%〜80wt%のメタクリルアミドを含む、[1]に記載の微小球体。
[4]
メタクリルアミド及びメタクリロニトリルの総量が前記エチレン性不飽和モノマーの80wt%〜100wt%である、[1]〜[3]のいずれかに記載の微小球体。
[5]
メタクリルアミド及びメタクリロニトリルの総量が前記エチレン性不飽和モノマーの90%〜100%である、[4]に記載の微小球体。
[6]
前記エチレン性不飽和モノマーが40wt%〜60wt%のメタクリルアミドを含む、[1]〜[5]のいずれかに記載の微小球体。
[7]
前記エチレン性不飽和モノマーが40wt%〜60wt%のメタクリロニトリルを含む、[1]〜[6]のいずれかに記載の微小球体。
[8]
前記エチレン性不飽和モノマーがカルボン酸含有モノマーを含まないか、又は、10wt%未満のカルボン酸含有モノマーを含む、[1]〜[7]のいずれかに記載の微小球体。
[9]
前記液体発泡剤が、イソブタン、イソペンタン、イソヘキサン、シクロヘキサン、イソオクタン、イソドデカン及びそれらの混合物から選択される炭化水素を含み、好ましくはイソオクタンを含む、[1]〜[8]のいずれかに記載の微小球体。
[10]
前記液体発泡剤が50wt%〜100wt%のイソオクタンを含む、[9]に記載の微小球体。
[11]
[1]〜[10]のいずれかに記載される熱膨張性微小球体を製造するための方法であって、エチレン性不飽和モノマーを液体発泡剤の存在下で重合して、前記液体発泡剤を封入するポリマー外殻を含む微小球体を生じさせることを含み、前記エチレン性不飽和モノマーが21wt%〜80wt%のメタクリルアミド及び20wt%〜70wt%のメタクリロニトリルを含み、メタクリルアミド及びメタクリロニトリルの総量が前記エチレン性不飽和モノマーの70wt%〜100wt%である、方法。
[12]
[1]〜[10]のいずれかに記載される膨張性微小球体を膨張させることによって得られる膨張させた微小球体。
[13]
熱可塑性ポリマーマトリックスと、[1]〜[10]のいずれかに記載される膨張性微小球体とを含む膨張性配合物。
[14]
[13]に記載される膨張性配合物を調製するための方法であって、熱可塑性ポリマーと、[1]〜[10]のいずれかに記載される膨張性微小球体とを、前記ポリマーの融点を超えるが、前記微小球体の膨張温度よりも低い温度において混合することを含む、方法。
[15]
[1]〜[10]のいずれかに記載される熱膨張性微小球体又は[13]に記載される膨張性配合物の、起泡剤としての使用。
[16]
[1]〜[10]のいずれかに記載される熱膨張性微小球体又は[13]に記載される膨張性配合物の、射出成形又は押出し成形における使用。
Claims (13)
- 液体発泡剤を封入する、エチレン性不飽和モノマーから調製されるポリマー外殻を含み、前記エチレン性不飽和モノマーが21重量%〜80重量%のメタクリルアミド及び20重量%〜70重量%のメタクリロニトリルを含み、メタクリルアミド及びメタクリロニトリルの総量が前記エチレン性不飽和モノマーの70重量%〜100重量%であり、
前記エチレン性不飽和モノマーが、カルボン酸含有モノマーを含まないか、又は、10重量%未満のカルボン酸含有モノマーを含む、熱膨張性の熱可塑性微小球体。 - 前記エチレン性不飽和モノマーが30重量%〜70重量%のメタクリルアミド及び30重量%〜60重量%のメタクリロニトリルを含む、請求項1に記載の微小球体。
- 前記エチレン性不飽和モノマーが31重量%〜80重量%のメタクリルアミドを含む、請求項1に記載の微小球体。
- メタクリルアミド及びメタクリロニトリルの総量が前記エチレン性不飽和モノマーの80重量%〜100重量%である、請求項1〜3のいずれか一項に記載の微小球体。
- メタクリルアミド及びメタクリロニトリルの総量が前記エチレン性不飽和モノマーの90%〜100%である、請求項4に記載の微小球体。
- 前記エチレン性不飽和モノマーが40重量%〜60重量%のメタクリルアミドを含む、請求項1〜5のいずれか一項に記載の微小球体。
- 前記エチレン性不飽和モノマーが40重量%〜60重量%のメタクリロニトリルを含む、請求項1〜6のいずれか一項に記載の微小球体。
- 前記液体発泡剤が、イソブタン、イソペンタン、イソヘキサン、シクロヘキサン、イソオクタン、イソドデカン及びそれらの混合物から選択される炭化水素を含む、請求項1〜7のいずれか一項に記載の微小球体。
- 前記液体発泡剤が50重量%〜100重量%のイソオクタンを含む、請求項8に記載の微小球体。
- 請求項1〜9のいずれか一項に記載される熱膨張性微小球体を製造するための方法であって、エチレン性不飽和モノマーを液体発泡剤の存在下で重合して、前記液体発泡剤を封入するポリマー外殻を含む微小球体を生じさせることを含み、前記エチレン性不飽和モノマーが21重量%〜80重量%のメタクリルアミド及び20重量%〜70重量%のメタクリロニトリルを含み、メタクリルアミド及びメタクリロニトリルの総量が前記エチレン性不飽和モノマーの70重量%〜100重量%である、方法。
- 熱可塑性ポリマーマトリックスと、請求項1〜9のいずれか一項に記載される膨張性微小球体とを含む膨張性配合物。
- 請求項1〜9のいずれか一項に記載される熱膨張性微小球体又は請求項11に記載される膨張性配合物の、起泡剤としての使用。
- 請求項1〜9のいずれか一項に記載される熱膨張性微小球体又は請求項11に記載される膨張性配合物の、射出成形又は押出し成形における使用。
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US7956096B2 (en) * | 2006-02-10 | 2011-06-07 | Akzo Nobel N.V. | Microspheres |
BRPI0707621A2 (pt) | 2006-02-10 | 2011-05-10 | Akzo Nobel Nv | microesferas |
US8388809B2 (en) * | 2006-02-10 | 2013-03-05 | Akzo Nobel N.V. | Microspheres |
EP1981630B1 (en) | 2006-02-10 | 2015-09-23 | Akzo Nobel N.V. | Microspheres |
US7794755B2 (en) * | 2006-04-11 | 2010-09-14 | E.I. Du Pont De Nemours And Company | Process for preparation of swellable and deformable microspheres |
US20070287776A1 (en) * | 2006-06-08 | 2007-12-13 | Akzo Nobel N.V. | Microspheres |
EP2026902B1 (en) | 2006-06-08 | 2016-09-07 | Akzo Nobel N.V. | Microspheres |
US20100180995A1 (en) | 2006-10-24 | 2010-07-22 | Hiroyuki Teratani | Heat-expandable microspheres and hollow fine particles and method for producing the same as well as tire/rim assembly |
CN101827911B (zh) * | 2007-10-16 | 2013-03-27 | 松本油脂制药株式会社 | 热膨胀性微球,其制备方法及其应用 |
JP5485611B2 (ja) | 2008-08-07 | 2014-05-07 | 積水化学工業株式会社 | 熱膨張性マイクロカプセル及び発泡成形体 |
WO2010038615A1 (ja) | 2008-09-30 | 2010-04-08 | 積水化学工業株式会社 | 発泡成形用マスターバッチ及び発泡成形体 |
EP2529830A3 (en) | 2009-06-09 | 2014-10-29 | Matsumoto Yushi-Seiyaku Co., Ltd. | Heat-expandable microspheres and a method of making heat-expandable microspheres and application thereof |
JP5534576B2 (ja) * | 2009-07-08 | 2014-07-02 | 株式会社クレハ | 熱膨張性マイクロスフェアー及びその製造方法、添加剤並びに成形体 |
JPWO2011013499A1 (ja) | 2009-07-28 | 2013-01-07 | 松本油脂製薬株式会社 | 発泡成形体の製造方法 |
JP5898953B2 (ja) * | 2010-03-31 | 2016-04-06 | 積水化学工業株式会社 | 熱膨張性マイクロカプセル及び熱膨張性マイクロカプセルの製造方法 |
CN102304200B (zh) * | 2011-05-27 | 2013-08-21 | 中国海洋石油总公司 | 一种交联聚合物微球及其制备方法 |
BR112014028746A2 (pt) | 2012-05-30 | 2017-06-27 | Akzo Nobel Chemicals Int Bv | microesferas termoplásticas termicamente expansíveis; processo de produção de microesferas termicamente expansíveis; microesferas expandidas; formulação expansível; processo de preparação de formulação expansível; e uso das microesferas termicamente expansíveis |
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2013
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- 2013-05-27 JP JP2015514440A patent/JP6043427B2/ja active Active
- 2013-05-27 WO PCT/EP2013/060818 patent/WO2013178561A2/en active Application Filing
- 2013-05-27 KR KR1020147032710A patent/KR102114784B1/ko active IP Right Grant
- 2013-05-27 US US14/402,958 patent/US9902829B2/en not_active Expired - Fee Related
- 2013-05-27 EP EP13725357.1A patent/EP2855007A2/en not_active Withdrawn
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WO2013178561A2 (en) | 2013-12-05 |
CN104334268A (zh) | 2015-02-04 |
CN104334268B (zh) | 2017-03-01 |
WO2013178561A3 (en) | 2014-01-30 |
KR20150024817A (ko) | 2015-03-09 |
KR102114784B1 (ko) | 2020-05-26 |
BR112014028746A2 (pt) | 2017-06-27 |
US9902829B2 (en) | 2018-02-27 |
JP2015523908A (ja) | 2015-08-20 |
US20150322226A1 (en) | 2015-11-12 |
EP2855007A2 (en) | 2015-04-08 |
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