JP4478649B2 - 微小球 - Google Patents
微小球 Download PDFInfo
- Publication number
- JP4478649B2 JP4478649B2 JP2005518462A JP2005518462A JP4478649B2 JP 4478649 B2 JP4478649 B2 JP 4478649B2 JP 2005518462 A JP2005518462 A JP 2005518462A JP 2005518462 A JP2005518462 A JP 2005518462A JP 4478649 B2 JP4478649 B2 JP 4478649B2
- Authority
- JP
- Japan
- Prior art keywords
- microspheres
- group
- sulfite
- methyl
- acrylonitrile
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000004005 microsphere Substances 0.000 title claims abstract description 83
- 239000000178 monomer Substances 0.000 claims abstract description 74
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 29
- 239000003380 propellant Substances 0.000 claims abstract description 23
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 claims abstract description 17
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 33
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 29
- 239000003814 drug Substances 0.000 claims description 19
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 18
- 239000006185 dispersion Substances 0.000 claims description 18
- 229940079593 drug Drugs 0.000 claims description 18
- -1 dithionate Chemical compound 0.000 claims description 17
- 229920000642 polymer Polymers 0.000 claims description 17
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- 239000002243 precursor Substances 0.000 claims description 17
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 16
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 16
- 229920000103 Expandable microsphere Polymers 0.000 claims description 14
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 10
- 229920005992 thermoplastic resin Polymers 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 150000002825 nitriles Chemical class 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 8
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 claims description 8
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims description 7
- 239000002002 slurry Substances 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 229920001519 homopolymer Polymers 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 5
- QAKHVURZPCJUQA-UHFFFAOYSA-N 2-cyanopropane-1-sulfonic acid Chemical compound N#CC(C)CS(O)(=O)=O QAKHVURZPCJUQA-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- VZZBCFHCABFUQL-UHFFFAOYSA-N 3-methoxy-2-methyl-3-oxopropane-1-sulfonic acid Chemical compound COC(=O)C(C)CS(O)(=O)=O VZZBCFHCABFUQL-UHFFFAOYSA-N 0.000 claims description 3
- YLKGJIWCQSXGTQ-UHFFFAOYSA-N 3-methoxy-3-oxopropane-1-sulfonic acid Chemical compound COC(=O)CCS(O)(=O)=O YLKGJIWCQSXGTQ-UHFFFAOYSA-N 0.000 claims description 3
- HRKQOINLCJTGBK-UHFFFAOYSA-L dioxidosulfate(2-) Chemical compound [O-]S[O-] HRKQOINLCJTGBK-UHFFFAOYSA-L 0.000 claims description 3
- 229940075933 dithionate Drugs 0.000 claims description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 3
- IEDUQDJAJCRCHF-UHFFFAOYSA-M 2-cyanoethanesulfonate Chemical compound [O-]S(=O)(=O)CCC#N IEDUQDJAJCRCHF-UHFFFAOYSA-M 0.000 claims description 2
- IEDUQDJAJCRCHF-UHFFFAOYSA-N 2-cyanoethanesulfonic acid Chemical compound OS(=O)(=O)CCC#N IEDUQDJAJCRCHF-UHFFFAOYSA-N 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- VYWNBUBFYLAECR-UHFFFAOYSA-N methyl 2-cyanoethanesulfonate Chemical compound COS(=O)(=O)CCC#N VYWNBUBFYLAECR-UHFFFAOYSA-N 0.000 claims description 2
- NVYIZOKWNVXEQJ-UHFFFAOYSA-N methyl 2-cyanopropane-1-sulfonate Chemical compound COS(=O)(=O)CC(C)C#N NVYIZOKWNVXEQJ-UHFFFAOYSA-N 0.000 claims description 2
- XDYJMYYWSYNYHH-UHFFFAOYSA-N methyl 3-methoxysulfonyl-2-methylpropanoate Chemical compound COC(=O)C(C)CS(=O)(=O)OC XDYJMYYWSYNYHH-UHFFFAOYSA-N 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims 4
- 238000003379 elimination reaction Methods 0.000 claims 4
- 230000007717 exclusion Effects 0.000 claims 2
- 159000000003 magnesium salts Chemical class 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 abstract description 10
- 239000003574 free electron Substances 0.000 abstract description 7
- 125000004434 sulfur atom Chemical group 0.000 abstract description 7
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 6
- 239000011593 sulfur Substances 0.000 abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 3
- 150000004715 keto acids Chemical class 0.000 abstract description 3
- 239000000463 material Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000005187 foaming Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 6
- 229940001584 sodium metabisulfite Drugs 0.000 description 6
- 235000010262 sodium metabisulphite Nutrition 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- 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 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000000375 suspending agent Substances 0.000 description 5
- 229920002725 thermoplastic elastomer Polymers 0.000 description 5
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 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
- 125000004386 diacrylate group Chemical group 0.000 description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- 238000002845 discoloration Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 4
- 239000000347 magnesium hydroxide Substances 0.000 description 4
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 239000004604 Blowing Agent Substances 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
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 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
- 239000003999 initiator Substances 0.000 description 3
- 239000001282 iso-butane Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 238000002310 reflectometry Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-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
- 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 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Natural products CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- GYGXGLJCAHRRLQ-UHFFFAOYSA-N 3-amino-3-oxopropane-1-sulfonic acid Chemical compound NC(=O)CCS(O)(=O)=O GYGXGLJCAHRRLQ-UHFFFAOYSA-N 0.000 description 2
- OURSFPZPOXNNKX-UHFFFAOYSA-N 3-sulfopropanoic acid Chemical compound OC(=O)CCS(O)(=O)=O OURSFPZPOXNNKX-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- QXDMQSPYEZFLGF-UHFFFAOYSA-L calcium oxalate Chemical compound [Ca+2].[O-]C(=O)C([O-])=O QXDMQSPYEZFLGF-UHFFFAOYSA-L 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000000451 gelidium spp. gum Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 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 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- IPJKJLXEVHOKSE-UHFFFAOYSA-L manganese dihydroxide Chemical compound [OH-].[OH-].[Mn+2] IPJKJLXEVHOKSE-UHFFFAOYSA-L 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
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 2
- 239000011087 paperboard Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000003672 processing method Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- CBYABTHXYJJUTO-UHFFFAOYSA-N (1-tert-butylcyclohexyl) carboxyoxy carbonate Chemical compound OC(=O)OOC(=O)OC1(C(C)(C)C)CCCCC1 CBYABTHXYJJUTO-UHFFFAOYSA-N 0.000 description 1
- LGPAKRMZNPYPMG-UHFFFAOYSA-N (3-hydroxy-2-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OC(CO)COC(=O)C=C LGPAKRMZNPYPMG-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
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AKUNSTOMHUXJOZ-UHFFFAOYSA-N 1-hydroperoxybutane Chemical compound CCCCOO AKUNSTOMHUXJOZ-UHFFFAOYSA-N 0.000 description 1
- LRZPQLZONWIQOJ-UHFFFAOYSA-N 10-(2-methylprop-2-enoyloxy)decyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCOC(=O)C(C)=C LRZPQLZONWIQOJ-UHFFFAOYSA-N 0.000 description 1
- RHNJVKIVSXGYBD-UHFFFAOYSA-N 10-prop-2-enoyloxydecyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCCOC(=O)C=C RHNJVKIVSXGYBD-UHFFFAOYSA-N 0.000 description 1
- DPGYCJUCJYUHTM-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-yloxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)CC(C)(C)C DPGYCJUCJYUHTM-UHFFFAOYSA-N 0.000 description 1
- JJBFVQSGPLGDNX-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)COC(=O)C(C)=C JJBFVQSGPLGDNX-UHFFFAOYSA-N 0.000 description 1
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 1
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- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/20—After-treatment of capsule walls, e.g. hardening
- B01J13/22—Coating
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C44/00—Shaping by internal pressure generated in the material, e.g. swelling or foaming ; Producing porous or cellular expanded plastics articles
- B29C44/34—Auxiliary operations
- B29C44/3461—Making or treating expandable particles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/22—After-treatment of expandable particles; Forming foamed products
- C08J9/228—Forming foamed products
- C08J9/232—Forming foamed products by sintering expandable particles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2300/00—Characterised by the use of unspecified polymers
- C08J2300/22—Thermoplastic resins
Description
式II
のいずれか一つに特定されたスルホン酸陰イオンの塩及び誘導体からなる群から選ばれた少なくとも一種の反応生成物を含む熱可塑性ポリマーシェルを含む発泡性熱可塑性樹脂微小球に関する。
Claims (18)
- 噴射剤をカプセル化し、更にアクリロニトリル、メタクリロニトリル及びメチルメタクリレートの少なくとも一種を含む残留モノマーを含む熱可塑性ポリマーシェルを含む微小球を、前記残留モノマーの少なくとも一部と直接又は間接に反応する薬剤と接触させる工程を含む発泡性熱可塑性樹脂微小球の製造方法であって、前記薬剤が重亜硫酸塩、スルファイト(亜硫酸塩、亜硫酸エステル)及び亜硫酸からなる群から選ばれることを特徴とする発泡性熱可塑性樹脂微小球の製造方法。
- 前記薬剤が重亜硫酸塩及びスルファイト(亜硫酸塩、亜硫酸エステル)からなる群から選ばれる、請求項1に記載の製造方法。
- 前記薬剤が、二酸化硫黄、塩化スルホニル、二亜硫酸塩、亜ジチオン酸塩、ジチオン酸塩、及びスルホキシレートからなる群より選択される前駆体から生成される、請求項1または2に記載の製造方法。
- 前記前駆体が二亜硫酸塩、亜ジチオン酸塩及び二酸化硫黄からなる群から選ばれる、請求項3に記載の製造方法。
- 前記発泡性微小球を残留モノマーと反応するための薬剤と接触させる工程中の発泡性微小球が、これらの微小球が製造された重合混合物に由来する水性スラリー又は分散液の形態である、請求項1から4のいずれか1項に記載の製造方法。
- 前記残留モノマーがアクリロニトリル及びメタクリロニトリルの少なくとも一種を含む、請求項1から5のいずれか1項に記載の製造方法。
- 前記発泡性微小球の熱可塑性ポリマーシェルが、ニトリル含有モノマーの合計量が少なくとも70重量%であるエチレン性不飽和モノマーを重合することにより得られたホモポリマー又はコポリマーからつくられる、請求項1から6のいずれか1項に記載の製造方法。
- 噴射剤をカプセル化し、更にアクリロニトリル、メタクリロニトリル及びメチルメタクリレートの少なくとも一種を含む残留モノマーを含む熱可塑性ポリマーシェルを含む熱可塑性樹脂発泡性微小球からの残留モノマーの排除又は低減方法であって、その方法が前記微小球を重亜硫酸塩、スルファイト(亜硫酸塩、亜硫酸エステル)及び亜硫酸からなる群から選ばれた薬剤と接触させる工程を含むことを特徴とする前記残留モノマーの排除又は低減方法。
- 前記薬剤が重亜硫酸塩及びスルファイト(亜硫酸塩、亜硫酸エステル)からなる群から選ばれる、請求項8に記載の排除又は低減方法。
- 前記薬剤が、二酸化硫黄、塩化スルホニル、二亜硫酸塩、亜ジチオン酸塩、ジチオン酸塩、及びスルホキシレートからなる群より選択される前駆体から生成される、請求項8または9に記載の排除又は低減方法。
- 前記前駆体が二亜硫酸塩、亜ジチオン酸塩及び二酸化硫黄からなる群から選ばれる、請求項10に記載の排除又は低減方法。
- 前記発泡性微小球を残留モノマーと反応するための薬剤と接触させる工程中の発泡性微小球が、これらの微小球が製造された重合混合物に由来する水性スラリー又は分散液の形態である、請求項8から11のいずれか1項に記載の排除又は低減方法。
- 前記残留モノマーがアクリロニトリル及びメタクリロニトリルの少なくとも一種を含む、請求項8から12のいずれか1項に記載の排除又は低減方法。
- 前記発泡性微小球の熱可塑性ポリマーシェルが、ニトリル含有モノマーの合計量が少なくとも70重量%であるエチレン性不飽和モノマーを重合することにより得られたホモポリマー又はコポリマーからつくられる、請求項8から13のいずれか1項に記載の排除又は低減方法。
- 請求項1から7のいずれか1項に記載の方法により得られる発泡性熱可塑性樹脂微小球。
- 噴射剤をカプセル化し、更にポリマーシェルのためのモノマーとして使用されるアクリロニトリル、メタクリロニトリル及びメチルメタクリレートの少なくとも一種と、重亜硫酸塩、スルファイト(亜硫酸塩、亜硫酸エステル)及び亜硫酸からなる群から選ばれる薬剤との少なくとも一種の非ポリマー反応生成物を含む熱可塑性ポリマーシェルを含むことを特徴とする発泡性熱可塑性樹脂微小球。
- 前記少なくとも一種の非ポリマー反応生成物が式I:
式II
のいずれか一つにより特定されたスルホン酸陰イオンの塩及び誘導体からなる群から選ばれる、請求項16に記載の発泡性熱可塑性樹脂微小球。 - 前記のスルホン酸陰イオンの塩又は誘導体が、2-シアノ-エタンスルホン酸、2-シアノ-2-メチル-エタンスルホン酸、2-メトキシカルボニル-エタンスルホン酸、2-メトキシカルボニル-2-メチル-エタンスルホン酸、2-シアノ-エタンスルホン酸メチルエステル、2-シアノ-2-メチル-エタンスルホン酸メチルエステル、2-メトキシカルボニル-2-メチル-エタンスルホン酸メチルエステル;並びに2-シアノ-エタンスルホネート、2-シアノ-2-メチル-エタンスルホネート及び2-メトキシカルボニル-2-メチル-エタンスルホネートのいずれか一つのナトリウム塩、カリウム塩、マグネシウム塩及びアンモニウム塩からなる群から選ばれる、請求項17に記載の発泡性熱可塑性樹脂微小球。
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PCT/SE2004/000031 WO2004072160A1 (en) | 2003-02-11 | 2004-01-14 | Microspheres |
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KR (1) | KR100647388B1 (ja) |
CN (1) | CN100354346C (ja) |
AT (1) | ATE435885T1 (ja) |
DE (1) | DE602004021905D1 (ja) |
ES (1) | ES2328810T3 (ja) |
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US8388809B2 (en) | 2006-02-10 | 2013-03-05 | Akzo Nobel N.V. | Microspheres |
US7956096B2 (en) | 2006-02-10 | 2011-06-07 | Akzo Nobel N.V. | Microspheres |
EP2086757A1 (en) | 2006-12-01 | 2009-08-12 | Akzo Nobel N.V. | Packaging laminate |
EP2297398B1 (en) | 2008-06-17 | 2013-09-25 | Akzo Nobel N.V. | Cellulosic product |
WO2010072663A1 (en) | 2008-12-22 | 2010-07-01 | Akzo Nobel N.V. | Microspheres |
DE102009016404A1 (de) | 2009-04-07 | 2010-10-21 | Evonik Stockhausen Gmbh | Verwendung von Hohlkörpern zur Herstellung wasserabsorbierender Polymergebilde |
WO2011091228A1 (en) | 2010-01-22 | 2011-07-28 | Dsm Ip Assets B.V. | Liquid radiation curable resins capable of curing into layers with selective visual effects and methods for the use thereof |
CN102477166A (zh) * | 2011-09-28 | 2012-05-30 | 深圳光启高等理工研究院 | 一种超材料基板及其制备方法 |
EP2841246B1 (en) | 2012-04-27 | 2016-07-27 | Compagnie Gervais Danone | Article comprising foamed polylactic acid and process of making the same |
EP2855007A2 (en) | 2012-05-30 | 2015-04-08 | Akzo Nobel Chemicals International B.V. | Microspheres |
EP2671716A1 (en) | 2012-06-08 | 2013-12-11 | Hexcel Composites SASU | Low density composite materials, their production and use |
ES2602909T3 (es) | 2012-09-07 | 2017-02-22 | Akzo Nobel Chemicals International B.V. | Método y dispositivo para la preparación de microesferas termoplásticas expandidas |
CN104072880B (zh) * | 2013-03-28 | 2016-09-28 | 晋江凯基高分子材料有限公司 | 一种tpo发泡微球的制备方法以及应用 |
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RU2640531C2 (ru) | 2013-06-12 | 2018-01-09 | Сикпа Холдинг Са | Термочувствительные метки для выявления фальсификации |
WO2016091847A1 (en) | 2014-12-11 | 2016-06-16 | Akzo Nobel Chemicals International B.V. | Apparatus and method for expanding thermally expandable thermoplastic microspheres to expanded thermoplastic microspheres |
DE16882443T1 (de) * | 2015-12-31 | 2019-05-02 | Polymer Adhesive Sealant Systems, Inc. | System und verfahren für flexibles dichtmittel mit dichtemodifizierungsmittel |
JP6774547B2 (ja) | 2016-07-14 | 2020-10-28 | ヌーリオン ケミカルズ インターナショナル ベスローテン フェノーツハップNouryon Chemicals International B.V. | 熱膨張性熱可塑性マイクロスフェアおよびそれらの調製方法 |
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CN106967195A (zh) * | 2017-04-18 | 2017-07-21 | 安徽联合辐化有限公司 | 一种通过γ射线辐照工艺提高收率的热膨胀微球的制备方法 |
JP2018188563A (ja) | 2017-05-09 | 2018-11-29 | 株式会社ダイセル | 絶縁膜形成用組成物、絶縁膜、及び絶縁膜を備えた半導体デバイス |
CN111194239B (zh) * | 2017-09-04 | 2021-09-21 | 诺力昂化学品国际有限公司 | 由生物基单体制成的热膨胀性微球 |
US11208538B2 (en) | 2017-11-21 | 2021-12-28 | Nouryon Chemicals International B.V. | Thermally expandable microspheres prepared from bio-based monomers |
KR20210016340A (ko) | 2018-04-05 | 2021-02-15 | 누리온 케미칼즈 인터내셔널 비.브이. | 팽창된 미세구를 제조하기 위한 장치 |
EP3628710A1 (en) | 2018-09-26 | 2020-04-01 | Holland Novochem Technical Coatings B.V. | Coating composition |
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CN100354346C (zh) | 2007-12-12 |
CN1738853A (zh) | 2006-02-22 |
EP1592733A1 (en) | 2005-11-09 |
ATE435885T1 (de) | 2009-07-15 |
DE602004021905D1 (de) | 2009-08-20 |
JP2006517240A (ja) | 2006-07-20 |
ES2328810T3 (es) | 2009-11-18 |
KR100647388B1 (ko) | 2006-11-23 |
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