DE60025475T2 - Herstellung von polymerteilchen - Google Patents
Herstellung von polymerteilchen Download PDFInfo
- Publication number
- DE60025475T2 DE60025475T2 DE60025475T DE60025475T DE60025475T2 DE 60025475 T2 DE60025475 T2 DE 60025475T2 DE 60025475 T DE60025475 T DE 60025475T DE 60025475 T DE60025475 T DE 60025475T DE 60025475 T2 DE60025475 T2 DE 60025475T2
- Authority
- DE
- Germany
- Prior art keywords
- seed material
- polymerization
- polymer
- particles
- 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.)
- Expired - Lifetime
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- 239000002245 particle Substances 0.000 title claims abstract description 137
- 229920000642 polymer Polymers 0.000 title claims abstract description 72
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 239000000178 monomer Substances 0.000 claims abstract description 85
- 238000000034 method Methods 0.000 claims abstract description 68
- 239000000463 material Substances 0.000 claims abstract description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 39
- 230000008569 process Effects 0.000 claims abstract description 35
- 238000010557 suspension polymerization reaction Methods 0.000 claims abstract description 30
- 239000003381 stabilizer Substances 0.000 claims abstract description 28
- 239000006185 dispersion Substances 0.000 claims abstract description 18
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 15
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 13
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 238000006116 polymerization reaction Methods 0.000 claims description 54
- 239000003112 inhibitor Substances 0.000 claims description 18
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical group [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 16
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 3
- 239000006260 foam Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 239000004604 Blowing Agent Substances 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 239000013618 particulate matter Substances 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 69
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 9
- 239000011324 bead Substances 0.000 description 35
- 239000000839 emulsion Substances 0.000 description 35
- 239000000047 product Substances 0.000 description 32
- 239000000725 suspension Substances 0.000 description 26
- 238000007792 addition Methods 0.000 description 25
- 239000003999 initiator Substances 0.000 description 23
- 235000019400 benzoyl peroxide Nutrition 0.000 description 20
- 239000004793 Polystyrene Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 19
- 238000004519 manufacturing process Methods 0.000 description 18
- 229920002223 polystyrene Polymers 0.000 description 18
- 238000009826 distribution Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- -1 pentane Chemical class 0.000 description 14
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 13
- 239000004342 Benzoyl peroxide Substances 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 9
- 239000001506 calcium phosphate Substances 0.000 description 8
- 229920003086 cellulose ether Polymers 0.000 description 8
- 238000009331 sowing Methods 0.000 description 8
- 150000003440 styrenes Chemical class 0.000 description 8
- 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 8
- 229940078499 tricalcium phosphate Drugs 0.000 description 7
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 7
- 235000019731 tricalcium phosphate Nutrition 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000004913 activation Effects 0.000 description 6
- 239000007900 aqueous suspension Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 5
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- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- 229920003091 Methocel™ Polymers 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 229920001213 Polysorbate 20 Polymers 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229920006248 expandable polystyrene Polymers 0.000 description 4
- 239000005022 packaging material Substances 0.000 description 4
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 4
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical compound NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 description 3
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-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
- 229920013820 alkyl cellulose Polymers 0.000 description 3
- 238000000137 annealing Methods 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000003380 propellant Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-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
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
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- 238000009792 diffusion process Methods 0.000 description 2
- 238000012674 dispersion polymerization Methods 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- ZBJVLWIYKOAYQH-UHFFFAOYSA-N naphthalen-2-yl 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=C(C=CC=C2)C2=C1 ZBJVLWIYKOAYQH-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
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
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- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
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- 229920000573 polyethylene Polymers 0.000 description 2
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- 239000011347 resin Substances 0.000 description 2
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- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- DEIGXXQKDWULML-UHFFFAOYSA-N 1,2,5,6,9,10-hexabromocyclododecane Chemical compound BrC1CCC(Br)C(Br)CCC(Br)C(Br)CCC1Br DEIGXXQKDWULML-UHFFFAOYSA-N 0.000 description 1
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
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- OQYUFQVPURDFKC-UHFFFAOYSA-N 2-methylbut-1-enylbenzene Chemical compound CCC(C)=CC1=CC=CC=C1 OQYUFQVPURDFKC-UHFFFAOYSA-N 0.000 description 1
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- MUZDXNQOSGWMJJ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(=C)C(O)=O MUZDXNQOSGWMJJ-UHFFFAOYSA-N 0.000 description 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
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- VRKQEIXDEZVPSY-UHFFFAOYSA-N 4-n-phenyl-4-n-propan-2-ylbenzene-1,4-diamine Chemical compound C=1C=C(N)C=CC=1N(C(C)C)C1=CC=CC=C1 VRKQEIXDEZVPSY-UHFFFAOYSA-N 0.000 description 1
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
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- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
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- 239000001273 butane Substances 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 229940042935 dichlorodifluoromethane Drugs 0.000 description 1
- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 1
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 description 1
- XZTWHWHGBBCSMX-UHFFFAOYSA-J dimagnesium;phosphonato phosphate Chemical compound [Mg+2].[Mg+2].[O-]P([O-])(=O)OP([O-])([O-])=O XZTWHWHGBBCSMX-UHFFFAOYSA-J 0.000 description 1
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 description 1
- 229960004419 dimethyl fumarate Drugs 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 241000264288 mixed libraries Species 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229960000502 poloxamer Drugs 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005597 polymer membrane Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012508 resin bead Substances 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
- C08J9/16—Making expandable particles
- C08J9/18—Making expandable particles by impregnating polymer particles with the blowing agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
- C08F257/02—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00 on to polymers of styrene or alkyl-substituted styrenes
-
- 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
- C08J2203/00—Foams characterized by the expanding agent
- C08J2203/12—Organic compounds only containing carbon, hydrogen and oxygen atoms, e.g. ketone or alcohol
-
- 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
- C08J2351/00—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polymerisation Methods In General (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Graft Or Block Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9908164.8A GB9908164D0 (en) | 1999-04-09 | 1999-04-09 | Process |
| GB9908164 | 1999-04-09 | ||
| GB0007006A GB0007006D0 (en) | 1999-04-09 | 2000-03-22 | Preparation of polymer particles |
| GB0007006 | 2000-03-22 | ||
| PCT/GB2000/001335 WO2000061648A1 (en) | 1999-04-09 | 2000-04-10 | Preparation of polymer particles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60025475D1 DE60025475D1 (de) | 2006-04-06 |
| DE60025475T2 true DE60025475T2 (de) | 2006-09-14 |
Family
ID=26243943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60025475T Expired - Lifetime DE60025475T2 (de) | 1999-04-09 | 2000-04-10 | Herstellung von polymerteilchen |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6559217B1 (https=) |
| EP (1) | EP1171494B1 (https=) |
| JP (1) | JP2002542319A (https=) |
| KR (1) | KR100701362B1 (https=) |
| CN (1) | CN1158318C (https=) |
| AT (1) | ATE315595T1 (https=) |
| AU (1) | AU3829700A (https=) |
| CA (1) | CA2364563C (https=) |
| DE (1) | DE60025475T2 (https=) |
| ES (1) | ES2251367T3 (https=) |
| NO (1) | NO328282B1 (https=) |
| PL (1) | PL198386B1 (https=) |
| WO (1) | WO2000061648A1 (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6984702B2 (en) * | 2000-03-22 | 2006-01-10 | Dynal Biotech Asa | Process for the preparation of functionalized polymer particles |
| DE10063299A1 (de) * | 2000-12-19 | 2002-06-20 | Bayer Ag | Iodharze |
| US6896905B2 (en) * | 2001-02-15 | 2005-05-24 | Rohm And Haas Company | Porous particles, their aqueous dispersions, and method of preparation |
| US6632531B2 (en) * | 2001-02-15 | 2003-10-14 | Rohm And Haas Company | Porous particles, their aqueous dispersions, and method of preparation |
| CA2532711C (en) | 2003-07-17 | 2013-07-23 | Dynal Biotech Asa | Coating of porous, surface functionalized, superparamagnetic crystal-containing polymer particles with polyisocyanate/diol and/or epoxide monomers |
| TWI361201B (en) * | 2006-10-26 | 2012-04-01 | Sekisui Plastics | Formable polystyrene resin particles and production process thereof, pre-foamed particles and foam molded product |
| KR100927086B1 (ko) | 2006-11-06 | 2009-11-13 | 주식회사 엘지화학 | 시드 유화 중합에 의한 복합 나노 입자의 제조방법 |
| JP5097506B2 (ja) | 2007-11-05 | 2012-12-12 | 日東電工株式会社 | 水酸基を有する多孔質樹脂粒子の製造方法 |
| GB0907372D0 (en) * | 2009-04-29 | 2009-06-10 | Invitrogen Dynal As | Particles |
| CN102241798A (zh) * | 2010-05-11 | 2011-11-16 | 湖北大学 | 一种由废旧聚苯乙烯泡沫塑料制造合成树脂的方法 |
| EP2581392B1 (en) * | 2010-06-10 | 2018-05-30 | Mitsubishi Chemical Corporation | Process for production of acrylic polymer, acrylic polymer obtained by the process, and plastisol composition using same |
| CN104011086A (zh) | 2011-12-21 | 2014-08-27 | 巴斯夫欧洲公司 | 制备含有颗粒状添加剂的可膨胀苯乙烯聚合物的方法 |
| US20150322182A1 (en) | 2011-12-21 | 2015-11-12 | Patrick Spies | High-temperature peroxide-containing styrene polymer beads for seed polymerization |
| CN102911317A (zh) * | 2012-09-29 | 2013-02-06 | 东莞新长桥塑料有限公司 | 一种超大粒径可发性聚苯乙烯树脂及其制备方法 |
| CN102875734B (zh) * | 2012-09-29 | 2014-08-06 | 东莞新长桥塑料有限公司 | 回收级可发性聚苯乙烯以及利用种子聚合法制备回收级可发性聚苯乙烯的方法 |
| JP5845292B2 (ja) * | 2014-01-14 | 2016-01-20 | 株式会社ジェイエスピー | ポリオレフィン系樹脂粒子、ポリオレフィン系樹脂発泡粒子及びポリオレフィン系樹脂発泡粒子の製造方法 |
| CN104788709A (zh) * | 2015-04-17 | 2015-07-22 | 张家港市山牧新材料技术开发有限公司 | 一种超大粒径复合橡胶改性聚苯乙烯树脂的制备方法 |
| WO2017090792A1 (ko) * | 2015-11-26 | 2017-06-01 | 한국기초과학지원연구원 | 유해 물질의 이온 이동도 측정 장치 및 그의 레퍼런스 데이터 획득방법 |
| JP7338316B2 (ja) | 2018-08-31 | 2023-09-05 | 株式会社リコー | 樹脂粉末、及び立体造形物の製造方法 |
| KR102538844B1 (ko) * | 2018-12-21 | 2023-06-01 | 주식회사 엘지화학 | 방향족 비닐 화합물-비닐시안 화합물 공중합체의 제조방법 및 이를 포함하는 열가소성 수지 조성물의 제조방법 |
| CN117321088A (zh) * | 2021-04-16 | 2023-12-29 | 深圳华大基因科技有限公司 | 用室温引发法制备单分散聚合物珠 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2238718A1 (en) * | 1973-07-27 | 1975-02-21 | Sekisui Chemical Co Ltd | Polystyrene particles of uniform size, esp. for foams - by polymerising in suspension of fine polystyrene particles, contg. catalyst and polymn retarder |
| AU530410B2 (en) * | 1978-02-21 | 1983-07-14 | Sintef | Preparing aqueous emulsions |
| JPS5770111A (en) * | 1980-10-20 | 1982-04-30 | Badische Yuka Co Ltd | Production of styrene polymer particle |
| NO149108C (no) * | 1981-10-21 | 1984-02-15 | Sintef | Fremgangsmaate for fremstilling av vandige dispersjoner av organisk materiale og eventuelt videre omdannelse til en polymerdispersjon naar det organiske materiale er en polymeriserbar monomer |
| US4564644A (en) * | 1982-08-02 | 1986-01-14 | The Dow Chemical Company | Ion exchange resins prepared by sequential monomer addition |
| JPH0674285B2 (ja) * | 1985-01-30 | 1994-09-21 | 日本合成ゴム株式会社 | 重合体粒子の製造方法 |
| JPS61283607A (ja) * | 1985-06-11 | 1986-12-13 | Japan Synthetic Rubber Co Ltd | 液晶装置用スペーサの製造方法 |
| US4652609A (en) * | 1985-11-29 | 1987-03-24 | Atlantic Richfield Company | Modified styrenic polymer beads |
| US4661386A (en) * | 1985-11-29 | 1987-04-28 | Atlantic Richfield Company | High strength foamed articles |
| JPH0264104A (ja) * | 1988-08-31 | 1990-03-05 | Asahi Chem Ind Co Ltd | 重合体粒子の製造方法 |
| BE1007648A3 (fr) * | 1993-10-21 | 1995-09-05 | Solvay | Procede pour la polymerisation radicalaire du chlorure de vinyle a ph acide en dispersion aqueuse. |
| GB9721603D0 (en) * | 1997-10-10 | 1997-12-10 | Dyno Ind Asa | Method |
| TW515816B (en) * | 1997-10-10 | 2003-01-01 | Polymer Systems As | Method of production of particulate polymers |
-
2000
- 2000-04-10 US US09/958,414 patent/US6559217B1/en not_active Expired - Fee Related
- 2000-04-10 DE DE60025475T patent/DE60025475T2/de not_active Expired - Lifetime
- 2000-04-10 KR KR1020017012912A patent/KR100701362B1/ko not_active Expired - Fee Related
- 2000-04-10 ES ES00917205T patent/ES2251367T3/es not_active Expired - Lifetime
- 2000-04-10 AU AU38297/00A patent/AU3829700A/en not_active Abandoned
- 2000-04-10 EP EP00917205A patent/EP1171494B1/en not_active Expired - Lifetime
- 2000-04-10 JP JP2000611585A patent/JP2002542319A/ja active Pending
- 2000-04-10 AT AT00917205T patent/ATE315595T1/de not_active IP Right Cessation
- 2000-04-10 CN CNB008070210A patent/CN1158318C/zh not_active Expired - Fee Related
- 2000-04-10 CA CA2364563A patent/CA2364563C/en not_active Expired - Lifetime
- 2000-04-10 PL PL350621A patent/PL198386B1/pl not_active IP Right Cessation
- 2000-04-10 WO PCT/GB2000/001335 patent/WO2000061648A1/en not_active Ceased
-
2001
- 2001-10-04 NO NO20014836A patent/NO328282B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATE315595T1 (de) | 2006-02-15 |
| NO20014836L (no) | 2001-12-05 |
| CA2364563A1 (en) | 2000-10-19 |
| PL198386B1 (pl) | 2008-06-30 |
| DE60025475D1 (de) | 2006-04-06 |
| EP1171494B1 (en) | 2006-01-11 |
| US6559217B1 (en) | 2003-05-06 |
| AU3829700A (en) | 2000-11-14 |
| PL350621A1 (en) | 2003-01-27 |
| KR100701362B1 (ko) | 2007-03-29 |
| JP2002542319A (ja) | 2002-12-10 |
| NO20014836D0 (no) | 2001-10-04 |
| ES2251367T3 (es) | 2006-05-01 |
| KR20020000556A (ko) | 2002-01-05 |
| EP1171494A1 (en) | 2002-01-16 |
| NO328282B1 (no) | 2010-01-25 |
| CN1158318C (zh) | 2004-07-21 |
| CN1352658A (zh) | 2002-06-05 |
| CA2364563C (en) | 2011-01-04 |
| WO2000061648A1 (en) | 2000-10-19 |
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|---|---|---|---|
| 8364 | No opposition during term of opposition |