DE2757427C2 - - Google Patents
Info
- Publication number
- DE2757427C2 DE2757427C2 DE2757427A DE2757427A DE2757427C2 DE 2757427 C2 DE2757427 C2 DE 2757427C2 DE 2757427 A DE2757427 A DE 2757427A DE 2757427 A DE2757427 A DE 2757427A DE 2757427 C2 DE2757427 C2 DE 2757427C2
- Authority
- DE
- Germany
- Prior art keywords
- polymerization
- initiator
- temperature
- phm
- molecular weight
- 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
Links
- 239000003999 initiator Substances 0.000 claims description 146
- 238000006116 polymerization reaction Methods 0.000 claims description 94
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 44
- 239000000178 monomer Substances 0.000 claims description 30
- 230000008569 process Effects 0.000 claims description 20
- 150000003254 radicals Chemical class 0.000 claims description 16
- 229920002554 vinyl polymer Polymers 0.000 claims description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- -1 azo peroxide Chemical class 0.000 claims description 8
- 150000002978 peroxides Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
- 238000010526 radical polymerization reaction Methods 0.000 claims description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 239000007870 radical polymerization initiator Substances 0.000 claims 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- WVNZGKREVGWRMP-UHFFFAOYSA-N tert-butyl 2-(8-tert-butylperoxy-8-oxooctyl)-5-hexylcyclohex-3-ene-1-carboperoxoate Chemical compound CCCCCCC1CC(C(=O)OOC(C)(C)C)C(CCCCCCCC(=O)OOC(C)(C)C)C=C1 WVNZGKREVGWRMP-UHFFFAOYSA-N 0.000 claims 1
- FQIAVTKBJAWIQS-UHFFFAOYSA-N tert-butyl 2-(9-tert-butylperoxy-9-oxononyl)-5-pentylcyclohex-3-ene-1-carboperoxoate Chemical compound CCCCCC1CC(C(=O)OOC(C)(C)C)C(CCCCCCCCC(=O)OOC(C)(C)C)C=C1 FQIAVTKBJAWIQS-UHFFFAOYSA-N 0.000 claims 1
- DQOJSNMSECZJJM-UHFFFAOYSA-N tert-butyl 4-[(5-tert-butylperoxy-2-cyano-5-oxopentan-2-yl)diazenyl]-4-cyanopentaneperoxoate Chemical compound CC(C)(C)OOC(=O)CCC(C)(C#N)N=NC(C)(C#N)CCC(=O)OOC(C)(C)C DQOJSNMSECZJJM-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 51
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 239000004793 Polystyrene Substances 0.000 description 24
- 230000000737 periodic effect Effects 0.000 description 20
- 238000009826 distribution Methods 0.000 description 18
- 239000004342 Benzoyl peroxide Substances 0.000 description 17
- 235000019400 benzoyl peroxide Nutrition 0.000 description 17
- 238000012662 bulk polymerization Methods 0.000 description 16
- 229920002223 polystyrene Polymers 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 229920001971 elastomer Polymers 0.000 description 10
- 239000000806 elastomer Substances 0.000 description 10
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 9
- CWPKTBMRVATCBL-UHFFFAOYSA-N 3-[1-[1-[(2-methylphenyl)methyl]piperidin-4-yl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound CC1=CC=CC=C1CN1CCC(N2CCC(CC2)N2C(NC3=CC=CC=C32)=O)CC1 CWPKTBMRVATCBL-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NZGSNQJCTOMELT-UHFFFAOYSA-N 3,5-dimethylorsellinic acid Chemical compound CC1=C(C)C(C(O)=O)=C(O)C(C)=C1O NZGSNQJCTOMELT-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 125000002081 peroxide group Chemical group 0.000 description 5
- 239000000375 suspending agent Substances 0.000 description 5
- 238000010557 suspension polymerization reaction Methods 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- CIKJANOSDPPCAU-UHFFFAOYSA-N ditert-butyl cyclohexane-1,4-dicarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1CCC(C(=O)OOC(C)(C)C)CC1 CIKJANOSDPPCAU-UHFFFAOYSA-N 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 230000014509 gene expression Effects 0.000 description 4
- 238000004904 shortening Methods 0.000 description 4
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 3
- 230000002902 bimodal effect Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002976 peresters Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 3
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-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
- 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
- QRTGKIRHWUPEBT-UHFFFAOYSA-N 2-o-tert-butyl 1-o-(2-tert-butylperoxycarbonylbenzoyl) benzene-1,2-dicarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1C(=O)OOC(C)(C)C QRTGKIRHWUPEBT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 239000006172 buffering agent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 2
- 229920006248 expandable polystyrene Polymers 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 238000013519 translation Methods 0.000 description 2
- HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 1
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
- 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
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- QKNQPCLQRXMWJO-UHFFFAOYSA-N 1-(tert-butyldiazenyl)cyclohexane-1-carbonitrile Chemical compound CC(C)(C)N=NC1(C#N)CCCCC1 QKNQPCLQRXMWJO-UHFFFAOYSA-N 0.000 description 1
- NMHMROMMTKMZLD-UHFFFAOYSA-N 2,2-ditert-butyl-3-octylbutanediperoxoic acid Chemical compound CCCCCCCCC(C(=O)OO)C(C(=O)OO)(C(C)(C)C)C(C)(C)C NMHMROMMTKMZLD-UHFFFAOYSA-N 0.000 description 1
- ODKBBGGUUMCXFY-UHFFFAOYSA-N 2-(2-cyanopentan-2-yldiazenyl)-2-methylpentanenitrile Chemical compound CCCC(C)(C#N)N=NC(C)(C#N)CCC ODKBBGGUUMCXFY-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PYKCEDJHRUUDRK-UHFFFAOYSA-N 2-(tert-butyldiazenyl)-2-methylpropanenitrile Chemical compound CC(C)(C)N=NC(C)(C)C#N PYKCEDJHRUUDRK-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- NNWNNQTUZYVQRK-UHFFFAOYSA-N 5-bromo-1h-pyrrolo[2,3-c]pyridine-2-carboxylic acid Chemical compound BrC1=NC=C2NC(C(=O)O)=CC2=C1 NNWNNQTUZYVQRK-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- GYSSVYMXJCUUTF-UHFFFAOYSA-N CC(C)(C)C(C)(C(C)(C(C)(C)C)C(OO)=O)C(OO)=O Chemical compound CC(C)(C)C(C)(C(C)(C(C)(C)C)C(OO)=O)C(OO)=O GYSSVYMXJCUUTF-UHFFFAOYSA-N 0.000 description 1
- 229920002574 CR-39 Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920002633 Kraton (polymer) Polymers 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 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 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- BMFRMJJTMMZETR-UHFFFAOYSA-N dibutyl cyclohexane-1,4-dicarboperoxoate Chemical compound CCCCOOC(=O)C1CCC(CC1)C(=O)OOCCCC BMFRMJJTMMZETR-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- YCWQBZCTYWZZAX-UHFFFAOYSA-N ditert-butyl 7,8-dioxabicyclo[4.2.0]octane-3,6-dicarboxylate Chemical compound C1C(C(=O)OC(C)(C)C)CCC2(C(=O)OC(C)(C)C)OOC21 YCWQBZCTYWZZAX-UHFFFAOYSA-N 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000007425 progressive decline Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical class C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
Classifications
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/28—Oxygen or compounds releasing free oxygen
- C08F4/32—Organic compounds
- C08F4/38—Mixtures of peroxy-compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/757,187 US4125695A (en) | 1977-01-06 | 1977-01-06 | Polymerization process with reduced cycle time employing polyfunctional free radical initiators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2757427A1 DE2757427A1 (de) | 1978-07-20 |
| DE2757427C2 true DE2757427C2 (en, 2012) | 1988-05-19 |
Family
ID=25046764
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772757427 Granted DE2757427A1 (de) | 1977-01-06 | 1977-12-22 | Polymerisationsverfahren mit verkuerzter umlaufzeit |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4125695A (en, 2012) |
| JP (1) | JPS5385881A (en, 2012) |
| CA (1) | CA1092288A (en, 2012) |
| DE (1) | DE2757427A1 (en, 2012) |
| FR (1) | FR2376870A1 (en, 2012) |
| GB (1) | GB1588879A (en, 2012) |
| NL (1) | NL184621B (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54150493A (en) * | 1978-05-18 | 1979-11-26 | Nippon Oil & Fats Co Ltd | Production of styrene polymer or copolymer |
| US4217433A (en) * | 1979-08-03 | 1980-08-12 | Pennwalt Corporation | Diethylene glycol bis(allyl carbonate) compositions containing crosslinkable copolymers |
| US4588798A (en) * | 1985-02-01 | 1986-05-13 | E. I. Du Pont De Nemours And Company | Process for preparing acrylic polymer sheets using a dual peroxide initiator system |
| US4605717A (en) * | 1985-06-21 | 1986-08-12 | E. I. Du Pont De Nemours And Company | Preparation of acrylic polymer sheets using a ternary peroxide initiator system |
| JPH0699529B2 (ja) * | 1985-06-28 | 1994-12-07 | モンサント化成株式会社 | シアン化ビニル化合物／芳香族ビニル化合物共重合樹脂の製造方法 |
| HU201101B (en) * | 1986-11-14 | 1990-09-28 | Mta Koezponti Kemiai Kutato In | Process for producing by radical polymerization of polymers of polydispersity of 1,50 to 2,00, having functional groups in alpha, omega positions |
| US5660776A (en) * | 1995-11-20 | 1997-08-26 | Novacor Chemicals (International) S.A. | Process of making styrenic polymer pellets |
| DE19749570A1 (de) * | 1997-11-10 | 1999-05-12 | Basf Ag | Verfahren zur Herstellung von expandierbaren Styrolpolymerisaten |
| UA77245C2 (uk) * | 2001-12-21 | 2006-11-15 | Акцо Нобель Н.В. | Спосіб полімеризації суміші, яка містить вінілхлоридний мономер |
| US8093332B2 (en) * | 2003-09-29 | 2012-01-10 | Fina Technology, Inc. | High impact polystyrene and process for preparing same |
| US9193839B2 (en) | 2014-03-14 | 2015-11-24 | Fina Technology, Inc. | Crosslinking control in high impact polystyrene manufacturing process |
| CN112390903B (zh) * | 2020-12-03 | 2022-05-13 | 上海科技大学 | 一种以惰性双烯内酯为引发剂制备pmma的方法 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA892672A (en) * | 1972-02-08 | J. Gammon Geoffrey | Polymerisation process | |
| DE668325C (de) * | 1932-05-24 | 1938-11-30 | L Orange Motorzubehoer Geb | Brennstoffkolbenpumpe fuer rasch laufende Einspritzbrennkraftmaschinen |
| US2656334A (en) * | 1948-09-28 | 1953-10-20 | Koppers Co Inc | Catalytic polymerization process |
| BE509277A (en, 2012) * | 1950-12-06 | |||
| US2698863A (en) * | 1952-01-18 | 1955-01-04 | Shell Dev | Peresters of oxo-substitiuted polyperoxycarboxylic acids |
| BE575339A (en, 2012) * | 1958-02-03 | |||
| NL137858C (en, 2012) * | 1962-05-17 | |||
| US3293233A (en) * | 1963-04-09 | 1966-12-20 | Rexall Drug Chemical | Process for polymerizing ethylene at high pressures in the presence of a mixture of peroxides having different half lives |
| NL149816B (nl) * | 1967-08-29 | 1976-06-15 | Noury & Van Der Lande | Werkwijze voor de peroxydische homo- of copolymerisatie van vinylmonomeren. |
| GB1243197A (en) * | 1968-01-18 | 1971-08-18 | British Petroleum Co | Polymerisation process |
| US3817965A (en) * | 1968-02-27 | 1974-06-18 | Aquitaine Petrole | Polymerization of vinyl compounds in suspension |
| GB1243057A (en) * | 1968-02-27 | 1971-08-18 | British Petroleum Co | Styrene polymerisation process |
| GB1252153A (en, 2012) * | 1968-04-30 | 1971-11-03 | ||
| US3965145A (en) * | 1968-06-17 | 1976-06-22 | Pennwalt Corporation | Coupled peroxides |
| US3763129A (en) * | 1968-08-15 | 1973-10-02 | Pennwalt Corp | Polyazo sequential free radical initiators |
| US3649614A (en) * | 1968-08-15 | 1972-03-14 | Pennwalt Corp | Polyazo sequential free radical initiators |
| BE789896A (nl) * | 1971-11-01 | 1973-02-01 | Akzo Nv | Werkwijze voor het uitvoeren van door organische peroxyden geinitieerdechemische reacties |
| GB1391703A (en) * | 1972-04-14 | 1975-04-23 | Denco Miller Ltd | Self contained air cooling and heating unit |
| JPS5347346B2 (en, 2012) * | 1972-06-06 | 1978-12-20 | ||
| JPS4920076A (en, 2012) * | 1972-06-15 | 1974-02-22 | ||
| JPS5033917B2 (en, 2012) * | 1972-10-31 | 1975-11-04 | ||
| JPS581125B2 (ja) * | 1975-04-14 | 1983-01-10 | 住友化学工業株式会社 | タイシヨウゲキセイジユシノセイゾウホウ |
| JPS51119789A (en) * | 1975-04-14 | 1976-10-20 | Sumitomo Chem Co Ltd | Preparation of thermoplastic resins |
-
1977
- 1977-01-06 US US05/757,187 patent/US4125695A/en not_active Expired - Lifetime
- 1977-09-15 CA CA286,839A patent/CA1092288A/en not_active Expired
- 1977-09-19 NL NLAANVRAGE7710246,A patent/NL184621B/xx not_active Application Discontinuation
- 1977-11-16 FR FR7734495A patent/FR2376870A1/fr active Granted
- 1977-11-24 GB GB49006/77A patent/GB1588879A/en not_active Expired
- 1977-12-22 DE DE19772757427 patent/DE2757427A1/de active Granted
-
1978
- 1978-01-05 JP JP5278A patent/JPS5385881A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE2757427A1 (de) | 1978-07-20 |
| NL184621B (nl) | 1989-04-17 |
| FR2376870B1 (en, 2012) | 1984-01-27 |
| JPS5385881A (en) | 1978-07-28 |
| NL7710246A (nl) | 1978-07-10 |
| CA1092288A (en) | 1980-12-23 |
| GB1588879A (en) | 1981-04-29 |
| US4125695A (en) | 1978-11-14 |
| FR2376870A1 (fr) | 1978-08-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8363 | Opposition against the patent | ||
| 8330 | Complete renunciation |