DE2757514C2 - - Google Patents
Info
- Publication number
- DE2757514C2 DE2757514C2 DE2757514A DE2757514A DE2757514C2 DE 2757514 C2 DE2757514 C2 DE 2757514C2 DE 2757514 A DE2757514 A DE 2757514A DE 2757514 A DE2757514 A DE 2757514A DE 2757514 C2 DE2757514 C2 DE 2757514C2
- Authority
- DE
- Germany
- Prior art keywords
- tert
- hexyl
- cyclohexene
- acid
- butylperoxycarbonyl
- 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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 65
- 238000006116 polymerization reaction Methods 0.000 claims description 37
- 239000003999 initiator Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 18
- 229920001971 elastomer Polymers 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000000806 elastomer Substances 0.000 claims description 12
- 229920006337 unsaturated polyester resin Polymers 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 11
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 10
- 229920006305 unsaturated polyester Polymers 0.000 claims description 6
- 229920002857 polybutadiene Polymers 0.000 claims description 5
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 3
- 229920000428 triblock copolymer Polymers 0.000 claims description 3
- 239000005062 Polybutadiene Substances 0.000 claims description 2
- 125000005725 cyclohexenylene group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 70
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- -1 alkyl radicals Chemical class 0.000 description 45
- 239000004793 Polystyrene Substances 0.000 description 34
- 229920002223 polystyrene Polymers 0.000 description 34
- 239000000243 solution Substances 0.000 description 34
- 239000002253 acid Substances 0.000 description 30
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 24
- 229920000642 polymer Polymers 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 19
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 14
- 150000007513 acids Chemical class 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 11
- 238000009826 distribution Methods 0.000 description 11
- 150000002978 peroxides Chemical class 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 229920005669 high impact polystyrene Polymers 0.000 description 8
- 239000004797 high-impact polystyrene Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 235000011118 potassium hydroxide Nutrition 0.000 description 8
- 150000001805 chlorine compounds Chemical class 0.000 description 7
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 7
- 238000000465 moulding Methods 0.000 description 7
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 235000020778 linoleic acid Nutrition 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 6
- 239000004926 polymethyl methacrylate Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- MKQBLYMEKNJFOX-UHFFFAOYSA-N 3-(8-chloro-8-oxooctyl)-6-hexylcyclohex-4-ene-1,2-dicarbonyl chloride Chemical compound CCCCCCC1C=CC(CCCCCCCC(Cl)=O)C(C(Cl)=O)C1C(Cl)=O MKQBLYMEKNJFOX-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 238000005698 Diels-Alder reaction Methods 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000002274 desiccant Substances 0.000 description 4
- 239000012933 diacyl peroxide Substances 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- 239000012263 liquid product Substances 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 229920001225 polyester resin Polymers 0.000 description 4
- 239000004645 polyester resin Substances 0.000 description 4
- 238000003825 pressing Methods 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- YKTNISGZEGZHIS-UHFFFAOYSA-N 2-$l^{1}-oxidanyloxy-2-methylpropane Chemical group CC(C)(C)O[O] YKTNISGZEGZHIS-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- XRXANEMIFVRKLN-UHFFFAOYSA-N 2-hydroperoxy-2-methylbutane Chemical compound CCC(C)(C)OO XRXANEMIFVRKLN-UHFFFAOYSA-N 0.000 description 3
- KBDBSDQDTRPGOC-UHFFFAOYSA-N 5-(8-chloro-8-oxooctyl)-2-hexylcyclohex-3-ene-1-carbonyl chloride Chemical compound CCCCCCC1C=CC(CCCCCCCC(Cl)=O)CC1C(Cl)=O KBDBSDQDTRPGOC-UHFFFAOYSA-N 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- 239000004604 Blowing Agent Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229920000180 alkyd Polymers 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000002976 peresters Chemical class 0.000 description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000005297 pyrex Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- 229920001897 terpolymer Polymers 0.000 description 3
- 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 description 3
- LAXMMAYMKLLBQC-UHFFFAOYSA-N tert-butyl 2-(9-tert-butylperoxy-9-oxononyl)-5-pentylcyclohexane-1-carboperoxoate Chemical compound CCCCCC1CCC(CCCCCCCCC(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)C1 LAXMMAYMKLLBQC-UHFFFAOYSA-N 0.000 description 3
- GKJZMAHZJGSBKD-UHFFFAOYSA-N (10E,12E)-Octadeca-9,11-dienoic acid Natural products CCCCCC=CC=CCCCCCCCCC(O)=O GKJZMAHZJGSBKD-UHFFFAOYSA-N 0.000 description 2
- GKJZMAHZJGSBKD-BLHCBFLLSA-N (10e,12e)-octadeca-10,12-dienoic acid Chemical compound CCCCC\C=C\C=C\CCCCCCCCC(O)=O GKJZMAHZJGSBKD-BLHCBFLLSA-N 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 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- GKJZMAHZJGSBKD-ANYPYVPJSA-N 10-trans-12-cis-linoleic acid Natural products CCCCCC=C\C=C\CCCCCCCCC(O)=O GKJZMAHZJGSBKD-ANYPYVPJSA-N 0.000 description 2
- BGPBFIBJAZKFJR-UHFFFAOYSA-N 2,2-dimethylbutanedioyl dichloride Chemical compound ClC(=O)C(C)(C)CC(Cl)=O BGPBFIBJAZKFJR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JMUKALCRCFJQTI-UHFFFAOYSA-N 2-(7-carboxyheptyl)-5-hexylcyclohex-3-ene-1-carboxylic acid Chemical compound CCCCCCC1CC(C(O)=O)C(CCCCCCCC(O)=O)C=C1 JMUKALCRCFJQTI-UHFFFAOYSA-N 0.000 description 2
- AEHPCEISAZSQHX-UHFFFAOYSA-N 2-(8-carboxyoctyl)-5-pentylcyclohex-3-ene-1-carboxylic acid Chemical compound CCCCCC1CC(C(O)=O)C(CCCCCCCCC(O)=O)C=C1 AEHPCEISAZSQHX-UHFFFAOYSA-N 0.000 description 2
- RMHNLLYQAWIDQE-UHFFFAOYSA-N 2-(8-chloro-8-oxooctyl)-5-hexylcyclohex-3-ene-1-carbonyl chloride Chemical compound CCCCCCC1CC(C(Cl)=O)C(CCCCCCCC(Cl)=O)C=C1 RMHNLLYQAWIDQE-UHFFFAOYSA-N 0.000 description 2
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 2
- WPAJONGYCAHYII-UHFFFAOYSA-N 2-octylbutanedioyl dichloride Chemical compound CCCCCCCCC(C(Cl)=O)CC(Cl)=O WPAJONGYCAHYII-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- RYKIXDBAIYMFDV-UHFFFAOYSA-N 5-(7-carboxyheptyl)-2-hexylcyclohex-3-ene-1-carboxylic acid Chemical compound CCCCCCC1C=CC(CCCCCCCC(O)=O)CC1C(O)=O RYKIXDBAIYMFDV-UHFFFAOYSA-N 0.000 description 2
- MVNKYWIYFHYPRE-UHFFFAOYSA-N 5-(8-chloro-8-oxooctyl)-2-hexylcyclohexane-1-carbonyl chloride Chemical compound CCCCCCC1CCC(CCCCCCCC(Cl)=O)CC1C(Cl)=O MVNKYWIYFHYPRE-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-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
- 239000004641 Diallyl-phthalate Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 229920002633 Kraton (polymer) Polymers 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- DIGVLYGOCZUOMK-UHFFFAOYSA-N acetyl 2-(8-acetylperoxy-8-oxooctyl)-5-hexylcyclohex-3-ene-1-carboperoxoate Chemical compound CCCCCCC1CC(C(=O)OOC(C)=O)C(CCCCCCCC(=O)OOC(C)=O)C=C1 DIGVLYGOCZUOMK-UHFFFAOYSA-N 0.000 description 2
- NTOFFYXWSUKHMJ-UHFFFAOYSA-N acetyl 2-(9-acetylperoxy-9-oxononyl)-5-pentylcyclohex-3-ene-1-carboperoxoate Chemical compound CCCCCC1CC(C(=O)OOC(C)=O)C(CCCCCCCCC(=O)OOC(C)=O)C=C1 NTOFFYXWSUKHMJ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 230000002902 bimodal effect Effects 0.000 description 2
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
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- DLDJFQGPPSQZKI-UHFFFAOYSA-N but-2-yne-1,4-diol Chemical compound OCC#CCO DLDJFQGPPSQZKI-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical group CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019241 carbon black Nutrition 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- DJKGDNKYTKCJKD-UHFFFAOYSA-N chlorendic acid Chemical compound ClC1=C(Cl)C2(Cl)C(C(=O)O)C(C(O)=O)C1(Cl)C2(Cl)Cl DJKGDNKYTKCJKD-UHFFFAOYSA-N 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- 150000001935 cyclohexenes Chemical class 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- VEOMCUUTIYXSLV-UHFFFAOYSA-N ditert-butyl 2-methylbutanediperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)CC(=O)OOC(C)(C)C VEOMCUUTIYXSLV-UHFFFAOYSA-N 0.000 description 1
- YUSUEMQQBKFEKP-UHFFFAOYSA-N ditert-butyl 3-(8-tert-butylperoxy-8-oxooctyl)-6-hexylcyclohexane-1,2-dicarboperoxoate Chemical compound CCCCCCC1CCC(CCCCCCCC(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)C1C(=O)OOC(C)(C)C YUSUEMQQBKFEKP-UHFFFAOYSA-N 0.000 description 1
- DRJRXYGVRCGCCV-UHFFFAOYSA-N ditert-butyl 3-(9-tert-butylperoxy-9-oxononyl)-6-pentylcyclohex-4-ene-1,2-dicarboperoxoate Chemical compound CCCCCC1C=CC(CCCCCCCCC(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)C1C(=O)OOC(C)(C)C DRJRXYGVRCGCCV-UHFFFAOYSA-N 0.000 description 1
- FLMIYNBKUUWQLE-UHFFFAOYSA-N ditert-butyl 3-(9-tert-butylperoxy-9-oxononyl)-6-pentylcyclohexane-1,2-dicarboperoxoate Chemical compound CCCCCC1CCC(CCCCCCCCC(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)C1C(=O)OOC(C)(C)C FLMIYNBKUUWQLE-UHFFFAOYSA-N 0.000 description 1
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- UZAYBTVEHRBXQL-UHFFFAOYSA-N dodecanoyl 5-(8-acetylperoxy-8-oxooctyl)-2-hexylcyclohex-3-ene-1-carboperoxoate Chemical compound CCCCCCCCCCCC(=O)OOC(=O)C1CC(CCCCCCCC(=O)OOC(C)=O)C=CC1CCCCCC UZAYBTVEHRBXQL-UHFFFAOYSA-N 0.000 description 1
- LPOMTYCMNVIYGL-UHFFFAOYSA-N dodecanoyl 5-(8-dodecanoylperoxy-8-oxooctyl)-2-hexylcyclohex-3-ene-1-carboperoxoate Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCC1CC(C(=O)OOC(=O)CCCCCCCCCCC)C(CCCCCC)C=C1 LPOMTYCMNVIYGL-UHFFFAOYSA-N 0.000 description 1
- NCZIZDOSDOAVDJ-UHFFFAOYSA-N dodecanoyl 5-(8-dodecanoylperoxy-8-oxooctyl)-2-hexylcyclohexane-1-carboperoxoate Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCC1CCC(CCCCCC)C(C(=O)OOC(=O)CCCCCCCCCCC)C1 NCZIZDOSDOAVDJ-UHFFFAOYSA-N 0.000 description 1
- HGQVWMYCNURFBP-UHFFFAOYSA-N dodecanoyl 5-(9-dodecanoylperoxy-9-oxononyl)-2-pentylcyclohex-3-ene-1-carboperoxoate Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCC1CC(C(=O)OOC(=O)CCCCCCCCCCC)C(CCCCC)C=C1 HGQVWMYCNURFBP-UHFFFAOYSA-N 0.000 description 1
- LHNAKKDFNGVGJR-UHFFFAOYSA-N dodecanoyl 5-(9-dodecanoylperoxy-9-oxononyl)-2-pentylcyclohexane-1-carboperoxoate Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCC1CCC(CCCCC)C(C(=O)OOC(=O)CCCCCCCCCCC)C1 LHNAKKDFNGVGJR-UHFFFAOYSA-N 0.000 description 1
- 238000010556 emulsion polymerization method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- BGSFCOHRQUBESL-UHFFFAOYSA-N ethyl prop-2-enyl carbonate Chemical compound CCOC(=O)OCC=C BGSFCOHRQUBESL-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
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- 239000007789 gas Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- NQUPKCJGWCPODR-UHFFFAOYSA-N hexaneperoxoic acid Chemical compound CCCCCC(=O)OO NQUPKCJGWCPODR-UHFFFAOYSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052914 metal silicate Inorganic materials 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- ZFACJPAPCXRZMQ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O.OC(=O)C1=CC=CC=C1C(O)=O ZFACJPAPCXRZMQ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000002990 reinforced plastic Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- RPAVVGWQTDWFLW-UHFFFAOYSA-N tert-butyl 2-(8-tert-butylperoxy-8-oxooctyl)-5-hexyl-1-methylcyclohex-3-ene-1-carboperoxoate Chemical compound CCCCCCC1CC(C)(C(=O)OOC(C)(C)C)C(CCCCCCCC(=O)OOC(C)(C)C)C=C1 RPAVVGWQTDWFLW-UHFFFAOYSA-N 0.000 description 1
- CENFGFRVEHLMRC-UHFFFAOYSA-N tert-butyl 2-(8-tert-butylperoxy-8-oxooctyl)-5-hexyl-1-methylcyclohexane-1-carboperoxoate Chemical compound CCCCCCC1CCC(CCCCCCCC(=O)OOC(C)(C)C)C(C)(C(=O)OOC(C)(C)C)C1 CENFGFRVEHLMRC-UHFFFAOYSA-N 0.000 description 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 description 1
- DOLRJIABTVKKGE-UHFFFAOYSA-N tert-butyl 2-(8-tert-butylperoxy-8-oxooctyl)-5-hexylcyclohexane-1-carboperoxoate Chemical compound CCCCCCC1CCC(CCCCCCCC(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)C1 DOLRJIABTVKKGE-UHFFFAOYSA-N 0.000 description 1
- JONDLWAXOJNANP-UHFFFAOYSA-N tert-butyl 2-(9-tert-butylperoxy-9-oxononyl)-1-methyl-5-pentylcyclohex-3-ene-1-carboperoxoate Chemical compound CCCCCC1CC(C)(C(=O)OOC(C)(C)C)C(CCCCCCCCC(=O)OOC(C)(C)C)C=C1 JONDLWAXOJNANP-UHFFFAOYSA-N 0.000 description 1
- SJUPTGQYWYBLMO-UHFFFAOYSA-N tert-butyl 2-(9-tert-butylperoxy-9-oxononyl)-1-methyl-5-pentylcyclohexane-1-carboperoxoate Chemical compound CCCCCC1CCC(CCCCCCCCC(=O)OOC(C)(C)C)C(C)(C(=O)OOC(C)(C)C)C1 SJUPTGQYWYBLMO-UHFFFAOYSA-N 0.000 description 1
- OLOYYTHNHGATJO-UHFFFAOYSA-N tert-butyl 5-(11-tert-butylperoxy-11-oxoundecyl)-2-propylcyclohexane-1-carboperoxoate Chemical compound CCCC1CCC(CCCCCCCCCCC(=O)OOC(C)(C)C)CC1C(=O)OOC(C)(C)C OLOYYTHNHGATJO-UHFFFAOYSA-N 0.000 description 1
- NCEBXZGMLFKRCQ-UHFFFAOYSA-N tert-butyl 5-(12-tert-butylperoxy-12-oxododecyl)-2-ethylcyclohexane-1-carboperoxoate Chemical compound CCC1CCC(CCCCCCCCCCCC(=O)OOC(C)(C)C)CC1C(=O)OOC(C)(C)C NCEBXZGMLFKRCQ-UHFFFAOYSA-N 0.000 description 1
- AGOZQJZNBYPZIC-UHFFFAOYSA-N tert-butyl 5-(8-tert-butylperoxy-8-oxooctyl)-2-hexyl-1-methylcyclohex-3-ene-1-carboperoxoate Chemical compound CCCCCCC1C=CC(CCCCCCCC(=O)OOC(C)(C)C)CC1(C)C(=O)OOC(C)(C)C AGOZQJZNBYPZIC-UHFFFAOYSA-N 0.000 description 1
- NSWRODQWQOTICC-UHFFFAOYSA-N tert-butyl 5-(9-tert-butylperoxy-9-oxononyl)-1-methyl-2-pentylcyclohex-3-ene-1-carboperoxoate Chemical compound CCCCCC1C=CC(CCCCCCCCC(=O)OOC(C)(C)C)CC1(C)C(=O)OOC(C)(C)C NSWRODQWQOTICC-UHFFFAOYSA-N 0.000 description 1
- OTPQWFGAGJXDPG-UHFFFAOYSA-N tert-butyl 5-(9-tert-butylperoxy-9-oxononyl)-1-methyl-2-pentylcyclohexane-1-carboperoxoate Chemical compound CCCCCC1CCC(CCCCCCCCC(=O)OOC(C)(C)C)CC1(C)C(=O)OOC(C)(C)C OTPQWFGAGJXDPG-UHFFFAOYSA-N 0.000 description 1
- DRRPGCLOKQERML-UHFFFAOYSA-N tert-butyl 5-(9-tert-butylperoxy-9-oxononyl)-2-pentylcyclohexane-1-carboperoxoate Chemical compound CCCCCC1CCC(CCCCCCCCC(=O)OOC(C)(C)C)CC1C(=O)OOC(C)(C)C DRRPGCLOKQERML-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/38—Peroxy compounds the —O—O— group being bound between a >C=O group and a carbon atom, not further substituted by oxygen atoms, i.e. esters of peroxy acids
-
- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/04—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters
- C08F299/0442—Catalysts
- C08F299/045—Peroxy-compounds
-
- 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
- C08F4/36—Per-compounds with more than one peroxy radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerization Catalysts (AREA)
- Polyesters Or Polycarbonates (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/757,185 US4079074A (en) | 1977-01-06 | 1977-01-06 | Unsymmetrical diperoxides and processes of use in polymerizing unsaturated monomers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2757514A1 DE2757514A1 (de) | 1978-07-13 |
| DE2757514C2 true DE2757514C2 (en, 2012) | 1988-02-25 |
Family
ID=25046752
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772757514 Granted DE2757514A1 (de) | 1977-01-06 | 1977-12-22 | Unsymmetrische diperoxide |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4079074A (en, 2012) |
| JP (1) | JPS5387338A (en, 2012) |
| AU (1) | AU509887B2 (en, 2012) |
| CA (1) | CA1085416A (en, 2012) |
| DE (1) | DE2757514A1 (en, 2012) |
| FR (1) | FR2376843A1 (en, 2012) |
| GB (1) | GB1580820A (en, 2012) |
| IT (1) | IT1091786B (en, 2012) |
| NL (1) | NL7800023A (en, 2012) |
| SE (1) | SE436567B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4219676A (en) * | 1978-01-16 | 1980-08-26 | Pennwalt Corporation | Unsymmetrical diperoxides and processes of use in polymerizing unsaturated monomers |
| US4634753A (en) * | 1983-05-20 | 1987-01-06 | Pennwalt Corporation | Hydroxy-t-alkyl peroxyester |
| US4705888A (en) * | 1985-09-30 | 1987-11-10 | Akzo Nv | t-Alkenyl peroxy esters |
| 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 |
| CA2019626C (en) * | 1989-06-30 | 1994-11-22 | Yuichi Arito | Styrene type resin and production method thereof |
| AU666094B2 (en) * | 1992-06-10 | 1996-01-25 | Dow Chemical Company, The | Oligomers of styrene as flegmatizers for organic peroxides |
| US6703460B1 (en) * | 2003-03-04 | 2004-03-09 | Fina Technology, Inc. | Use of sequential polyperoxides to produce polystyrene with high grafting |
| JP5707948B2 (ja) | 2011-01-12 | 2015-04-30 | 株式会社豊田自動織機 | エアコンプレッサ |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2813885A (en) * | 1954-09-02 | 1957-11-19 | Swern Daniel | Process for making fatty peracids |
| US3770770A (en) * | 1966-08-01 | 1973-11-06 | Pennwalt Corp | Certain peroxyesters having a defined substituent positioned on a carbon atom at least beta to a peroxy carbon atom |
| US3494898A (en) * | 1969-04-10 | 1970-02-10 | Heinz W Meyer | Polymerization of olefinic compounds and polymerization catalyst |
| DE2125160C3 (de) * | 1971-05-21 | 1980-05-22 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Verfahren zur Herstellung von aliphatischen Percarbonsäuren mit 2 bis 5 Kohlenstoffatomen |
| NL7209462A (en, 2012) * | 1972-07-07 | 1974-01-09 | ||
| NL7311783A (nl) * | 1973-08-28 | 1975-03-04 | Akzo Nv | Werkwijze voor het bereiden van voor het initieren van radicaalreacties geschikte nieuwe peresters. |
-
1977
- 1977-01-06 US US05/757,185 patent/US4079074A/en not_active Expired - Lifetime
- 1977-10-19 CA CA289,031A patent/CA1085416A/en not_active Expired
- 1977-11-03 SE SE7712454A patent/SE436567B/xx not_active IP Right Cessation
- 1977-11-15 IT IT51820/77A patent/IT1091786B/it active
- 1977-11-24 AU AU30918/77A patent/AU509887B2/en not_active Expired
- 1977-11-24 GB GB49008/77A patent/GB1580820A/en not_active Expired
- 1977-12-16 FR FR7738072A patent/FR2376843A1/fr active Granted
- 1977-12-22 DE DE19772757514 patent/DE2757514A1/de active Granted
-
1978
- 1978-01-02 NL NL7800023A patent/NL7800023A/xx not_active Application Discontinuation
- 1978-01-05 JP JP5078A patent/JPS5387338A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4079074A (en) | 1978-03-14 |
| SE7712454L (sv) | 1978-07-07 |
| AU3091877A (en) | 1979-05-31 |
| JPS5387338A (en) | 1978-08-01 |
| DE2757514A1 (de) | 1978-07-13 |
| JPS642587B2 (en, 2012) | 1989-01-18 |
| CA1085416A (en) | 1980-09-09 |
| IT1091786B (it) | 1985-07-06 |
| FR2376843B1 (en, 2012) | 1981-10-16 |
| AU509887B2 (en) | 1980-05-29 |
| GB1580820A (en) | 1980-12-03 |
| NL7800023A (nl) | 1978-07-10 |
| SE436567B (sv) | 1985-01-07 |
| FR2376843A1 (fr) | 1978-08-04 |
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