JPS5946273B2 - 安定化ニトリル重合体 - Google Patents
安定化ニトリル重合体Info
- Publication number
- JPS5946273B2 JPS5946273B2 JP51001100A JP110076A JPS5946273B2 JP S5946273 B2 JPS5946273 B2 JP S5946273B2 JP 51001100 A JP51001100 A JP 51001100A JP 110076 A JP110076 A JP 110076A JP S5946273 B2 JPS5946273 B2 JP S5946273B2
- Authority
- JP
- Japan
- Prior art keywords
- weight
- parts
- group
- polymer composition
- structural formula
- 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
- 229920000642 polymer Polymers 0.000 title claims description 30
- 150000002825 nitriles Chemical class 0.000 title claims description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 26
- 239000000178 monomer Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 24
- 239000003381 stabilizer Substances 0.000 claims description 21
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 18
- 229920001971 elastomer Polymers 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 claims description 8
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 6
- 150000001993 dienes Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical class CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical class CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 claims description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
- 238000002845 discoloration Methods 0.000 claims description 3
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 3
- QQYNRBAAQFZCLF-UHFFFAOYSA-N furan-maleic anhydride adduct Chemical group O1C2C3C(=O)OC(=O)C3C1C=C2 QQYNRBAAQFZCLF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 3
- ROWKCXLLOLDVIO-UHFFFAOYSA-N 7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical group O1C2C=CC1C(C(=O)O)C2C(O)=O ROWKCXLLOLDVIO-UHFFFAOYSA-N 0.000 claims description 2
- KNDQHSIWLOJIGP-UHFFFAOYSA-N 826-62-0 Chemical group C1C2C3C(=O)OC(=O)C3C1C=C2 KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 9
- BSEKZMOBPPOFFB-UHFFFAOYSA-N 3a,4,7,7a-tetrahydro-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical group O1C2C3C(=O)NC(=O)C3C1C=C2 BSEKZMOBPPOFFB-UHFFFAOYSA-N 0.000 claims 1
- 239000002952 polymeric resin Substances 0.000 claims 1
- 229920003002 synthetic resin Polymers 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 26
- 229920005989 resin Polymers 0.000 description 25
- 239000011347 resin Substances 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 239000004816 latex Substances 0.000 description 19
- 229920000126 latex Polymers 0.000 description 19
- 239000008367 deionised water Substances 0.000 description 14
- 229910021641 deionized water Inorganic materials 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000000806 elastomer Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 229920001893 acrylonitrile styrene Polymers 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- -1 cyclic anhydrides Chemical class 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 229920000578 graft copolymer Polymers 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 5
- 230000015271 coagulation Effects 0.000 description 4
- 238000005345 coagulation Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- 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
- IRUDSQHLKGNCGF-UHFFFAOYSA-N 2-methylhex-1-ene Chemical compound CCCCC(C)=C IRUDSQHLKGNCGF-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229960004106 citric acid Drugs 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 229920003244 diene elastomer Polymers 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- HLOUDBQOEJSUPI-UHFFFAOYSA-N 1-ethenyl-2,3-dimethylbenzene Chemical class CC1=CC=CC(C=C)=C1C HLOUDBQOEJSUPI-UHFFFAOYSA-N 0.000 description 1
- QQHQTCGEZWTSEJ-UHFFFAOYSA-N 1-ethenyl-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(C=C)C=C1 QQHQTCGEZWTSEJ-UHFFFAOYSA-N 0.000 description 1
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 1
- FSGHEPDRMHVUCQ-UHFFFAOYSA-N 2-ethoxyprop-1-ene Chemical compound CCOC(C)=C FSGHEPDRMHVUCQ-UHFFFAOYSA-N 0.000 description 1
- YOWQWFMSQCOSBA-UHFFFAOYSA-N 2-methoxypropene Chemical compound COC(C)=C YOWQWFMSQCOSBA-UHFFFAOYSA-N 0.000 description 1
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- FBEDQPGLIKZGIN-UHFFFAOYSA-N 2-methyloct-1-ene Chemical compound CCCCCCC(C)=C FBEDQPGLIKZGIN-UHFFFAOYSA-N 0.000 description 1
- OAOZZYBUAWEDRA-UHFFFAOYSA-N 3,4-dimethylidenehexane Chemical compound CCC(=C)C(=C)CC OAOZZYBUAWEDRA-UHFFFAOYSA-N 0.000 description 1
- CEBRPXLXYCFYGU-UHFFFAOYSA-N 3-methylbut-1-enylbenzene Chemical compound CC(C)C=CC1=CC=CC=C1 CEBRPXLXYCFYGU-UHFFFAOYSA-N 0.000 description 1
- IGLWCQMNTGCUBB-UHFFFAOYSA-N 3-methylidenepent-1-ene Chemical compound CCC(=C)C=C IGLWCQMNTGCUBB-UHFFFAOYSA-N 0.000 description 1
- RYKZRKKEYSRDNF-UHFFFAOYSA-N 3-methylidenepentane Chemical compound CCC(=C)CC RYKZRKKEYSRDNF-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical class CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 241000287462 Phalacrocorax carbo Species 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical class CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 229960002303 citric acid monohydrate Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical class CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical class CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- JAABVEXCGCXWRR-UHFFFAOYSA-N norcantharidin Chemical compound C1CC2C3C(=O)OC(=O)C3C1O2 JAABVEXCGCXWRR-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- GYDSPAVLTMAXHT-UHFFFAOYSA-N pentyl 2-methylprop-2-enoate Chemical class CCCCCOC(=O)C(C)=C GYDSPAVLTMAXHT-UHFFFAOYSA-N 0.000 description 1
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical class CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical class C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical class CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical class CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000008149 soap solution Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1535—Five-membered rings
-
- 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
- C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
- C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/12—Esters; Ether-esters of cyclic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
- C08K5/3417—Five-membered rings condensed with carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/538,569 US3954913A (en) | 1975-01-06 | 1975-01-06 | Stabilized nitrile polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5198755A JPS5198755A (enExample) | 1976-08-31 |
| JPS5946273B2 true JPS5946273B2 (ja) | 1984-11-12 |
Family
ID=24147456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51001100A Expired JPS5946273B2 (ja) | 1975-01-06 | 1976-01-06 | 安定化ニトリル重合体 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3954913A (enExample) |
| JP (1) | JPS5946273B2 (enExample) |
| AT (1) | AT341228B (enExample) |
| BE (1) | BE837310A (enExample) |
| CA (1) | CA1058795A (enExample) |
| CH (1) | CH628914A5 (enExample) |
| DE (1) | DE2559356A1 (enExample) |
| DK (1) | DK2076A (enExample) |
| FR (1) | FR2296665A1 (enExample) |
| GB (1) | GB1495168A (enExample) |
| IT (1) | IT1054717B (enExample) |
| NL (1) | NL7600087A (enExample) |
| SE (1) | SE410196B (enExample) |
| ZA (1) | ZA757811B (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4433086A (en) * | 1981-12-18 | 1984-02-21 | Monsanto Company | Heat stabilized polymers |
| US4415690A (en) * | 1982-05-17 | 1983-11-15 | The Goodyear Tire & Rubber Company | Succinic anhydride derivatives as a scorch inhibitor for carboxylated rubbers |
| US5055520A (en) * | 1988-08-22 | 1991-10-08 | The Standard Oil Company | Blends of high nitrile coploymers and thermoplastic polymers |
| US4914138A (en) * | 1988-08-22 | 1990-04-03 | The Standard Oil Company | Blends of high nitrile polymers and polyolefins and method for the preparation thereon |
| US5114795A (en) * | 1988-10-17 | 1992-05-19 | The Standard Oil Company | Multilayered high barrier packaging materials method for the preparation thereof |
| US5084352A (en) * | 1989-11-15 | 1992-01-28 | The Standard Oil Company | Multilayered barrier structures for packaging |
| CA2125242A1 (en) * | 1993-06-17 | 1994-12-18 | Benedict S. Curatolo | Nonwoven fabrics from high nitrile copolymers |
| US5714535A (en) * | 1993-12-21 | 1998-02-03 | The Standard Oil Company | Stabilizers for high nitrile multipolymers |
| US5981636A (en) * | 1996-12-27 | 1999-11-09 | 3M Innovative Properties Company | Modifying agents for polyolefins |
| AUPP466598A0 (en) * | 1998-07-14 | 1998-08-06 | University Of Newcastle Research Associates Limited, The | Product and process |
| AU772501B2 (en) * | 1998-07-14 | 2004-04-29 | Therappy Pty Limited | Anhydride modified cantharidin analogues useful in the treatment of cancer |
| BR0114041A (pt) | 2000-09-01 | 2004-02-10 | Milliken & Co | Derivados fluorados e alquilados de alditol e composições e artigos de poliolefina contendo os mesmos |
| AUPR392301A0 (en) * | 2001-03-23 | 2001-04-26 | University Of Newcastle Research Associates Limited, The | Protein phosphatase inhibitors |
| US6555696B2 (en) * | 2001-03-23 | 2003-04-29 | Milliken & Company | Asymmetric dipolar multi-substituted alditol derivatives, methods of making thereof, and compositions and articles containing same |
| US6599971B2 (en) * | 2001-03-29 | 2003-07-29 | Milliken & Company | Metals salts of hexahydrophthalic acid as nucleating additives for crystalline thermoplastics |
| US6559211B2 (en) * | 2001-05-23 | 2003-05-06 | Milliken & Company | Highly versatile thermoplastic nucleators |
| US6559216B1 (en) * | 2001-08-21 | 2003-05-06 | Milliken & Company | Low-color ultraviolet absorber compounds and compositions thereof |
| US6602447B2 (en) * | 2001-08-21 | 2003-08-05 | Milliken & Company | Low-color ultraviolet absorbers for high UV wavelength protection applications |
| US6703434B2 (en) * | 2002-04-12 | 2004-03-09 | Milliken & Company | Methods of producing highly nucleated syndiotactic polypropylene |
| AU2003226284A1 (en) * | 2002-04-12 | 2003-10-27 | Milliken And Company | Highly nucleated syndiotactic polypropylene |
| USD516701S1 (en) | 2003-04-11 | 2006-03-07 | Travis Industries, Inc. | Fireplace frame |
| USD507346S1 (en) | 2003-04-11 | 2005-07-12 | Travis Industries, Inc. | Fireplace frame |
| US7094918B2 (en) * | 2003-04-28 | 2006-08-22 | Milliken & Company | Low-color ultraviolet absorbers for thermoplastic and thermoset high UV wavelength protection applications |
| US8870814B2 (en) * | 2003-07-31 | 2014-10-28 | Boston Scientific Scimed, Inc. | Implantable or insertable medical devices containing silicone copolymer for controlled delivery of therapeutic agent |
| US20050038155A1 (en) * | 2003-08-12 | 2005-02-17 | Stephane Berghmans | Thermoplastics exhibiting excellent long-term hydrostatic strength for high-pressure applications |
| US20050038151A1 (en) * | 2003-08-12 | 2005-02-17 | Christopher Kochanowicz | Low density polyethylene articles exhibiting significantly decreased warpage at reduced cooling times |
| US20050038156A1 (en) * | 2003-08-12 | 2005-02-17 | Stephane Berghmans | Polypropylenes exhibiting excellent long-term hydrostatic strength for high-pressure applications |
| US20050038157A1 (en) * | 2003-08-12 | 2005-02-17 | Christopher Kochanowicz | Low density polyethylene articles exhibiting significantly decreased warpage at reduced cooling times |
| US20050046065A1 (en) * | 2003-08-30 | 2005-03-03 | Cowan Martin E. | Thermoplastic fibers exhibiting durable high color strength characteristics |
| US6936650B2 (en) * | 2003-10-03 | 2005-08-30 | Milliken & Company | Nucleating additive formulations of bicyclo[2.2.1]heptane dicarboxylate salts |
| US6946507B2 (en) * | 2003-10-03 | 2005-09-20 | Milliken & Company | Nucleating additive formulations of bicyclo[2.2.1]heptane dicarboxylate salts |
| CN101662939B (zh) | 2007-02-06 | 2015-11-25 | 利克斯特生物技术公司 | 氧杂双环庚烷和氧杂双环庚烯，它们的制备及用途 |
| WO2010147612A1 (en) | 2009-06-18 | 2010-12-23 | Lixte Biotechnology, Inc. | Methods of modulating cell regulation by inhibiting p53 |
| US8227473B2 (en) * | 2008-08-01 | 2012-07-24 | Lixte Biotechnology, Inc. | Oxabicycloheptanes and oxabicycloheptenes, their preparation and use |
| KR101499900B1 (ko) | 2011-12-28 | 2015-03-09 | 삼성전자 주식회사 | 광학필름 및 이를 포함하는 디스플레이 장치 |
| CA2909160C (en) | 2013-04-09 | 2021-05-25 | Lixte Biotechnology, Inc. | Formulations of oxabicycloheptanes and oxabicycloheptenes |
| KR101681427B1 (ko) * | 2014-12-05 | 2016-12-01 | 주식회사 엘지화학 | 열가소성 수지 제조방법 |
| JP7246309B2 (ja) | 2016-12-08 | 2023-03-27 | リクスト・バイオテクノロジー，インコーポレイテッド | 免疫応答を調節するためのオキサビシクロヘプタン |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB582721A (en) * | 1943-12-08 | 1946-11-26 | Distillers Co Yeast Ltd | Improvements in or relating to vinylidene chloride compositions |
| BE502106A (enExample) * | 1950-03-29 | |||
| US2617784A (en) * | 1950-10-26 | 1952-11-11 | Monsanto Chemicals | Acrylonitrile polymers stabilized with a mixture of an aluminum salt and a maleic acid derivative |
| US2661347A (en) * | 1950-10-26 | 1953-12-01 | Monsanto Chemicals | Stabilized acrylonitrile polymers |
| US2868745A (en) * | 1957-01-16 | 1959-01-13 | Harshaw Chem Corp | Vinyl chloride resin stabilized with three component stabilizer |
| US3252936A (en) * | 1962-08-20 | 1966-05-24 | Polymer Corp | Polymer of 3, 3-bis(chloromethyl)oxetane stabilized with methyl cis-3, 6-endomethylene-1, 2, 3, 6-tetrahydrophthalic anhydride |
| US3520847A (en) * | 1966-12-01 | 1970-07-21 | Buna Chem Werke Veb | Stabilized acrylonitrile polymer |
| US3539524A (en) * | 1968-05-15 | 1970-11-10 | Du Pont | Color stabilizer for acrylonitrile polymer |
| GB1318520A (en) * | 1969-11-27 | 1973-05-31 | Ici Ltd | Chemical compositions |
-
1975
- 1975-01-06 US US05/538,569 patent/US3954913A/en not_active Expired - Lifetime
- 1975-12-11 CA CA241,522A patent/CA1058795A/en not_active Expired
- 1975-12-15 ZA ZA757811A patent/ZA757811B/xx unknown
- 1975-12-18 GB GB51812/75A patent/GB1495168A/en not_active Expired
- 1975-12-31 DE DE19752559356 patent/DE2559356A1/de not_active Withdrawn
- 1975-12-31 CH CH1692275A patent/CH628914A5/de not_active IP Right Cessation
-
1976
- 1976-01-05 SE SE7600047A patent/SE410196B/xx not_active IP Right Cessation
- 1976-01-05 BE BE163312A patent/BE837310A/xx unknown
- 1976-01-05 IT IT19038/76A patent/IT1054717B/it active
- 1976-01-05 DK DK2076*#A patent/DK2076A/da unknown
- 1976-01-06 FR FR7600181A patent/FR2296665A1/fr active Granted
- 1976-01-06 NL NL7600087A patent/NL7600087A/xx not_active Application Discontinuation
- 1976-01-06 JP JP51001100A patent/JPS5946273B2/ja not_active Expired
- 1976-01-07 AT AT5876A patent/AT341228B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH628914A5 (de) | 1982-03-31 |
| DK2076A (da) | 1976-07-07 |
| DE2559356A1 (de) | 1976-07-08 |
| GB1495168A (en) | 1977-12-14 |
| NL7600087A (nl) | 1976-07-08 |
| ATA5876A (de) | 1977-05-15 |
| CA1058795A (en) | 1979-07-17 |
| AT341228B (de) | 1978-01-25 |
| FR2296665B1 (enExample) | 1979-05-18 |
| JPS5198755A (enExample) | 1976-08-31 |
| FR2296665A1 (fr) | 1976-07-30 |
| US3954913A (en) | 1976-05-04 |
| AU8745775A (en) | 1977-06-16 |
| BE837310A (fr) | 1976-05-03 |
| SE7600047L (sv) | 1976-07-07 |
| IT1054717B (it) | 1981-11-30 |
| ZA757811B (en) | 1976-11-24 |
| SE410196B (sv) | 1979-10-01 |
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