CA1051451A - Peroxy compounds and vulcanizable compositions thereof - Google Patents
Peroxy compounds and vulcanizable compositions thereofInfo
- Publication number
- CA1051451A CA1051451A CA254,921A CA254921A CA1051451A CA 1051451 A CA1051451 A CA 1051451A CA 254921 A CA254921 A CA 254921A CA 1051451 A CA1051451 A CA 1051451A
- Authority
- CA
- Canada
- Prior art keywords
- carbons
- alkyl
- dimethyl
- butyl
- butylperoxy
- 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
- 239000000203 mixture Substances 0.000 title claims description 57
- 125000000864 peroxy group Chemical group O(O*)* 0.000 title description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- -1 peroxy compound Chemical class 0.000 claims description 46
- 229920000642 polymer Polymers 0.000 claims description 24
- 238000004132 cross linking Methods 0.000 claims description 23
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 229920001971 elastomer Polymers 0.000 claims description 14
- 229920000181 Ethylene propylene rubber Polymers 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229920003225 polyurethane elastomer Polymers 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000011872 intimate mixture Substances 0.000 claims description 6
- 239000005060 rubber Substances 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 5
- 238000013007 heat curing Methods 0.000 claims description 5
- 229920001225 polyester resin Polymers 0.000 claims description 5
- 239000004645 polyester resin Substances 0.000 claims description 5
- ZSKZKQYMOFWSIZ-UHFFFAOYSA-N (4-ethoxycarbonyloxy-2-methylpentan-2-yl)oxy ethyl carbonate Chemical compound CCOC(=O)OOC(C)(C)CC(C)OC(=O)OCC ZSKZKQYMOFWSIZ-UHFFFAOYSA-N 0.000 claims description 4
- SUCCBPGZGSYEIY-UHFFFAOYSA-N (4-tert-butylperoxy-4-methylpentan-2-yl) n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC(C)CC(C)(C)OOC(C)(C)C SUCCBPGZGSYEIY-UHFFFAOYSA-N 0.000 claims description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
- ZICCCVLQGURNBD-UHFFFAOYSA-N butyl (4-tert-butylperoxy-4-methylpentan-2-yl) carbonate Chemical compound CCCCOC(=O)OC(C)CC(C)(C)OOC(C)(C)C ZICCCVLQGURNBD-UHFFFAOYSA-N 0.000 claims description 4
- KSUIUIIRUMQYJT-UHFFFAOYSA-N butyl (7-tert-butylperoxy-3,7-dimethyloctyl) carbonate Chemical compound CCCCOC(=O)OCCC(C)CCCC(C)(C)OOC(C)(C)C KSUIUIIRUMQYJT-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229920003052 natural elastomer Polymers 0.000 claims description 3
- 229920001194 natural rubber Polymers 0.000 claims description 3
- 229920001187 thermosetting polymer Polymers 0.000 claims description 3
- 244000043261 Hevea brasiliensis Species 0.000 claims description 2
- 229920000459 Nitrile rubber Polymers 0.000 claims description 2
- SWFWJQASKPQHCW-UHFFFAOYSA-N [4-(cyclohexylcarbamoylperoxy)-4-methylpentan-2-yl] n-cyclohexylcarbamate Chemical compound C1CCCCC1NC(=O)OC(C)CC(C)(C)OOC(=O)NC1CCCCC1 SWFWJQASKPQHCW-UHFFFAOYSA-N 0.000 claims description 2
- 229920001684 low density polyethylene Polymers 0.000 claims description 2
- 239000004702 low-density polyethylene Substances 0.000 claims description 2
- 229920002379 silicone rubber Polymers 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- QRMWBQXFPSDNCS-UHFFFAOYSA-N (4-tert-butylperoxy-4-methylpentan-2-yl) n-methylcarbamate Chemical compound CNC(=O)OC(C)CC(C)(C)OOC(C)(C)C QRMWBQXFPSDNCS-UHFFFAOYSA-N 0.000 claims 1
- 239000011243 crosslinked material Substances 0.000 claims 1
- 239000005038 ethylene vinyl acetate Substances 0.000 claims 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims 1
- 239000004945 silicone rubber Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 21
- 125000000304 alkynyl group Chemical group 0.000 abstract description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical class NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 238000009472 formulation Methods 0.000 description 23
- 239000000243 solution Substances 0.000 description 17
- 150000002978 peroxides Chemical class 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000001723 curing Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000004698 Polyethylene Substances 0.000 description 8
- 239000006229 carbon black Substances 0.000 description 8
- 235000019241 carbon black Nutrition 0.000 description 8
- 239000000806 elastomer Substances 0.000 description 8
- 229920000573 polyethylene Polymers 0.000 description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 6
- 239000003431 cross linking reagent Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- JNSWFNBIZLIBPH-UHFFFAOYSA-N 4-tert-butylperoxy-4-methylpentan-2-ol Chemical compound CC(O)CC(C)(C)OOC(C)(C)C JNSWFNBIZLIBPH-UHFFFAOYSA-N 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 238000007906 compression Methods 0.000 description 5
- 230000006835 compression Effects 0.000 description 5
- SVTBMSDMJJWYQN-UHFFFAOYSA-N hexylene glycol Natural products CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000010058 rubber compounding Methods 0.000 description 4
- 239000011975 tartaric acid Substances 0.000 description 4
- 235000002906 tartaric acid Nutrition 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000006242 Semi-Reinforcing Furnace Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 229940051250 hexylene glycol Drugs 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920002689 polyvinyl acetate Polymers 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- NKTDTMONXHODTI-UHFFFAOYSA-N 2-pentyne Chemical compound CCC#CC NKTDTMONXHODTI-UHFFFAOYSA-N 0.000 description 2
- OIXFWERBTHZQQH-UHFFFAOYSA-N 4-hydroperoxy-4-methylpentan-2-ol Chemical class CC(O)CC(C)(C)OO OIXFWERBTHZQQH-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 2
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- PSXRWZBTVAZNSF-UHFFFAOYSA-N hydron;quinoline;chloride Chemical compound Cl.N1=CC=CC2=CC=CC=C21 PSXRWZBTVAZNSF-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
- 239000001095 magnesium carbonate Substances 0.000 description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 239000012779 reinforcing material Substances 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000005061 synthetic rubber Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BGBZKIRHOGDVJB-UHFFFAOYSA-N (4-carbonochloridoyloxy-2-methylpentan-2-yl)oxy ethyl carbonate Chemical compound CCOC(=O)OOC(C)(C)CC(C)OC(Cl)=O BGBZKIRHOGDVJB-UHFFFAOYSA-N 0.000 description 1
- RIDIOBMUXMBOLL-UHFFFAOYSA-N (4-tert-butylperoxy-4-methylpent-2-ynyl) ethyl carbonate Chemical compound CCOC(=O)OCC#CC(C)(C)OOC(C)(C)C RIDIOBMUXMBOLL-UHFFFAOYSA-N 0.000 description 1
- XBJCCMSXWGQDBJ-UHFFFAOYSA-N (4-tert-butylperoxy-4-methylpentan-2-yl) carbamate Chemical compound NC(=O)OC(C)CC(C)(C)OOC(C)(C)C XBJCCMSXWGQDBJ-UHFFFAOYSA-N 0.000 description 1
- VSRWNXSMMZZTLV-UHFFFAOYSA-N (4-tert-butylperoxy-4-methylpentan-2-yl) carbonochloridate Chemical compound ClC(=O)OC(C)CC(C)(C)OOC(C)(C)C VSRWNXSMMZZTLV-UHFFFAOYSA-N 0.000 description 1
- DOQLDMMDPJHYLG-UHFFFAOYSA-N (4-tert-butylperoxy-4-methylpentyl) n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OCCCC(C)(C)OOC(C)(C)C DOQLDMMDPJHYLG-UHFFFAOYSA-N 0.000 description 1
- QUQIFOCLJMDVEF-UHFFFAOYSA-N (5-tert-butylperoxy-5-methylhexan-2-yl) propan-2-yl carbonate Chemical compound CC(C)OC(=O)OC(C)CCC(C)(C)OOC(C)(C)C QUQIFOCLJMDVEF-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- QBEPGEFCSVHQAP-UHFFFAOYSA-N 2-methylocta-3,5-diyne-2,7-diol Chemical compound CC(O)C#CC#CC(C)(C)O QBEPGEFCSVHQAP-UHFFFAOYSA-N 0.000 description 1
- LVFZPPKYRHKSHP-UHFFFAOYSA-N 2-methyloctane-2,4-diol Chemical compound CCCCC(O)CC(C)(C)O LVFZPPKYRHKSHP-UHFFFAOYSA-N 0.000 description 1
- NXYNNUOWSFTLTO-UHFFFAOYSA-N 4-butyloctane-2,4-diol Chemical compound CCCCC(O)(CC(C)O)CCCC NXYNNUOWSFTLTO-UHFFFAOYSA-N 0.000 description 1
- OOGHWMQZSAAEFV-UHFFFAOYSA-N 4-methyloctane-2,4-diol Chemical compound CCCCC(C)(O)CC(C)O OOGHWMQZSAAEFV-UHFFFAOYSA-N 0.000 description 1
- YJGBAXHVTNTDNV-UHFFFAOYSA-N 7-hydroperoxy-3,7-dimethyloctan-1-ol Chemical compound OCCC(C)CCCC(C)(C)OO YJGBAXHVTNTDNV-UHFFFAOYSA-N 0.000 description 1
- QYVSIFRJFVQTPG-UHFFFAOYSA-N 9-methyldecane-1,9-diol Chemical compound CC(C)(O)CCCCCCCCO QYVSIFRJFVQTPG-UHFFFAOYSA-N 0.000 description 1
- 229920001342 Bakelite® Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000006238 High Abrasion Furnace Substances 0.000 description 1
- FPCCDPXRNNVUOM-UHFFFAOYSA-N Hydroxycitronellol Chemical compound OCCC(C)CCCC(C)(C)O FPCCDPXRNNVUOM-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- FMGUJLASXUBMOP-UHFFFAOYSA-N N-Methyl-N,4-dinitrosoaniline Chemical compound O=NN(C)C1=CC=C(N=O)C=C1 FMGUJLASXUBMOP-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 241001163743 Perlodes 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
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FLQHCOBZYQIDBO-UHFFFAOYSA-N [4-(dimethylcarbamoylperoxy)-4-methylpent-2-ynyl] n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OCC#CC(C)(C)OOC(=O)N(C)C FLQHCOBZYQIDBO-UHFFFAOYSA-N 0.000 description 1
- ZXRKXFRBFNMZDY-UHFFFAOYSA-N [4-(dimethylcarbamoylperoxy)-4-methylpentan-2-yl] n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC(C)CC(C)(C)OOC(=O)N(C)C ZXRKXFRBFNMZDY-UHFFFAOYSA-N 0.000 description 1
- DCMBOBUYPCYWBI-UHFFFAOYSA-N [4-methyl-4-(2,4,4-trimethylpentan-2-ylperoxy)pentan-2-yl] n-cyclopentylcarbamate Chemical compound CC(C)(C)CC(C)(C)OOC(C)(C)CC(C)OC(=O)NC1CCCC1 DCMBOBUYPCYWBI-UHFFFAOYSA-N 0.000 description 1
- LEJQFABZSAINMM-UHFFFAOYSA-N [6-(dimethylcarbamoylperoxy)-4,4,6-trimethylheptan-2-yl] n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC(C)CC(C)(C)CC(C)(C)OOC(=O)N(C)C LEJQFABZSAINMM-UHFFFAOYSA-N 0.000 description 1
- BIWNXJCHRJVMSU-UHFFFAOYSA-N [9-methyl-9-[(4,6,6-trimethyl-4-bicyclo[3.1.1]heptanyl)peroxy]decyl] n,n-dibutylcarbamate Chemical compound CCCCN(CCCC)C(=O)OCCCCCCCCC(C)(C)OOC1(C)CCC2C(C)(C)C1C2 BIWNXJCHRJVMSU-UHFFFAOYSA-N 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 239000004637 bakelite Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 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
- MZWPUQMAMJFJPQ-UHFFFAOYSA-N butyl n,n-dimethylcarbamate Chemical compound CCCCOC(=O)N(C)C MZWPUQMAMJFJPQ-UHFFFAOYSA-N 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- UYMQGIDIEUCSBT-UHFFFAOYSA-N hexane-1,6-diol hydrogen peroxide Chemical compound OO.OCCCCCCO UYMQGIDIEUCSBT-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- LILZEAJBVQOINI-UHFFFAOYSA-N octa-3,5-diyne Chemical compound CCC#CC#CCC LILZEAJBVQOINI-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- MMCOUVMKNAHQOY-UHFFFAOYSA-L oxido carbonate Chemical compound [O-]OC([O-])=O MMCOUVMKNAHQOY-UHFFFAOYSA-L 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 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
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000004636 vulcanized rubber Substances 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
- C08K5/14—Peroxides
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/40—Peroxy compounds containing nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/596,778 US4129700A (en) | 1975-07-17 | 1975-07-17 | Peroxy compounds and vulcanizable compositions thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1051451A true CA1051451A (en) | 1979-03-27 |
Family
ID=24388657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA254,921A Expired CA1051451A (en) | 1975-07-17 | 1976-06-16 | Peroxy compounds and vulcanizable compositions thereof |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4129700A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5212130A (cg-RX-API-DMAC7.html) |
| AU (1) | AU508804B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA1051451A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2631911A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1511102A (cg-RX-API-DMAC7.html) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4180518A (en) * | 1975-07-17 | 1979-12-25 | Pennwalt Corporation | Peroxy compounds |
| US4218548A (en) * | 1978-08-28 | 1980-08-19 | Pennwalt Corporation | Peroxy compounds and vulcanizable compositions thereof |
| US4525308A (en) * | 1983-05-20 | 1985-06-25 | Pennwalt Corporation | Hydroxy-t-alkyl peroxyesters |
| US5475072A (en) * | 1994-02-09 | 1995-12-12 | Elf Atochem North America, Inc. | Unsaturated peroxide compositions, polymeric-peroxides derived therefrom and their uses |
| US7872075B2 (en) * | 2005-10-07 | 2011-01-18 | Exxonmobil Chemical Patents Inc. | Peroxide-cured thermoplastic vulcanizates and process for making the same |
| US20070244264A1 (en) * | 2006-04-14 | 2007-10-18 | Granger James E | Process and apparatus for preparation of thermoplastic polymer blends |
| ES3016647T3 (en) * | 2014-12-09 | 2025-05-09 | Arkema Inc | Compositions and methods for crosslinking polymers in the presence of atmospheric oxygen |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL252162A (cg-RX-API-DMAC7.html) * | 1959-06-01 | |||
| BE627014A (cg-RX-API-DMAC7.html) * | 1962-01-12 | |||
| US3264274A (en) * | 1963-11-18 | 1966-08-02 | U S Peroxygen Corp | Diperesters of polyols |
| US3671651A (en) * | 1968-05-07 | 1972-06-20 | Pennwalt Corp | Peroxy compounds containing a haloformate group |
| US3725455A (en) * | 1968-06-17 | 1973-04-03 | Pennwalt Corp | Peroxy compounds containing a carbonate group |
| US3839390A (en) * | 1968-07-17 | 1974-10-01 | Pennwalt Corp | Polyperoxides affording sequential free radical generation |
| US3706818A (en) * | 1968-07-17 | 1972-12-19 | Pennwalt Corp | Processes using polyperoxides affording sequential free radical generation |
| US3879353A (en) * | 1971-09-01 | 1975-04-22 | Owens Illinois Inc | Linear copolymers having pendant peroxycarbonate ester functionality, their synthesis and use |
-
1975
- 1975-07-17 US US05/596,778 patent/US4129700A/en not_active Expired - Lifetime
-
1976
- 1976-06-16 CA CA254,921A patent/CA1051451A/en not_active Expired
- 1976-06-18 GB GB25397/76A patent/GB1511102A/en not_active Expired
- 1976-06-25 AU AU15291/76A patent/AU508804B2/en not_active Expired
- 1976-07-12 JP JP51082051A patent/JPS5212130A/ja active Granted
- 1976-07-15 DE DE19762631911 patent/DE2631911A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6121945B2 (cg-RX-API-DMAC7.html) | 1986-05-29 |
| JPS5212130A (en) | 1977-01-29 |
| US4129700A (en) | 1978-12-12 |
| AU1529176A (en) | 1978-01-05 |
| AU508804B2 (en) | 1980-04-03 |
| GB1511102A (en) | 1978-05-17 |
| DE2631911A1 (de) | 1977-02-03 |
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