CA1093090A - Non-migratory sulfonyl azide antioxidants - Google Patents
Non-migratory sulfonyl azide antioxidantsInfo
- Publication number
- CA1093090A CA1093090A CA263,930A CA263930A CA1093090A CA 1093090 A CA1093090 A CA 1093090A CA 263930 A CA263930 A CA 263930A CA 1093090 A CA1093090 A CA 1093090A
- Authority
- CA
- Canada
- Prior art keywords
- antioxidant
- polymer
- product
- butyl
- hydroxyphenyl
- 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
- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 89
- HSVFKFNNMLUVEY-UHFFFAOYSA-N sulfuryl diazide Chemical compound [N-]=[N+]=NS(=O)(=O)N=[N+]=[N-] HSVFKFNNMLUVEY-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 229920000642 polymer Polymers 0.000 claims abstract description 46
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 230000003078 antioxidant effect Effects 0.000 claims description 71
- 238000000034 method Methods 0.000 claims description 50
- -1 polyethylene Polymers 0.000 claims description 42
- 229920001971 elastomer Polymers 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 238000000605 extraction Methods 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 229920000459 Nitrile rubber Polymers 0.000 claims description 10
- 239000004698 Polyethylene Substances 0.000 claims description 10
- 239000000806 elastomer Substances 0.000 claims description 10
- 229920000573 polyethylene Polymers 0.000 claims description 10
- 239000004743 Polypropylene Substances 0.000 claims description 9
- 230000006866 deterioration Effects 0.000 claims description 8
- 230000001590 oxidative effect Effects 0.000 claims description 8
- 229920001155 polypropylene Polymers 0.000 claims description 8
- 244000043261 Hevea brasiliensis Species 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 229920003052 natural elastomer Polymers 0.000 claims description 5
- 229920001194 natural rubber Polymers 0.000 claims description 5
- 229920001169 thermoplastic Polymers 0.000 claims description 5
- 239000004416 thermosoftening plastic Substances 0.000 claims description 5
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 4
- 125000006177 alkyl benzyl group Chemical group 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000004073 vulcanization Methods 0.000 claims description 3
- HRYZDZKHGNHTEX-UHFFFAOYSA-N (4-azidosulfonylphenyl)-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]carbamic acid Chemical group CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)CN(C2=CC=C(C=C2)S(=O)(=O)N=[N+]=[N-])C(=O)O HRYZDZKHGNHTEX-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical group C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 238000007493 shaping process Methods 0.000 claims description 2
- 229920001897 terpolymer Polymers 0.000 claims description 2
- BCCTUWRIXLFYOF-UHFFFAOYSA-N 1-(4-azidosulfonylphenyl)-3-[2-(3,5-ditert-butyl-4-hydroxyphenyl)ethyl]urea Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCNC(=O)NC=2C=CC(=CC=2)S(=O)(=O)N=[N+]=[N-])=C1 BCCTUWRIXLFYOF-UHFFFAOYSA-N 0.000 claims 2
- KGTPAYDNQNALGG-UHFFFAOYSA-N 2-[(4-azidosulfonylphenyl)carbamoyloxy]ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound C(C)(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)CCC(=O)OCCOC(NC1=CC=C(C=C1)S(=O)(=O)N=[N+]=[N-])=O KGTPAYDNQNALGG-UHFFFAOYSA-N 0.000 claims 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 229920005992 thermoplastic resin Polymers 0.000 claims 1
- 230000001617 migratory effect Effects 0.000 abstract description 2
- 235000006708 antioxidants Nutrition 0.000 description 49
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 35
- 239000004202 carbamide Substances 0.000 description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 229920002943 EPDM rubber Polymers 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 125000001624 naphthyl group Chemical group 0.000 description 7
- 239000005060 rubber Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000000638 solvent extraction Methods 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- HNURKXXMYARGAY-UHFFFAOYSA-N 2,6-Di-tert-butyl-4-hydroxymethylphenol Chemical compound CC(C)(C)C1=CC(CO)=CC(C(C)(C)C)=C1O HNURKXXMYARGAY-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000012612 commercial material Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- SZAYCXAISBIYKQ-UHFFFAOYSA-N n-diazo-4-isocyanatobenzenesulfonamide Chemical compound [N-]=[N+]=NS(=O)(=O)C1=CC=C(N=C=O)C=C1 SZAYCXAISBIYKQ-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
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 2
- 229920013639 polyalphaolefin Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- QADSNZODNLCBJW-UHFFFAOYSA-N (4-azidosulfonylphenyl)urea Chemical compound N(=[N+]=[N-])S(=O)(=O)C1=CC=C(C=C1)NC(=O)N QADSNZODNLCBJW-UHFFFAOYSA-N 0.000 description 1
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- OMRHAXXAPQQSDP-UHFFFAOYSA-N 1-(4-azidosulfonylphenyl)-3-(3,5-ditert-butyl-4-hydroxyphenyl)urea Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(=CC=2)S(=O)(=O)N=[N+]=[N-])=C1 OMRHAXXAPQQSDP-UHFFFAOYSA-N 0.000 description 1
- HCLIPLOYBQFYJS-UHFFFAOYSA-N 1-(4-azidosulfonylphenyl)-3-[2-(3-ethyl-4-hydroxy-5-propan-2-ylphenyl)ethyl]urea Chemical compound CC(C)C1=C(O)C(CC)=CC(CCNC(=O)NC=2C=CC(=CC=2)S(=O)(=O)N=[N+]=[N-])=C1 HCLIPLOYBQFYJS-UHFFFAOYSA-N 0.000 description 1
- LWWJCBWPMSBTLO-UHFFFAOYSA-N 1-(4-azidosulfonylphenyl)-3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propyl]urea Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCCNC(=O)NC=2C=CC(=CC=2)S(=O)(=O)N=[N+]=[N-])=C1 LWWJCBWPMSBTLO-UHFFFAOYSA-N 0.000 description 1
- CEOSGTLSHOIFDU-UHFFFAOYSA-N 1-(4-azidosulfonylphenyl)-3-[3-(4-hydroxy-3,5-dimethylphenyl)propyl]urea Chemical compound CC1=C(O)C(C)=CC(CCCNC(=O)NC=2C=CC(=CC=2)S(=O)(=O)N=[N+]=[N-])=C1 CEOSGTLSHOIFDU-UHFFFAOYSA-N 0.000 description 1
- WRHHMQCZIXEKRQ-UHFFFAOYSA-N 1-(5-amino-2-azidosulfonylphenyl)-3-(3-benzyl-4-hydroxy-5-octylphenyl)urea Chemical compound C=1C(CC=2C=CC=CC=2)=C(O)C(CCCCCCCC)=CC=1NC(=O)NC1=CC(N)=CC=C1S(=O)(=O)N=[N+]=[N-] WRHHMQCZIXEKRQ-UHFFFAOYSA-N 0.000 description 1
- QFEVGTCQTZXXIQ-UHFFFAOYSA-N 1-[4,5-bis(azidosulfonyl)pentyl]-3-(3-butan-2-yl-4-hydroxy-5-octylphenyl)urea Chemical compound CCCCCCCCC1=CC(NC(=O)NCCCC(CS(=O)(=O)N=[N+]=[N-])S(=O)(=O)N=[N+]=[N-])=CC(C(C)CC)=C1O QFEVGTCQTZXXIQ-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- FJSNTQXNQNSZJS-UHFFFAOYSA-N 2-(2-nonanoyloxypropoxy)propyl nonanoate Chemical compound CCCCCCCCC(=O)OCC(C)OCC(C)OC(=O)CCCCCCCC FJSNTQXNQNSZJS-UHFFFAOYSA-N 0.000 description 1
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 1
- BQZBRTGAAYHAJJ-UHFFFAOYSA-N 2-[(3-dodecyl-4-hydroxy-5-methylphenyl)methoxy]ethyl N-(4-azidosulfonylphenyl)carbamate Chemical compound CC=1C=C(COCCOC(NC2=CC=C(C=C2)S(=O)(=O)N=[N+]=[N-])=O)C=C(C=1O)CCCCCCCCCCCC BQZBRTGAAYHAJJ-UHFFFAOYSA-N 0.000 description 1
- HKJZHAHOGHUWRR-UHFFFAOYSA-N 2-[[4-hydroxy-3,5-bis(2-methylbutan-2-yl)phenyl]methoxy]ethyl N-(4-azidosulfonylphenyl)carbamate Chemical compound C(C)(C)(CC)C=1C=C(COCCOC(NC2=CC=C(C=C2)S(=O)(=O)N=[N+]=[N-])=O)C=C(C=1O)C(C)(C)CC HKJZHAHOGHUWRR-UHFFFAOYSA-N 0.000 description 1
- CKOJVSKGNQZKPM-UHFFFAOYSA-N 2-azidosulfonylethylurea Chemical compound N(=[N+]=[N-])S(=O)(=O)CCNC(N)=O CKOJVSKGNQZKPM-UHFFFAOYSA-N 0.000 description 1
- ZXUKNOGFRSOORK-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyl chloride Chemical compound CC(C)(C)C1=CC(CCC(Cl)=O)=CC(C(C)(C)C)=C1O ZXUKNOGFRSOORK-UHFFFAOYSA-N 0.000 description 1
- BUZICZZQJDLXJN-UHFFFAOYSA-N 3-azaniumyl-4-hydroxybutanoate Chemical compound OCC(N)CC(O)=O BUZICZZQJDLXJN-UHFFFAOYSA-N 0.000 description 1
- XTHVCBDFFSYMJK-UHFFFAOYSA-N 3-azidosulfonylpropyl-[(3-benzyl-4-hydroxy-5-octan-2-ylphenyl)methyl]carbamic acid Chemical compound CCCCCCC(C)C1=CC(=CC(=C1O)CC2=CC=CC=C2)CN(CCCS(=O)(=O)N=[N+]=[N-])C(=O)O XTHVCBDFFSYMJK-UHFFFAOYSA-N 0.000 description 1
- CILJFWAVBOBXJO-UHFFFAOYSA-N 4-[3,5-di(butan-2-yl)-4-hydroxyphenyl]butyl N-(4-azidosulfonylbutyl)carbamate Chemical compound CCC(C)C1=CC(CCCCOC(=O)NCCCCS(=O)(=O)N=[N+]=[N-])=CC(C(C)CC)=C1O CILJFWAVBOBXJO-UHFFFAOYSA-N 0.000 description 1
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- PUXGCFRABSKGED-UHFFFAOYSA-N 4-isocyanatobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(N=C=O)C=C1 PUXGCFRABSKGED-UHFFFAOYSA-N 0.000 description 1
- AOEHSBYMVWRBMC-UHFFFAOYSA-N 5-(2-ethylhexanoyloxy)pentyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OCCCCCOC(=O)C(CC)CCCC AOEHSBYMVWRBMC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical group CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 description 1
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- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
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- 125000000746 allylic group Chemical group 0.000 description 1
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- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- ZDWGXBPVPXVXMQ-UHFFFAOYSA-N bis(2-ethylhexyl) nonanedioate Chemical compound CCCCC(CC)COC(=O)CCCCCCCC(=O)OCC(CC)CCCC ZDWGXBPVPXVXMQ-UHFFFAOYSA-N 0.000 description 1
- KGYOGHGWJJGZMW-UHFFFAOYSA-N bis(3,5,5-trimethylhexyl) pentanedioate Chemical compound CC(C)(C)CC(C)CCOC(=O)CCCC(=O)OCCC(C)CC(C)(C)C KGYOGHGWJJGZMW-UHFFFAOYSA-N 0.000 description 1
- HIEOGLNFUKBFCF-UHFFFAOYSA-N bis(3-methylbutyl) hexanedioate Chemical compound CC(C)CCOC(=O)CCCCC(=O)OCCC(C)C HIEOGLNFUKBFCF-UHFFFAOYSA-N 0.000 description 1
- SKKTUOZKZKCGTB-UHFFFAOYSA-N butyl carbamate Chemical compound CCCCOC(N)=O SKKTUOZKZKCGTB-UHFFFAOYSA-N 0.000 description 1
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- 239000004359 castor oil Substances 0.000 description 1
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- 235000012716 cod liver oil Nutrition 0.000 description 1
- 239000003026 cod liver oil Substances 0.000 description 1
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- 239000002385 cottonseed oil Substances 0.000 description 1
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- 239000002173 cutting fluid Substances 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- MJOKHGMXPJXFTG-UHFFFAOYSA-N dihexyl nonanedioate Chemical compound CCCCCCOC(=O)CCCCCCCC(=O)OCCCCCC MJOKHGMXPJXFTG-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
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- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- DPUXQWOMYBMHRN-UHFFFAOYSA-N hexa-2,3-diene Chemical compound CCC=C=CC DPUXQWOMYBMHRN-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000000266 injurious effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 1
- YNTOKMNHRPSGFU-UHFFFAOYSA-N n-Propyl carbamate Chemical compound CCCOC(N)=O YNTOKMNHRPSGFU-UHFFFAOYSA-N 0.000 description 1
- RMBCQVQFRYIMFN-UHFFFAOYSA-N naphthalen-1-yl carbamate Chemical compound C1=CC=C2C(OC(=O)N)=CC=CC2=C1 RMBCQVQFRYIMFN-UHFFFAOYSA-N 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000001993 wax 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/43—Compounds containing sulfur bound to nitrogen
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/28—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen, oxygen and sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US708,676 | 1976-07-26 | ||
| US05/708,676 US4031068A (en) | 1976-07-26 | 1976-07-26 | Non-migratory sulfonyl azide antioxidants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1093090A true CA1093090A (en) | 1981-01-06 |
Family
ID=24846757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA263,930A Expired CA1093090A (en) | 1976-07-26 | 1976-10-22 | Non-migratory sulfonyl azide antioxidants |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4031068A (Direct) |
| JP (1) | JPS5831342B2 (Direct) |
| CA (1) | CA1093090A (Direct) |
| DE (1) | DE2733657A1 (Direct) |
| FR (1) | FR2359820A1 (Direct) |
| GB (1) | GB1583652A (Direct) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5080058A (Direct) * | 1973-11-13 | 1975-06-28 | ||
| US4268450A (en) * | 1977-08-08 | 1981-05-19 | Rockwell International Corporation | Energetic hydroxy-terminated azido polymer |
| US4221872A (en) * | 1977-11-28 | 1980-09-09 | Ici Australia Limited | Process for removing unsaturation from ion exchange resins containing unquaternized amino groups by hydrogenation with imine |
| JPS5752271A (en) * | 1980-11-12 | 1982-03-27 | Sanyo Electric Co Ltd | Horizontal synchronizing circuit |
| US4549824A (en) * | 1983-12-30 | 1985-10-29 | International Business Machines Corporation | Ink additives for efficient thermal ink transfer printing processes |
| DE3404456A1 (de) * | 1984-02-08 | 1985-08-08 | Plüss-Staufer AG, Oftringen, Aargau | Kupplungsmittel zwischen mineralischen fuellstoffen und polymeren |
| US4579898A (en) * | 1984-12-24 | 1986-04-01 | Mobil Oil Corporation | Linear polyethylenes stabilized against melt index drop with aromatic sulfonhydrazides |
| US4636861A (en) * | 1985-04-01 | 1987-01-13 | Rca Corporation | Two-loop line deflection system |
| GB8928963D0 (en) * | 1989-12-21 | 1990-02-28 | Shell Int Research | Lubricating oil compositions and their preparation |
| US5955550A (en) * | 1994-01-25 | 1999-09-21 | Exxon Chemical Patents, Inc. | Polymeric vehicle for providing solventless coating compositions |
| US5969085A (en) * | 1994-01-25 | 1999-10-19 | Exxon Chemical Patents, Inc. | Polymeric vehicle for high solids coatings |
| US5910563A (en) * | 1994-01-25 | 1999-06-08 | Exxon Chemical Patents, Inc. | Water thinned polymeric vehicle for coating compositions with low amounts of volatile organic compounds |
| US5973072A (en) * | 1996-03-21 | 1999-10-26 | Exxon Chemical Patents, Inc. | Polymeric vehicles which include a phenolic urethane reactive diluent |
| US6103826A (en) * | 1995-04-19 | 2000-08-15 | Eastern Michigan University | Clearcoat compositions containing phenolic ester compounds |
| US6051674A (en) * | 1996-08-26 | 2000-04-18 | Exxon Chemical Patents, Inc. | Polymeric vehicles which include a phenol blocked isocyanate having aliphatic hydroxyl fucntionality |
| US5681906A (en) * | 1995-04-19 | 1997-10-28 | Exxon Chemical Patents Inc. | Thermoset coating compositions having improved hardness |
| WO1997006129A1 (en) * | 1995-08-09 | 1997-02-20 | Exxon Chemical Patents, Inc. | Polymeric vehicles which include a phenolic urethane reactive diluent |
| US5817722A (en) * | 1995-10-10 | 1998-10-06 | Exxon Chemical Patents Inc. | Low viscosity, high solids polyesterdiols and compositions containing same |
| US6005135A (en) * | 1996-03-21 | 1999-12-21 | Exxon Chemical Patents Inc. | Water-borne polymeric vehicle for coating compositions containing an amine or ammonium salt of phenolic ester alcohols |
| ES2127684B1 (es) * | 1996-05-31 | 2000-02-16 | Consejo Superior Investigacion | Procedimiento para promover la union quimica entre elastomeros y negros de carbono mediante derivados de benceno sulfonil azidas. |
| WO2001083605A2 (en) * | 2000-05-04 | 2001-11-08 | Dow Global Technologies Inc. | Molecular melt and methods for making and using the molecular melt |
| WO2001092403A2 (en) * | 2000-05-26 | 2001-12-06 | Dow Global Technologies Inc. | Polyethylene rich/polypropylene blends and their uses |
| WO2003040229A1 (en) * | 2001-11-02 | 2003-05-15 | Dow Global Technologies Inc. | Molecular melt and methods for making and using the molecular melt |
| ES2332139T3 (es) * | 2005-11-23 | 2010-01-27 | F. Hoffmann-La Roche Ag | Polinucleotidos con mimetico de fosfato. |
| KR20130114119A (ko) | 2010-09-03 | 2013-10-16 | 포르마 티엠, 엘엘씨. | Ｎａｍｐｔ의 억제를 위한 신규 화합물 및 조성물 |
| CN105705563B (zh) * | 2013-11-07 | 2018-03-23 | 阿克苏诺贝尔化学品国际有限公司 | 用于改性乙烯系聚合物和共聚物的方法 |
| CN107107547B (zh) | 2014-12-30 | 2019-11-01 | 陶氏环球技术有限责任公司 | 用于连接层的磺酰叠氮化物衍生物 |
| US10183924B2 (en) | 2015-12-30 | 2019-01-22 | Dow Global Technologies Llc | Sulfonylazide derivative for diene polymer |
| TWI746568B (zh) | 2016-06-23 | 2021-11-21 | 美商陶氏全球科技有限責任公司 | 磺醯疊氮酸酐之製造 |
| TWI750182B (zh) | 2016-06-23 | 2021-12-21 | 美商陶氏全球科技有限責任公司 | 用於連接層之脂族磺醯疊氮酸酐 |
| KR102603998B1 (ko) * | 2021-11-22 | 2023-11-17 | 세종대학교산학협력단 | 유기물에 공유결합으로 연결되는 산화방지제 및 그의 제조방법 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE622066A (Direct) * | 1961-03-15 | |||
| US3284421A (en) * | 1962-02-12 | 1966-11-08 | Hercules Inc | Modifying polymers |
| US3298975A (en) * | 1966-03-18 | 1967-01-17 | Hercules Inc | Expandable partially-foamed and cured polypropylene composition |
| US3652599A (en) * | 1970-03-02 | 1972-03-28 | Upjohn Co | Novel azidosulfonylcarbanilates |
| US3859261A (en) * | 1971-06-08 | 1975-01-07 | Hercules Inc | Azides |
| US3763118A (en) * | 1972-04-24 | 1973-10-02 | Upjohn Co | Novel compositions |
| US3991131A (en) * | 1976-03-15 | 1976-11-09 | The Goodyear Tire & Rubber Company | Azidoformyl antioxidants |
-
1976
- 1976-07-26 US US05/708,676 patent/US4031068A/en not_active Expired - Lifetime
- 1976-10-22 CA CA263,930A patent/CA1093090A/en not_active Expired
-
1977
- 1977-07-25 FR FR7722804A patent/FR2359820A1/fr active Granted
- 1977-07-26 JP JP52089695A patent/JPS5831342B2/ja not_active Expired
- 1977-07-26 GB GB31288/77A patent/GB1583652A/en not_active Expired
- 1977-07-26 DE DE19772733657 patent/DE2733657A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| FR2359820A1 (fr) | 1978-02-24 |
| GB1583652A (en) | 1981-01-28 |
| JPS5831342B2 (ja) | 1983-07-05 |
| DE2733657A1 (de) | 1978-02-02 |
| JPS5315335A (en) | 1978-02-13 |
| US4031068A (en) | 1977-06-21 |
| FR2359820B1 (Direct) | 1981-11-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |