CN1878852A - 用作可聚合化合物的稳定剂的自由基捕集剂 - Google Patents
用作可聚合化合物的稳定剂的自由基捕集剂 Download PDFInfo
- Publication number
- CN1878852A CN1878852A CNA2004800330735A CN200480033073A CN1878852A CN 1878852 A CN1878852 A CN 1878852A CN A2004800330735 A CNA2004800330735 A CN A2004800330735A CN 200480033073 A CN200480033073 A CN 200480033073A CN 1878852 A CN1878852 A CN 1878852A
- Authority
- CN
- China
- Prior art keywords
- acid
- vinyl
- carbonyl
- methyl
- alkyl
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 49
- 239000002516 radical scavenger Substances 0.000 title claims description 66
- 239000003381 stabilizer Substances 0.000 title claims description 28
- 238000000034 method Methods 0.000 claims abstract description 34
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 claims abstract description 22
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000003860 storage Methods 0.000 claims abstract description 13
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims abstract description 9
- 229960003330 pentetic acid Drugs 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- FCKYPQBAHLOOJQ-UWVGGRQHSA-N 2-[[(1s,2s)-2-[bis(carboxymethyl)amino]cyclohexyl]-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)[C@H]1CCCC[C@@H]1N(CC(O)=O)CC(O)=O FCKYPQBAHLOOJQ-UWVGGRQHSA-N 0.000 claims abstract description 3
- -1 o-hydroxy-phenyl Chemical group 0.000 claims description 141
- 229910052760 oxygen Inorganic materials 0.000 claims description 63
- 239000001301 oxygen Substances 0.000 claims description 61
- 229940123457 Free radical scavenger Drugs 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 45
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 229920002554 vinyl polymer Polymers 0.000 claims description 24
- 150000002148 esters Chemical group 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000007789 gas Substances 0.000 claims description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 11
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 7
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 6
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 230000007760 free radical scavenging Effects 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
- 229910052728 basic metal Inorganic materials 0.000 claims description 5
- 150000003818 basic metals Chemical class 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 150000002923 oximes Chemical class 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 5
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- 125000005087 alkynylcarbonyl group Chemical group 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- XQTIWNLDFPPCIU-UHFFFAOYSA-N cerium(3+) Chemical compound [Ce+3] XQTIWNLDFPPCIU-UHFFFAOYSA-N 0.000 claims description 4
- VGBWDOLBWVJTRZ-UHFFFAOYSA-K cerium(3+);triacetate Chemical compound [Ce+3].CC([O-])=O.CC([O-])=O.CC([O-])=O VGBWDOLBWVJTRZ-UHFFFAOYSA-K 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000002466 imines Chemical class 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 150000004053 quinones Chemical class 0.000 claims description 4
- 150000003672 ureas Chemical class 0.000 claims description 4
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- ZGHNHKVUNFYLAY-UHFFFAOYSA-N CC=NC(=O)N(C=C)C=C Chemical compound CC=NC(=O)N(C=C)C=C ZGHNHKVUNFYLAY-UHFFFAOYSA-N 0.000 claims description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 3
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 3
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 3
- BNKAXGCRDYRABM-UHFFFAOYSA-N ethenyl dihydrogen phosphate Chemical compound OP(O)(=O)OC=C BNKAXGCRDYRABM-UHFFFAOYSA-N 0.000 claims description 3
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 3
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims description 3
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 5
- 238000006116 polymerization reaction Methods 0.000 abstract description 10
- 238000002360 preparation method Methods 0.000 abstract description 3
- 229960001484 edetic acid Drugs 0.000 abstract 2
- 230000000087 stabilizing effect Effects 0.000 abstract 1
- 239000002585 base Substances 0.000 description 74
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000178 monomer Substances 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 229960003742 phenol Drugs 0.000 description 7
- JEFSTMHERNSDBC-UHFFFAOYSA-N 1,2-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC=CCC1(C)O JEFSTMHERNSDBC-UHFFFAOYSA-N 0.000 description 6
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- BTVVNGIPFPKDHO-UHFFFAOYSA-K cerium(3+);octadecanoate Chemical compound [Ce+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O BTVVNGIPFPKDHO-UHFFFAOYSA-K 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 5
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 5
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 4
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 4
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 3
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 3
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 3
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 3
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- JVTZFYYHCGSXJV-UHFFFAOYSA-N isovanillin Chemical compound COC1=CC=C(C=O)C=C1O JVTZFYYHCGSXJV-UHFFFAOYSA-N 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical class O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical group 0.000 description 2
- PCNMALATRPXTKX-UHFFFAOYSA-N 1,4-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CCC(C)(O)C=C1 PCNMALATRPXTKX-UHFFFAOYSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical class C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 2
- AUFZRCJENRSRLY-UHFFFAOYSA-N 2,3,5-trimethylhydroquinone Chemical compound CC1=CC(O)=C(C)C(C)=C1O AUFZRCJENRSRLY-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- URDCARMUOSMFFI-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(2-hydroxyethyl)amino]acetic acid Chemical compound OCCN(CC(O)=O)CCN(CC(O)=O)CC(O)=O URDCARMUOSMFFI-UHFFFAOYSA-N 0.000 description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 2
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2MP Natural products CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 2
- FJDLQLIRZFKEKJ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanamide Chemical compound CC(C)(C)C1=CC(CCC(N)=O)=CC(C(C)(C)C)=C1O FJDLQLIRZFKEKJ-UHFFFAOYSA-N 0.000 description 2
- GMSNIKWWOQHZGF-UHFFFAOYSA-N 3-methyl-9H-xanthine Chemical compound O=C1NC(=O)N(C)C2=C1N=CN2 GMSNIKWWOQHZGF-UHFFFAOYSA-N 0.000 description 2
- PGSWEKYNAOWQDF-UHFFFAOYSA-N 3-methylcatechol Chemical compound CC1=CC=CC(O)=C1O PGSWEKYNAOWQDF-UHFFFAOYSA-N 0.000 description 2
- MBGGFXOXUIDRJD-UHFFFAOYSA-N 4-Butoxyphenol Chemical compound CCCCOC1=CC=C(O)C=C1 MBGGFXOXUIDRJD-UHFFFAOYSA-N 0.000 description 2
- LHGMHYDJNXEEFG-UHFFFAOYSA-N 4-[4-(dimethylamino)phenyl]iminocyclohexa-2,5-dien-1-one Chemical compound C1=CC(N(C)C)=CC=C1N=C1C=CC(=O)C=C1 LHGMHYDJNXEEFG-UHFFFAOYSA-N 0.000 description 2
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 2
- ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 description 2
- ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 2
- MEPYMUOZRROULQ-UHFFFAOYSA-N 4-tert-butyl-2,6-dimethylphenol Chemical compound CC1=CC(C(C)(C)C)=CC(C)=C1O MEPYMUOZRROULQ-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FYEHYMARPSSOBO-UHFFFAOYSA-N Aurin Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)=C1C=CC(=O)C=C1 FYEHYMARPSSOBO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 2
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 2
- PXIKRTCSSLJURC-UHFFFAOYSA-N Dihydroeugenol Chemical compound CCCC1=CC=C(O)C(OC)=C1 PXIKRTCSSLJURC-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- 240000000233 Melia azedarach Species 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 238000001069 Raman spectroscopy Methods 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000002648 azanetriyl group Chemical group *N(*)* 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N beta-Tocopherol Natural products OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- GZIFEOYASATJEH-VHFRWLAGSA-N delta-Tocopherol Natural products OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-VHFRWLAGSA-N 0.000 description 2
- LZDSILRDTDCIQT-UHFFFAOYSA-N dinitrogen trioxide Chemical compound [O-][N+](=O)N=O LZDSILRDTDCIQT-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- IRSFLDGTOHBADP-UHFFFAOYSA-N embelin Chemical compound CCCCCCCCCCCC1=C(O)C(=O)C=C(O)C1=O IRSFLDGTOHBADP-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229930182817 methionine Natural products 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- OSSQSXOTMIGBCF-UHFFFAOYSA-N non-1-yne Chemical group CCCCCCCC#C OSSQSXOTMIGBCF-UHFFFAOYSA-N 0.000 description 2
- 125000001402 nonanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 150000003053 piperidines Chemical class 0.000 description 2
- DXGIRFAFSFKYCF-UHFFFAOYSA-N propanehydrazide Chemical compound CCC(=O)NN DXGIRFAFSFKYCF-UHFFFAOYSA-N 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- KEQHJBNSCLWCAE-UHFFFAOYSA-N thymoquinone Chemical compound CC(C)C1=CC(=O)C(C)=CC1=O KEQHJBNSCLWCAE-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- DFUSDJMZWQVQSF-XLGIIRLISA-N (2r)-2-methyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol Chemical compound OC1=CC=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 DFUSDJMZWQVQSF-XLGIIRLISA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- PVPBBTJXIKFICP-UHFFFAOYSA-N (7-aminophenothiazin-3-ylidene)azanium;chloride Chemical compound [Cl-].C1=CC(=[NH2+])C=C2SC3=CC(N)=CC=C3N=C21 PVPBBTJXIKFICP-UHFFFAOYSA-N 0.000 description 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 1
- JJZONEUCDUQVGR-VCFJNTAESA-N (NE)-N-[(2Z)-2-hydroxyimino-1,2-diphenylethylidene]hydroxylamine Chemical compound O\N=C(\C(=N/O)\C1=CC=CC=C1)/C1=CC=CC=C1 JJZONEUCDUQVGR-VCFJNTAESA-N 0.000 description 1
- RSJDEVMJZLLAHS-WYMLVPIESA-N (NE)-N-[phenyl(pyridin-2-yl)methylidene]hydroxylamine Chemical compound C=1C=CC=NC=1C(=N/O)/C1=CC=CC=C1 RSJDEVMJZLLAHS-WYMLVPIESA-N 0.000 description 1
- FGYKUFVNYVMTAM-UHFFFAOYSA-N (R)-2,5,8-trimethyl-2-(4,8,12-trimethyl-trideca-3t,7t,11-trienyl)-chroman-6-ol Natural products OC1=CC(C)=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-UHFFFAOYSA-N 0.000 description 1
- VTWKXBJHBHYJBI-SOFGYWHQSA-N (ne)-n-benzylidenehydroxylamine Chemical compound O\N=C\C1=CC=CC=C1 VTWKXBJHBHYJBI-SOFGYWHQSA-N 0.000 description 1
- 125000006033 1,1-dimethyl-2-propenyl group Chemical group 0.000 description 1
- 125000006060 1,1-dimethyl-3-butenyl group Chemical group 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 125000006034 1,2-dimethyl-1-propenyl group Chemical group 0.000 description 1
- 125000006035 1,2-dimethyl-2-propenyl group Chemical group 0.000 description 1
- 125000006063 1,2-dimethyl-3-butenyl group Chemical group 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- 125000006066 1,3-dimethyl-3-butenyl group Chemical group 0.000 description 1
- XJDDLMJULQGRLU-UHFFFAOYSA-N 1,3-dioxane-4,6-dione Chemical compound O=C1CC(=O)OCO1 XJDDLMJULQGRLU-UHFFFAOYSA-N 0.000 description 1
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- TYDWLFLYOFZAJR-UHFFFAOYSA-N 1-decyl-2-ethenylbenzene Chemical compound CCCCCCCCCCC1=CC=CC=C1C=C TYDWLFLYOFZAJR-UHFFFAOYSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical group CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- MMFCEMSIUPCRLD-UHFFFAOYSA-N 1-ethenyl-4-methylimidazole Chemical compound CC1=CN(C=C)C=N1 MMFCEMSIUPCRLD-UHFFFAOYSA-N 0.000 description 1
- PBGPBHYPCGDFEZ-UHFFFAOYSA-N 1-ethenylpiperidin-2-one Chemical compound C=CN1CCCCC1=O PBGPBHYPCGDFEZ-UHFFFAOYSA-N 0.000 description 1
- 125000006080 1-ethyl-1-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000006036 1-ethyl-1-propenyl group Chemical group 0.000 description 1
- 125000006082 1-ethyl-2-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000006037 1-ethyl-2-propenyl group Chemical group 0.000 description 1
- 125000006075 1-ethyl-3-butenyl group Chemical group 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- LHBQGXZUVXFJRH-UHFFFAOYSA-N 1-hydroxybut-3-en-2-one Chemical compound OCC(=O)C=C LHBQGXZUVXFJRH-UHFFFAOYSA-N 0.000 description 1
- 125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000006030 1-methyl-3-butenyl group Chemical group 0.000 description 1
- 125000006052 1-methyl-3-pentenyl group Chemical group 0.000 description 1
- 125000006055 1-methyl-4-pentenyl group Chemical group 0.000 description 1
- 125000004806 1-methylethylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- WJGPNUBJBMCRQH-UHFFFAOYSA-N 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-ol Chemical compound C1=CC(O)=C2OC(C)(C)CC2=C1 WJGPNUBJBMCRQH-UHFFFAOYSA-N 0.000 description 1
- 125000006067 2,2-dimethyl-3-butenyl group Chemical group 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- OGVLEPMNNPZAPS-UHFFFAOYSA-N 2,3-difluoropyridine Chemical compound FC1=CC=CN=C1F OGVLEPMNNPZAPS-UHFFFAOYSA-N 0.000 description 1
- QHUHPERZCBUMRK-UHFFFAOYSA-N 2,3-dimethoxypyridine Chemical compound COC1=CC=CN=C1OC QHUHPERZCBUMRK-UHFFFAOYSA-N 0.000 description 1
- OUYLXVQKVBXUGW-UHFFFAOYSA-N 2,3-dimethyl-1h-pyrrole Chemical compound CC=1C=CNC=1C OUYLXVQKVBXUGW-UHFFFAOYSA-N 0.000 description 1
- 125000006070 2,3-dimethyl-3-butenyl group Chemical group 0.000 description 1
- OWWIWYDDISJUMY-UHFFFAOYSA-N 2,3-dimethylbut-1-ene Chemical group CC(C)C(C)=C OWWIWYDDISJUMY-UHFFFAOYSA-N 0.000 description 1
- VRMNMYMLBAVRDD-UHFFFAOYSA-N 2,3-ditert-butyl-4-methoxyphenol Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1C(C)(C)C VRMNMYMLBAVRDD-UHFFFAOYSA-N 0.000 description 1
- PDOIGRRPKSYVKH-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O.OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O PDOIGRRPKSYVKH-UHFFFAOYSA-N 0.000 description 1
- QFSYADJLNBHAKO-UHFFFAOYSA-N 2,5-dihydroxy-1,4-benzoquinone Chemical compound OC1=CC(=O)C(O)=CC1=O QFSYADJLNBHAKO-UHFFFAOYSA-N 0.000 description 1
- DDXYWFGBQZICBD-UHFFFAOYSA-N 2,6-di(propan-2-yl)cyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)C1=CC(=O)C=C(C(C)C)C1=O DDXYWFGBQZICBD-UHFFFAOYSA-N 0.000 description 1
- SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- VMZVBRIIHDRYGK-UHFFFAOYSA-N 2,6-ditert-butyl-4-[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VMZVBRIIHDRYGK-UHFFFAOYSA-N 0.000 description 1
- UOBBOIBRASNGFK-UHFFFAOYSA-N 2-(2-hydroxyphenyl)cyclohexa-2,5-diene-1,4-dione Chemical compound OC1=CC=CC=C1C1=CC(=O)C=CC1=O UOBBOIBRASNGFK-UHFFFAOYSA-N 0.000 description 1
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- IBTKQVRMPSIGNC-UHFFFAOYSA-N 2-amino-5-methylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C(N)=CC1=O IBTKQVRMPSIGNC-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- MCRZWYDXIGCFKO-UHFFFAOYSA-N 2-butylpropanedioic acid Chemical compound CCCCC(C(O)=O)C(O)=O MCRZWYDXIGCFKO-UHFFFAOYSA-N 0.000 description 1
- 125000006078 2-ethyl-3-butenyl group Chemical group 0.000 description 1
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- ZNCUUYCDKVNVJH-UHFFFAOYSA-N 2-isopropoxyphenol Chemical compound CC(C)OC1=CC=CC=C1O ZNCUUYCDKVNVJH-UHFFFAOYSA-N 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000006031 2-methyl-3-butenyl group Chemical group 0.000 description 1
- 125000006053 2-methyl-3-pentenyl group Chemical group 0.000 description 1
- 125000006056 2-methyl-4-pentenyl group Chemical group 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- NKTDTMONXHODTI-UHFFFAOYSA-N 2-pentyne Chemical compound CCC#CC NKTDTMONXHODTI-UHFFFAOYSA-N 0.000 description 1
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
- NDMARPMDNRJSNY-UHFFFAOYSA-N 2-tert-butyl-4-ethyl-5-methylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C=C1C NDMARPMDNRJSNY-UHFFFAOYSA-N 0.000 description 1
- BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical compound CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- UPVYFJALDJUSOV-UHFFFAOYSA-N 3,5-Bis(1,1-dimethylethyl)-4-hydroxy-benzoic acid ethyl ester Chemical class COC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 UPVYFJALDJUSOV-UHFFFAOYSA-N 0.000 description 1
- LKZQGRDTKAOCAV-UHFFFAOYSA-N 3-benzyl-2,5-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=CC(=O)C(C)=C1CC1=CC=CC=C1 LKZQGRDTKAOCAV-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- SXGXVOZDLWXVKM-UHFFFAOYSA-N 3-dodecylpyrrolidine-2,5-dione Chemical compound CCCCCCCCCCCCC1CC(=O)NC1=O SXGXVOZDLWXVKM-UHFFFAOYSA-N 0.000 description 1
- 125000006041 3-hexenyl group Chemical group 0.000 description 1
- UMYJQPRVRNMXKM-UHFFFAOYSA-N 3-hydroxy-2,5-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C(C)=C(O)C1=O UMYJQPRVRNMXKM-UHFFFAOYSA-N 0.000 description 1
- QXIQCNFSNJEMOD-UHFFFAOYSA-N 3-hydroxybutan-2-yl prop-2-enoate Chemical compound CC(O)C(C)OC(=O)C=C QXIQCNFSNJEMOD-UHFFFAOYSA-N 0.000 description 1
- NDACNGSDAFKTGE-UHFFFAOYSA-N 3-hydroxydiphenylamine Chemical compound OC1=CC=CC(NC=2C=CC=CC=2)=C1 NDACNGSDAFKTGE-UHFFFAOYSA-N 0.000 description 1
- 125000006032 3-methyl-3-butenyl group Chemical group 0.000 description 1
- 125000006054 3-methyl-3-pentenyl group Chemical group 0.000 description 1
- 125000006057 3-methyl-4-pentenyl group Chemical group 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- FKIOYBLZUCCLTL-UHFFFAOYSA-N 4-butyl-2-tert-butyl-5-methylphenol Chemical compound CCCCC1=CC(C(C)(C)C)=C(O)C=C1C FKIOYBLZUCCLTL-UHFFFAOYSA-N 0.000 description 1
- HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical compound OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 description 1
- 125000006042 4-hexenyl group Chemical group 0.000 description 1
- JTTMYKSFKOOQLP-UHFFFAOYSA-N 4-hydroxydiphenylamine Chemical compound C1=CC(O)=CC=C1NC1=CC=CC=C1 JTTMYKSFKOOQLP-UHFFFAOYSA-N 0.000 description 1
- ILKNNHYSEPMBSD-UHFFFAOYSA-N 4-methoxyphenol Chemical compound COC1=CC=C(O)C=C1.COC1=CC=C(O)C=C1 ILKNNHYSEPMBSD-UHFFFAOYSA-N 0.000 description 1
- 125000003119 4-methyl-3-pentenyl group Chemical group [H]\C(=C(/C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006058 4-methyl-4-pentenyl group Chemical group 0.000 description 1
- SLMFWJQZLPEDDU-UHFFFAOYSA-N 4-methylpent-2-yne Chemical compound CC#CC(C)C SLMFWJQZLPEDDU-UHFFFAOYSA-N 0.000 description 1
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical group C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 description 1
- ALJHHTHBYJROOG-UHFFFAOYSA-N 7-(dimethylamino)phenothiazin-3-one Chemical compound C1=CC(=O)C=C2SC3=CC(N(C)C)=CC=C3N=C21 ALJHHTHBYJROOG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- MJBPUQUGJNAPAZ-UHFFFAOYSA-N Butine Natural products O1C2=CC(O)=CC=C2C(=O)CC1C1=CC=C(O)C(O)=C1 MJBPUQUGJNAPAZ-UHFFFAOYSA-N 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- 125000005865 C2-C10alkynyl group Chemical group 0.000 description 1
- 241001060848 Carapidae Species 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 150000000703 Cerium Chemical class 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- GZIFEOYASATJEH-UHFFFAOYSA-N D-delta tocopherol Natural products OC1=CC(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- 229920001174 Diethylhydroxylamine Polymers 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 1
- UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Natural products COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 description 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- 241000264060 Lethrinus Species 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical class C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- XUYPXLNMDZIRQH-LURJTMIESA-N N-acetyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-LURJTMIESA-N 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Natural products OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- 241000775848 Syringa oblata Species 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- 239000006035 Tryptophane Substances 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- RYQWRHUSMUEYST-UHFFFAOYSA-N [14]annulene Chemical compound C1=CC=CC=CC=CC=CC=CC=C1 RYQWRHUSMUEYST-UHFFFAOYSA-N 0.000 description 1
- ZRXMAKJQOXJHQF-UHFFFAOYSA-N [2-(2-hydroxyphenyl)phenyl]-phenylmethanone Chemical compound OC1=CC=CC=C1C1=CC=CC=C1C(=O)C1=CC=CC=C1 ZRXMAKJQOXJHQF-UHFFFAOYSA-N 0.000 description 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- DFYRUELUNQRZTB-UHFFFAOYSA-N apocynin Chemical compound COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 229960005261 aspartic acid Drugs 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 150000001538 azepines Chemical class 0.000 description 1
- 150000004054 benzoquinones Chemical class 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 229960003328 benzoyl peroxide Drugs 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- NKKMVIVFRUYPLQ-UHFFFAOYSA-N but-2-enenitrile Chemical compound CC=CC#N NKKMVIVFRUYPLQ-UHFFFAOYSA-N 0.000 description 1
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 1
- XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical compound C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- KSBOQWWDFBYHGC-UHFFFAOYSA-N butylbenzene ethene Chemical compound C=C.C(CCC)C1=CC=CC=C1 KSBOQWWDFBYHGC-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- GHLITDDQOMIBFS-UHFFFAOYSA-H cerium(3+);tricarbonate Chemical compound [Ce+3].[Ce+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O GHLITDDQOMIBFS-UHFFFAOYSA-H 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 1
- MTFJSAGADRTKCI-VMPITWQZSA-N chembl77510 Chemical compound O\N=C\C1=CC=CC=N1 MTFJSAGADRTKCI-VMPITWQZSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- XHFVDZNDZCNTLT-UHFFFAOYSA-H chromium(3+);tricarbonate Chemical compound [Cr+3].[Cr+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O XHFVDZNDZCNTLT-UHFFFAOYSA-H 0.000 description 1
- BJIOGJUNALELMI-ARJAWSKDSA-N cis-isoeugenol Chemical compound COC1=CC(\C=C/C)=CC=C1O BJIOGJUNALELMI-ARJAWSKDSA-N 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- WASNBVDBYSQBPH-UHFFFAOYSA-N coerulignone Chemical compound C1=C(OC)C(=O)C(OC)=CC1=C1C=C(OC)C(=O)C(OC)=C1 WASNBVDBYSQBPH-UHFFFAOYSA-N 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 1
- DCZFGQYXRKMVFG-UHFFFAOYSA-N cyclohexane-1,4-dione Chemical compound O=C1CCC(=O)CC1 DCZFGQYXRKMVFG-UHFFFAOYSA-N 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical class C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005070 decynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical group CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 1
- HBEDSQVIWPRPAY-UHFFFAOYSA-N dihydro-benzofuran Natural products C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- JGUQDUKBUKFFRO-CIIODKQPSA-N dimethylglyoxime Chemical compound O/N=C(/C)\C(\C)=N\O JGUQDUKBUKFFRO-CIIODKQPSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- OMBRFUXPXNIUCZ-UHFFFAOYSA-N dioxidonitrogen(1+) Chemical compound O=[N+]=O OMBRFUXPXNIUCZ-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical group C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- WAMKWBHYPYBEJY-UHFFFAOYSA-N duroquinone Chemical compound CC1=C(C)C(=O)C(C)=C(C)C1=O WAMKWBHYPYBEJY-UHFFFAOYSA-N 0.000 description 1
- FGYKUFVNYVMTAM-MUUNZHRXSA-N epsilon-Tocopherol Natural products OC1=CC(C)=C2O[C@@](CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-MUUNZHRXSA-N 0.000 description 1
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 1
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 1
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- TUBUGIPAUYMXPQ-UHFFFAOYSA-N formaldehyde;2-methoxyphenol Chemical compound O=C.COC1=CC=CC=C1O TUBUGIPAUYMXPQ-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 229960002743 glutamine Drugs 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- YVXHZKKCZYLQOP-UHFFFAOYSA-N hept-1-yne Chemical compound CCCCCC#C YVXHZKKCZYLQOP-UHFFFAOYSA-N 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YJSSCAJSFIGKSN-UHFFFAOYSA-N hex-1-en-2-ylbenzene Chemical compound CCCCC(=C)C1=CC=CC=C1 YJSSCAJSFIGKSN-UHFFFAOYSA-N 0.000 description 1
- MELUCTCJOARQQG-UHFFFAOYSA-N hex-2-yne Chemical compound CCCC#CC MELUCTCJOARQQG-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 229940100630 metacresol Drugs 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- CMIAIUZBKPLIOP-YZLZLFLDSA-N methyl (1r,4ar,4br,10ar)-7-(2-hydroperoxypropan-2-yl)-4a-methyl-2,3,4,4b,5,6,10,10a-octahydro-1h-phenanthrene-1-carboxylate Chemical compound C1=C(C(C)(C)OO)CC[C@@H]2[C@]3(C)CCC[C@@H](C(=O)OC)[C@H]3CC=C21 CMIAIUZBKPLIOP-YZLZLFLDSA-N 0.000 description 1
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical group COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- GWLOGZRVYXAHRE-UHFFFAOYSA-N n,4-dimethylbenzenesulfonamide Chemical group CNS(=O)(=O)C1=CC=C(C)C=C1 GWLOGZRVYXAHRE-UHFFFAOYSA-N 0.000 description 1
- UCMYJOPIPDLTRT-UHFFFAOYSA-N n,n-diethyl-2-nitrosoaniline Chemical compound CCN(CC)C1=CC=CC=C1N=O UCMYJOPIPDLTRT-UHFFFAOYSA-N 0.000 description 1
- PULCKIYKBGOTTG-UHFFFAOYSA-N n-(2,4-dimethylpentan-3-ylidene)hydroxylamine Chemical compound CC(C)C(=NO)C(C)C PULCKIYKBGOTTG-UHFFFAOYSA-N 0.000 description 1
- XIOIFAFSEIOPFO-UHFFFAOYSA-N n-(4-tert-butylcyclohexylidene)hydroxylamine Chemical compound CC(C)(C)C1CCC(=NO)CC1 XIOIFAFSEIOPFO-UHFFFAOYSA-N 0.000 description 1
- 229940048195 n-(hydroxyethyl)ethylenediaminetriacetic acid Drugs 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- GORGQKRVQGXVEB-UHFFFAOYSA-N n-ethenyl-n-ethylacetamide Chemical compound CCN(C=C)C(C)=O GORGQKRVQGXVEB-UHFFFAOYSA-N 0.000 description 1
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 description 1
- OFESGEKAXKKFQT-UHFFFAOYSA-N n-ethenyl-n-methylformamide Chemical compound C=CN(C)C=O OFESGEKAXKKFQT-UHFFFAOYSA-N 0.000 description 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- HAZULKRCTMKQAS-UHFFFAOYSA-N n-ethenylbutanamide Chemical compound CCCC(=O)NC=C HAZULKRCTMKQAS-UHFFFAOYSA-N 0.000 description 1
- IUWVWLRMZQHYHL-UHFFFAOYSA-N n-ethenylpropanamide Chemical compound CCC(=O)NC=C IUWVWLRMZQHYHL-UHFFFAOYSA-N 0.000 description 1
- CRNNFEKVPRFZKJ-UHFFFAOYSA-N n-fluoren-9-ylidenehydroxylamine Chemical compound C1=CC=C2C(=NO)C3=CC=CC=C3C2=C1 CRNNFEKVPRFZKJ-UHFFFAOYSA-N 0.000 description 1
- VLVVDHDKRHWUSQ-UHFFFAOYSA-N n-heptan-4-ylidenehydroxylamine Chemical compound CCCC(=NO)CCC VLVVDHDKRHWUSQ-UHFFFAOYSA-N 0.000 description 1
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- NAQQTJZRCYNBRX-UHFFFAOYSA-N n-pentan-3-ylidenehydroxylamine Chemical compound CCC(CC)=NO NAQQTJZRCYNBRX-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KOOMFXGDLMRWSN-UHFFFAOYSA-N n-phenylnitrous amide Chemical compound O=NNC1=CC=CC=C1 KOOMFXGDLMRWSN-UHFFFAOYSA-N 0.000 description 1
- IBXNCJKFFQIKKY-UHFFFAOYSA-N n-propylacetylene Natural products CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 description 1
- NYEPSLKMENGNDO-UHFFFAOYSA-N n-tert-butyl-4-methylbenzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)NC(C)(C)C)C=C1 NYEPSLKMENGNDO-UHFFFAOYSA-N 0.000 description 1
- YUIVHZARNDKOHO-UHFFFAOYSA-N n-tert-butyl-n-methylprop-2-enamide Chemical compound CC(C)(C)N(C)C(=O)C=C YUIVHZARNDKOHO-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- RPMXALUWKZHYOV-UHFFFAOYSA-N nitroethene Chemical group [O-][N+](=O)C=C RPMXALUWKZHYOV-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical compound CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 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
- 238000010926 purge Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- ORIHZIZPTZTNCU-YVMONPNESA-N salicylaldoxime Chemical compound O\N=C/C1=CC=CC=C1O ORIHZIZPTZTNCU-YVMONPNESA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
- 238000010555 transalkylation reaction Methods 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- OOZBTDPWFHJVEK-UHFFFAOYSA-N tris(2-nonylphenyl) phosphate Chemical compound CCCCCCCCCC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC OOZBTDPWFHJVEK-UHFFFAOYSA-N 0.000 description 1
- 229960004799 tryptophan Drugs 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- FGYKUFVNYVMTAM-WAZJVIJMSA-N β-tocotrienol Chemical compound OC1=CC(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-WAZJVIJMSA-N 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
- C07B63/04—Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
-
- 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
- C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
Abstract
一种用于在制备、储存和/或运输过程中稳定可聚合化合物使之不发生聚合的方法,其中使用至少一种含有至少两个甘氨酸单元的自由基捕集剂,前提条件为该自由基捕集剂不选自乙二胺四乙酸(EDTA)、二亚乙基三胺五乙酸(DTPA)、反式1,2-环己二胺四乙酸(CYDTA)及其碱金属与碱土金属盐。
Description
本发明描述了自由基清除剂在稳定可聚合化合物使之不发生聚合中的用途。
已知的是,例如通过加热、光或过氧化物的作用可以容易引起可聚合化合物聚合。然而,因为生产、后处理、储存和/或运输过程中的安全和经济原因必须减弱或减少聚合,因此对新型、有效的阻聚剂一直存在需求。
特别有问题的是在后处理如通过蒸馏或精馏,以及随后的储存和运输过程中的化学和/或物理加工。
用于可聚合化合物的大量稳定剂是已知的,特别是用于丙烯酸和甲基丙烯酸(下面称为(甲基)丙烯酸)及其酯(下面称为(甲基)丙烯酸酯)的那些。
GB-A 1 601 979描述了在EDTA作为螯合剂存在下用亚硝基苯酚酯稳定(甲基)丙烯酸盐水溶液。
US 4,929,660公开了含有自由基丙烯酸单体和阻聚剂、金属鳌合剂和自由基清除剂的粘合剂组合物。该自由基清除剂为N,N-二烷基-或N,N-二芳烷基羟胺。
在金属清除剂存在下稳定不饱和季铵盐描述于US 5,912,383中。这些金属清除剂可以为二亚乙基三胺五乙酸和N-(羟乙基)乙二胺三乙酸以及相关的钠盐。
DE-A 199 20 796描述了通过将莰烯与(甲基)丙烯酸反应而制备(甲基)丙烯酸异冰片酯的方法,该方法也在螯合形成剂存在下进行。在该出版物中,公开了将次氮基三乙酸、乙二胺四乙酸、N-(2-羟乙基)乙二胺三乙酸、1,2-亚环己基二次氮基四乙酸、二亚乙基三胺五乙酸、3,6-二氧杂亚辛基二次氮基四乙酸以及这些酸的碱金属盐作为螯合形成剂。
WO 02/26685描述了在氧存在下在与稳定剂一起蒸馏的过程中,用金属清除剂稳定丙烯酸系单体,所述金属清除剂选自乙二胺四乙酸(EDTA)、二亚乙基三胺五乙酸(DTPA)及其钠盐(Na5DTPA)和反式1,2-环己二胺五乙酸。这些金属清除剂用于络合游离铁。
JP 05-295011和JP 05-320205也描述了在EDTA、DTPA、CYDTA及其碱金属盐存在下稳定丙烯酸。
本发明的目的是提供一种在后处理、储存和/或运输过程中稳定可聚合化合物使之不发生聚合的替代方法。
我们已经发现这个目的由一种在后处理、储存和/或运输过程中稳定可聚合化合物使之不发生聚合的方法实现,其中使用至少一种含有至少两个甘氨酸单元的自由基清除剂,前提条件为该自由基清除剂不选自乙二胺四乙酸(EDTA)、二亚乙基三胺五乙酸(DTPA)、反式1,2-环己二胺四乙酸(CYDTA)及其碱金属与碱土金属盐。
在优选的实施方案中,使用至少一种含有至少两个甘氨酸单元的自由基清除剂,前提条件为该自由基清除剂不具有≥2个下述结构单元:
其中R和R’可以互相独立地为氢或金属。例如这些金属可以为碱金属如钠或钾。
在特别优选的实施方案中,使用至少一种含有至少两个甘氨酸单元和至少一个酰胺和/或酯单元的自由基清除剂。自由基清除剂优选具有两个酰胺单元。
非常特别优选使用的自由基清除剂为式(I)的那些:
具体而言:G1可以为NR3R4或OR7并且G2可以为NR5R6或OR8。
X可以为C1-C20烷基、NCH2COOR9、NR10、O、S、PR11、Se、SiOR12R13或芳基,其中所述取代基可以在任何所需位置由一个或多个杂原子和/或卤原子取代,但不超过五次,优选不超过四次,特别优选不超过三次。X优选为C1-C20烷基或NCHCOOR9,特别优选X为C1-C10烷基或NCHCOOR9。
k、l、m和n互相独立地为0-20。l和m优选为0-10,特别优选0-5,非常特别优选0-3并且尤其优选0-2。k和n优选具有相同的值,如0-10,优选0-5,非常特别优选0-3;尤其k和n值为1。
具体而言,基团R1-R8可以具有下述含义:
R1-R6可以互相独立地为氢、C1-C20烷基、C1-C20烷基羰基、C2-C20链烯基、C2-C20链烯基羰基、C2-C20炔基、C2-C20炔基羰基、C3-C15环烷基、C5-C15环烷基羰基、芳基、芳基羰基或杂环,
R7和R8可以互相独立地为C1-C20烷基、C1-C20烷基羰基、C2-C20链烯基、C2-C20链烯基羰基、C2-C20炔基、C2-C20炔基羰基、C3-C15环烷基、C5-C15环烷基羰基、芳基、芳基羰基或杂环,
其中
a)在所述脂族取代基的情况下,基团R3与R4或R5与R6也可以互相连接并且因此可以共同形成三元至八元环,优选五元至七元环并且特别优选五元环或六元环,
b)所述脂族取代基可以为直链或支链,
c)每个所述取代基可以在任何所需位置由一个或多个杂原子插入,这些杂原子的数目不超过10,优选不超过8,特别优选不超过5并且尤其不超过3,和/或
d)每个所述取代基可以在任何所需位置由烷基、烷氧基、烷氧基羰基、芳基、芳氧基、芳氧基羰基、羟基羰基、氨羰基、杂环、杂原子或卤原子取代,但不超过五次,优选不超过四次并且特别优选不超过三次,这些取代基也可以由所述基团取代不超过两次,优选不超过一次。
R9-R13如果合适的话互相独立地为氢或C1-C20烷基。
具体而言,用以表述各种基团R的通用术语具有下述含义:
C1-C20烷基:至多20个碳原子的直链或支链烃基,优选C1-C10烷基,例如甲基、乙基、丙基、异丙基、正丁基、仲丁基、叔丁基、1,1-二甲基乙基、戊基、2-甲基丁基、1,1-二甲基丙基、1,2-二甲基丙基,2,2-二甲基丙基,1-乙基丙基、己基、2-甲基戊基、3-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基、1-乙基-2-甲基丙基、庚基、辛基、2-乙基己基、2,4,4-三甲基戊基、1,1,3,3-四甲基丁基、壬基和癸基及其异构体。
C1-C20烷基羰基:经由羰基(-CO-)连接的具有1-20个碳原子的直链或支链烷基(如上所述),优选C1-C10烷基羰基,例如甲酰基、乙酰基、正丙酰基或异丙酰基、正丁酰基、异丁酰基、仲丁酰基或叔丁酰基、正戊酰基、异戊酰基、仲戊酰基或叔戊酰基、正壬酰基、异壬酰基或正癸酰基。
C2-C20链烯基:具有2-20个碳原子和在任何所需位置的双键的不饱和直链或支链烃基,优选C2-C10链烯基,例如乙烯基、1-丙烯基、2-丙烯基、1-甲基乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-1-丁烯基、2-甲基-1-丁烯基、3-甲基-1-丁烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-乙基-1-丙烯基、1-乙基-2-丙烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、2-甲基-1-戊烯基、3-甲基-1-戊烯基、4-甲基-1-戊烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、1-甲基-3-戊烯基、2-甲基-3-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、3,3-二甲基-1-丁烯基、3,3-二甲基-2-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基、1-乙基-2-甲基-1-丙烯基和1-乙基-2-甲基-2-丙烯基以及庚烯基、辛烯基、壬烯基和癸烯基的异构体。
C2-C20链烯基羰基:经由羰基(-CO-)连接的具有2-20个碳原子和在任何所需位置的双键的不饱和直链或支链烃基(如上所述),优选C2-C10链烯基羰基,例如乙烯酰基、丙烯酰基、丁烯酰基、戊烯酰基、壬烯酰基及其异构体。
C2-C20炔基:具有2-20个碳原子和在任何所需位置的叁键的直链或支链烃基,优选C2-C10炔基,例如乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、1-戊炔基、2-戊炔基、3-戊炔基、4-戊炔基、1-甲基-2-丁炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、3-甲基-1-丁炔基、1,1-二甲基-2-丙炔基、1-乙基-2-丙炔基、1-己炔基、2-己炔基、3-己炔基、4-己炔基、5-己炔基、1-甲基-2-戊炔基、1-甲基-3-戊炔基、1-甲基-4-戊炔基、2-甲基-3-戊炔基、2-甲基-4-戊炔基、3-甲基-1-戊炔基、3-甲基-4-戊炔基、4-甲基-1-戊炔基、4-甲基-2-戊炔基、1,1-二甲基-2-丁炔基、1,1-二甲基-3-丁炔基、1,2-二甲基-3-丁炔基、2,2-二甲基-3-丁炔基、3,3-二甲基-1-丁炔基、1-乙基-2-丁炔基、1-乙基-3-丁炔基、2-乙基-3-丁炔基、1-乙基-1-甲基-2-丙炔基,以及庚炔基、辛炔基、壬炔基和癸炔基的异构体。
C2-C20炔基羰基:经由羰基(-CO-)连接的具有2-20个碳原子和在任何所需位置的叁键的不饱和直链或支链烃基(如上所述),优选C2-C10炔基羰基,例如丙炔酰基、丁炔酰基、戊炔酰基、壬炔酰基、癸炔酰基及其异构体。
C3-C15环烷基:具有3-15个碳环成员的单环饱和烃基,优选C3-C8环烷基,例如环丙基、环丁基、环戊基、环己基、环庚基和环辛基以及饱和或不饱和的环体系如降冰片基或降冰片烯基。
C3-C15环烷基羰基:经由羰基(-CO-)连接的具有3-14个碳环成员的单环饱和烃基(如上所述),优选为C3-C8环烷基羰基。
芳基:包含6-14个碳环成员的单环至三环芳环体系,例如苯基、萘基和蒽基,优选单环或双环芳环体系,特别优选单环芳环体系。
芳基羰基:经由羰基(-CO-)连接到骨架上的优选单环至三环芳环体系(如上所述),例如苯甲酰基,优选单环或双环芳环体系,特别优选单环芳环体系。
杂环:具有、合适的话具有多个含有氧原子、氮原子和/或硫原子的五元至十二元环、优选五元至九元环、特别优选五元至六元环的环体系,例如呋喃基、噻吩基、吡咯基、吡啶基、吲哚基、苯并唑基、间二氧杂环戊烯基、Dioxyl、苯并咪唑基、苯并噻唑基、二甲基吡啶基、甲基喹啉基、二甲基吡咯基、甲氧基呋喃基、二甲氧基吡啶基、二氟吡啶基、甲基噻吩基、异丙基噻吩基或叔丁基噻吩基。
每个所述取代基具体可以如上所述在任何所需位置由一个或多个杂原子插入,这些杂原子的数目不超过10个,优选不超过8个,非常特别优选不超过5个并且尤其不超过3个,和/或每个所述取代基可以在任何所需位置由烷基、烷氧基、烷氧基羰基、芳基、芳氧基、芳氧基羰基、羟基羰基、氨羰基、杂环、杂原子或卤原子取代,但不超过五次,优选不超过四次并且特别优选不超过三次,这些取代基也可以由所述基团取代不超过两次,优选不超过一次。
这里提及的化合物、烷基、芳基和杂环具有上述含义。
杂原子为氧、氮、硫或磷。
烷氧基为经由氧原子(-O-)连接到骨架上的具有1-20个碳原子的直链或支链烷基(如上所述),优选C1-C10烷氧基、例如甲氧基、乙氧基或丙氧基。
烷氧基羰基为经由羰基(-CO-)连接到骨架上的具有1-20个碳原子的烷氧基(如上所述),优选C1-C10烷氧基羰基。
芳氧基为经由氧原子(-O-)连接到骨架上的单环至三环芳环体系(如上所述),优选单环或双环芳环体系,特别优选单环芳环体系。
芳氧基羰基为经由羰基(-CO-)连接到骨架上的单环至三环芳氧基(如上所述),优选单环或双环芳氧基羰基,特别优选单环芳氧基羰基。
卤原子为氟、氯、溴和碘。
基团R1和R2优选相同并且为氢或C1-C20烷基,特别优选氢或C1-C10烷基,非常特别优选氢或C1-C6烷基。
基团R3和R5优选相同并且为氢、C1-C20烷基或C1-C20烷基羰基,特别优选氢、C1-C10烷基或C1-C10烷基羰基,非常特别优选氢、C1-C6烷基或C1-C6烷基羰基。
基团R4与R6或R7与R8优选相同并且为C1-C20烷基、C1-C20烷基羰基、芳基、C2-C20链烯基、C2-C20链烯基羰基、C2-C20炔基或C2-C20炔基羰基。如上所述,每个所述基团可以在任何所需位置由一个或多个杂原子插入,这些杂原子的数目不超过10个,优选不超过8个,非常特别优选不超过5个并且尤其不超过3个,和/或所述基团可以在任何所需位置由烷基、烷氧基、烷氧基羰基、芳基、芳氧基、芳氧基羰基、羟基羰基、氨羰基、杂环、杂原子或卤原子取代,但不超过五次,优选不超过四次并且特别优选不超过三次,这些取代基也可以由所述基团取代不超过两次,优选不超过一次。
特别优选基团R4与R6或R7与R8选自苯基、苄基、对甲氧苯基、邻羟基苯基、间羟基苯基、对羟基苯基、1-羟己基、甲基、乙基、丙基、丁基、乙二醇、二甘醇、三甘醇、具有4-10个EO单元的乙氧基化物、乙二胺、二亚乙基三胺、三亚乙基四胺和氨基酸如丙氨酸、缬氨酸、亮氨酸、异亮氨酸、脯氨酸、色氨酸、苯丙氨酸、甲硫氨酸、甘氨酸、丝氨酸、酪氨酸、苏氨酸、半胱氨酸、天冬酰胺、谷氨酰胺、天冬氨酸、谷氨酸、赖氨酸、精氨酸或组氨酸。
例如,R4与R6或R7与R8可以为表1中所提及的基团。
表1
当然,所述取代基R和X与k、l、m和n的所述数值的所有组合都是可以的。
表2汇集了优选的式(I)的各个化合物。
表2
这些化合物的制备例如以类似于描述于DE-A 101 05 014和CH-A 569405中的合成路线进行。在所述文献中公开的所述化合物在金属缺乏现象中用作金属配合物或在诊断中用作对比剂。在Bioorganic MedicinalChemistry Letters(生物有机药化学快报)11(2001),2573中公开了通用的合成路线。
通常而言,自由基清除剂单独使用或以混合物使用,使用优选不超过五种、特别优选不超过四种并且非常特别优选不超过三种上述自由基清除剂。
为了对可聚合化合物具有稳定效果的本发明自由基清除剂的使用量在本领域常规实验中确定。
例如,基于可聚合化合物,使用0.1-1000ppm,优选1-900ppm,特别优选10-800ppm,非常特别优选50-700ppm并且尤其100-500ppm的本发明自由基清除剂或自由基清除剂混合物。
根据本发明,自由基清除剂可以有利地与至少一种已知为稳定剂和/或共稳定剂的其它化合物一起使用。这些化合物描述于例如申请号为10249 507.6的在先德国专利申请中和DE-A 102 58 329、DE-A 198 56 565和EP-A 765 856中。
适合的共稳定剂为含氧气体、酚类化合物、醌类和氢醌类化合物、N-氧基化合物、芳族胺和苯二胺、亚胺、磺酰胺、肟、羟胺、脲衍生物、含磷化合物、含硫化合物、基于四氮杂轮烯(TAA)的配合剂和/或金属盐,如果适合的话以及它们的混合物。
含氧气体可以例如为具有的氧含量为0.1-100体积%、优选0.5-50体积%,特别优选1-25体积%的那些气体。例如,这些气体可以为一氧化氮、二氧化氮、氧气、三氧化二氮或空气。这些气体可以单独使用,可以以相互之间任何需要的混合物使用或与其它气体,例如与氮气、惰性气体、蒸汽、一氧化碳、二氧化碳或低级烷烃混合使用,优选为空气或空气/氮气混合物。
酚类化合物例如为苯酚、烷基苯酚,例如邻-、间-、对甲酚(甲基苯酚),2-叔丁基-4-甲基苯酚、6-叔丁基-2,4-二甲基苯酚、2,6-二叔丁基-4-甲基苯酚、2-叔丁基苯酚、4-叔丁基苯酚、2,4-二叔丁基苯酚、2-甲基-4-叔丁基苯酚、4-叔丁基-2,6-二甲基苯酚或2,2′-亚甲基二(6-叔丁基-4-甲基苯酚)、4,4′-氧联苯、3,4-亚甲基二氧二酚(芝麻酚)、3,4-二甲基苯酚、邻苯二酚(1,2-二羟基苯)、2-(1′-甲基环己-1′-基)-4,6-二甲基苯酚、2-或4-(1′-苯基乙-1′-基)苯酚、2-叔丁基-6-甲基苯酚、2,4,6-三叔丁基苯酚、2,6-二叔丁基苯酚、壬基苯酚(CAS No.11066-49-2)、辛基苯酚(CAS No.140-66-9)、2,6-二甲基苯酚、双酚A、双酚B、双酚C、双酚F、双酚S、3,3′,5,5′-四溴双酚A、2,6-二叔丁基-对甲酚,来自BASF Aktiengesellschaft的Koresin、3,5-二叔丁基-4-羟基苯甲酸甲酯、4-叔丁基邻苯二酚、2-羟基苄醇、2-甲氧基-4-甲基苯酚、2,3,6-三甲基苯酚、2,4,5-三甲基苯酚、2,4,6-三甲基苯酚、2-异丙基苯酚、4-异丙基苯酚、6-异丙基-间甲酚、β-(3,5-二叔丁基-4-羟基苯基)丙酸正十八烷酯、1,1,3-三(2-甲基-4-羟基-5-叔丁基苯基)丁烷、1,3,5-三甲基-2,4,6-三(3,5-二叔丁基-4-羟基苄基)苯、1,3,5-三(3,5-二叔丁基-4-羟基苄基)异氰脲酸酯、1,3,5-三(3,5-二叔丁基-4-羟基苯基)丙酰氧基乙基异氰脲酸酯、1,3,5-三(2,6-二甲基-3-羟基-4-叔丁基苄基)异氰脲酸酯或季戊四醇四(β-(3,5-二叔丁基-4-羟基苯基)丙酸酯)、2,6-二叔丁基-4-二甲基氨基甲基苯酚、6-仲丁基-2,4-二硝基苯酚,来自Ciba Spezialittenchemie的Irganox565、1010、1076、1141、1192、1222和1425,3-(3′,5′-二叔丁基-4′-羟基苯基)丙酸十八烷酯、3-(3′,5′-二叔丁基-4′-羟基苯基)丙酸十六烷酯、3-(3′,5′-二叔丁基-4′-羟基苯基)丙酸辛酯、3-硫杂-1,5-戊二醇二((3′,5′-二叔丁基-4′-羟基苯基)丙酸酯)、4,8-二氧杂-1,11-十一烷二醇二((3′,5′-二叔丁基-4′-羟基苯基)丙酸酯)、4,8-二氧杂-1,11-十一烷二醇二((3′-叔丁基-4′-羟基-5′-甲基苯基)丙酸酯)、1,9-壬二醇二((3′,5′-二叔丁基-4′-羟基苯基)丙酸酯)、1,7-庚二胺二(3-(3′,5′-二叔丁基-4′-羟基苯基)丙酰胺)、1,1-甲二胺二(3-(3′,5′-二叔丁基-4′-羟基苯基)丙酰胺)、3-(3′,5′-二叔丁基-4′-羟基苯基)丙酰肼、3-(3′,5′-二甲基-4′-羟基苯基)丙酰肼、二(3-叔丁基-5-乙基-2-羟基苯-1-基)甲烷、二(3,5-二叔丁基-4-羟基苯-1-基)甲烷、二(3-(1′-甲基环己-1′-基)-5-甲基-2-羟基苯-1-基)甲烷、二(3-叔丁基-2-羟基-5-甲基苯-1-基)甲烷、1,1-二(5-叔丁基-4-羟基-2-甲基苯-1-基)乙烷、二(5-叔丁基-4-羟基-2-甲基苯-1-基)硫醚、二(3-叔丁基-2-羟基-5-甲基苯-1-基)硫醚、1,1-二(3,4-二甲基-2-羟基苯-1-基)-2-甲基丙烷、1,1-二(5-叔丁基-3-甲基-2-羟基苯-1-基)丁烷、1,3,5-三(1′-(3″,5″-二叔丁基-4″-羟基苯-1″-基)甲-1′-基)-2,4,6-三甲基苯、1,1,4-三(5′-叔丁基-4′-羟基-2′-甲基苯-1′-基)丁烷和叔丁基邻苯二酚以及氨基苯酚如对氨基苯酚,亚硝基苯酚如对亚硝基苯酚、对亚硝基邻甲酚,烷氧基苯酚如甲氧基苯酚(愈创木酚(Guajacol)、邻苯二酚单甲基醚)、2-乙氧基苯酚、2-异丙氧基苯酚、4-甲氧基苯酚(氢醌单甲基醚)、单-或二叔丁基-4-甲氧基苯酚、3,5-二叔丁基-4-羟基苯甲醚、3-羟基-4-甲氧基苯甲醇、2,5-二甲氧基-4-羟基苯甲醇(紫丁香醇)、4-羟基-3-甲氧基苯甲醛(香草醛)、4-羟基-3-乙氧基苯甲醛(乙基香兰素)、3-羟基-4-甲氧基苯甲醛(异香草醛)、1-(4-羟基-3-甲氧基苯基)乙酮(乙酰香草酮)、丁子香酚、二氢丁子香酚、异丁子香酚、生育酚(如α-、β-、γ-、δ-和ε-生育酚)、母育酚、α-生育酚氢醌和2,3-二氢-2,2-二甲基-7-羟基苯并呋喃(2,2-二甲基-7-羟基香豆冉)。
适合的醌类和氢醌类化合物例如为氢醌或氢醌单甲基醚(4-甲氧基苯酚)、甲基氢醌、2,5-二叔丁基氢醌、2-甲基-对氢醌、2,3-二甲基氢醌、三甲基氢醌、4-甲基邻苯二酚、叔丁基氢醌、3-甲基邻苯二酚、苯醌、2-甲基-对氢醌、2,3-二甲基氢醌、三甲基氢醌、叔丁基氢醌、4-乙氧基苯酚、4-丁氧基苯酚、氢醌单苄基醚、对苯氧基苯酚、2-甲基氢醌、四甲基-对苯醌、1,4-环己二酮2,5-二甲酸二乙基酯、苯基-对苯醌、2,5-二甲基-3-苄基-对苯醌、2-异丙基-5-甲基-对苯醌(百里醌)、2,6-二异丙基-对苯醌、2,5-二甲基-3-羟基-对苯醌、2,5-二羟基-对苯醌、信筒子醌(embelin)、四羟基-对苯醌、2,5-二甲氧基-1,4-苯醌、2-氨基-5-甲基-对苯醌、2,5-二苯基氨基-1,4-苯醌、5,8-二羟基-1,4-萘醌、2-苯胺基-1,4-萘醌、蒽醌、N,N-二甲基靛苯胺、N,N-二苯基-对苯醌二亚胺、1,4-苯醌二肟、Coerulignon、3,3′-二叔丁基-5,5′-二甲基二苯酚合苯醌、对玫红酸(金精)、2,6-二叔丁基-4-亚苄基苯醌和2,5-二叔戊基氢醌。
适合的N-氧基(硝酰基或N-氧基自由基,具有至少一个>N-O·基团的化合物)例如为4-羟基-2,2,6,6-四甲基哌啶-N-氧基、4-氧代-2,2,6,6-四甲基哌啶-N-氧基、4-甲氧基-2,2,6,6-四甲基哌啶-N-氧基、4-乙酰氧基-2,2,6,6-四甲基哌啶-N-氧基、2,2,6,6-四甲基哌啶-N-氧基、来自BASF Aktiengesellschaft的Uvinul4040P、4,4′,4″-三(2,2,6,6-四甲基哌啶-N-氧基)亚磷酸酯、3-氧代-2,2,5,5-四甲基吡咯烷-N-氧基、1-氧基-2,2,6,6-四甲基-4-甲氧基哌啶、1-氧基-2,2,6,6-四甲基-4-三甲基甲硅烷氧基哌啶、2-乙基己酸1-氧基-2,2,6,6-四甲基哌啶-4-基酯、癸二酸1-氧基-2,2,6,6-四甲基哌啶-4-基酯、硬酯酸1-氧基-2,2,6,6-四甲基哌啶-4-基酯、苯甲酸1-氧基-2,2,6,6-四甲基哌啶-4-基酯、(4-叔丁基)苯甲酸1-氧基-2,2,6,6-四甲基哌啶-4-基酯、琥珀酸二(1-氧基-2,2,6,6-四甲基哌啶-4-基)酯、己二酸二(1-氧基-2,2,6,6-四甲基哌啶-4-基)酯、1,10-癸二酸二(1-氧基-2,2,6,6-四甲基哌啶-4-基)酯、正丁基丙二酸二(1-氧基-2,2,6,6-四甲基哌啶-4-基)酯、邻苯二甲酸二(1-氧基-2,2,6,6-四甲基哌啶-4-基)酯、间苯二甲酸二(1-氧基-2,2,6,6-四甲基哌啶-4-基)酯、对苯二甲酸二(1-氧基-2,2,6,6-四甲基哌啶-4-基)酯、六氢化对苯二甲酸二(1-氧基-2,2,6,6-四甲基哌啶-4-基)酯、N,N′-二(1-氧基-2,2,6,6-四甲基哌啶-4-基)己二酰二胺、N-(1-氧基-2,2,6,6-四甲基哌啶-4-基)己内酰胺、N-(1-氧基-2,2,6,6-四甲基哌啶-4-基)十二烷基琥珀酰亚胺、2,4,6-三(N-丁基-N-(1-氧基-2,2,6,6-四甲基哌啶-4-基))三嗪、N,N′-二(1-氧基-2,2,6,6-四甲基哌啶-4-基)-N,N′-二甲酰基-1,6-二氨基己烷和4,4′-亚乙基二(1-氧基-2,2,6,6-四甲基哌嗪-3-酮)。
适合的芳族胺或苯二胺例如为N,N-二苯胺、N-亚硝基苯胺、亚硝基二乙基苯胺、对苯二胺、N,N′-二烷基-对苯二胺。烷基可以相同或不同并且在每种情况下可以相互独立地包含1-4个碳原子并可为直链或支链,例如N,N′-二异丁基-对苯二胺、N,N′-二异丙基-对苯二胺、来自CibaSpezialittenchemie的Irganox5057、N-苯基-对苯二胺、N,N′-二苯基-对苯二胺、N-异丙基-N-苯基-对苯二胺、N,N′-二仲丁基-对苯二胺(KerobitBPD,来自BASF Aktiengesellschaft)、N-苯基-N′-异丙基-对苯二胺(Vulkanox4010,来自Bayer AG)、N-(1,3-二甲基丁基)-N′-苯基-对苯二胺、N-苯基-2-萘胺、亚氨基联苄、N,N′-二苯基联苯胺、N-苯基四苯胺、吖啶酮、3-羟基二苯胺和4-羟基二苯胺。
亚胺例如为甲基乙基亚胺、(2-羟基苯基)苯醌亚胺、(2-羟基苯基)二苯甲酮亚胺、N,N-二甲基靛苯胺、硫堇(7-氨基-3-亚氨基-3H-吩噻嗪)和亚甲紫(7-二甲基氨基-3-吩噻嗪酮)。
作为稳定剂有效的磺酰胺例如为N-甲基-4-甲苯磺酰胺、N-叔丁基-4-甲苯磺酰胺、N-叔丁基-N-氧基-4-甲苯磺酰胺、N,N′-二(4-磺胺)哌啶、3-((5-(4-氨基苯甲酰基)-2,4-二甲基苯磺酰基)乙基氨基)-4-甲基苯磺酸,如DE-A 102 58 329中所述。
肟可以例如为醛肟、酮肟或胺肟,例如在DE-A 101 39 767中所述,优选为二乙基酮肟、丙酮肟、甲基乙基酮肟、环己酮肟、苯甲醛肟、苯偶酰二肟、丁二酮肟、2-吡啶醛肟、水杨醛肟、苯基-2-吡啶基酮肟、1,4-苯醌二肟、2,3-丁二酮二肟、2,3-丁二酮单肟、9-芴酮肟、4-叔丁基-环己酮肟、N-乙氧基-亚胺逐乙酸乙酯(N-Ethoxy-acetimidsureethylester)、2,4-二甲基-3-戊酮肟、环十二烷酮肟、4-庚酮肟和二2-呋喃基乙二酮二肟或其它脂族或芳族肟或其与烷基转移试剂如烷基卤化物、三氟甲磺酸酯、磺酸酯、甲苯磺酸酯、碳酸酯、硫酸酯、磷酸酯或类似物质的反应产物。
羟胺例如为N,N-二乙基羟胺和公开于申请号为PCT/EP/03/03139的国际申请案中的那些。
适合的脲衍生物例如为尿素或硫脲。
含磷化合物例如为三苯基膦、亚磷酸三苯酯、次磷酸、亚磷酸三壬酯、亚磷酸三乙酯或二苯基异丙基膦。
适合的含硫化合物例如为二苯硫醚、吩噻嗪和含硫的天然物质如半胱氨酸。
基于四氮杂轮烯(TAA)的配合剂例如为二苯并四氮杂[14]轮烯和卟啉,如在Chem.Soc.Rev.(化学会评论)27(1998),105-115中所提及。
金属盐例如为铜、锰、铈、镍和铬的碳酸盐、氯化物、二硫代氨基甲酸盐、硫酸盐、水杨酸盐、乙酸盐、硬脂酸盐或乙基己酸盐。
优选的共稳定剂为含氧气体、吩噻嗪、邻-、间-或对甲酚(甲基苯酚)、2-叔丁基-4-甲基苯酚、2,6-二叔丁基-4-甲基苯酚、2-叔丁基苯酚、4-叔丁基苯酚、2,4-二叔丁基苯酚、邻苯二酚(1,2-二羟基苯)、2,6-二叔丁基苯酚、4-叔丁基-2,6-二甲基苯酚、辛基苯酚(140-66-9)、壬基苯酚(11066-49-2)、2,6-二甲基苯酚、2,6-二叔丁基-对甲酚、双酚A、叔丁基邻苯二酚、氢醌、氢醌单甲基醚或甲基氢醌、2,2,6,6-四甲基哌啶-N-氧基、4-羟基-2,2,6,6-四甲基哌啶-N-氧基、4-氧代-2,2,6,6-四甲基哌啶-N-氧基和乙酸锰(II)、碳酸铈(III)、乙酸铈(III)或乙基己酸铈(III)、硬脂酸铈(III)及其具有不同组成的混合物。
尤其适合的是空气、空气/氮气混合物、吩噻嗪、邻-、间-或对甲酚(甲基苯酚)、2,6-二叔丁基-4-甲基苯酚、4-叔丁基苯酚、4-叔丁基-2,6-二甲基苯酚、辛基苯酚(140-66-9)、壬基苯酚(11066-49-2)、2,6-二甲基苯酚、2,6-二叔丁基-对甲酚、叔丁基邻苯二酚、氢醌、氢醌单甲基醚或甲基氢醌、2,2,6,6-四甲基哌啶-N-氧基、4-羟基-2,2,6,6-四甲基哌啶-N-氧基、4-氧代-2,2,6,6-四甲基哌啶-N-氧基和乙酸铈(III)或乙基己酸铈(III)以及至少两种所述组份的混合物。
特别优选的是空气、空气/氮气混合物、吩噻嗪、氢醌、氢醌单甲基醚、2,2,6,6-四甲基哌啶-N-氧基、4-羟基-2,2,6,6-四甲基哌啶-N-氧基、4-氧代-2,2,6,6-四甲基哌啶-N-氧基、N,N′-二仲丁基-对苯二胺、乙酸铈(III)或乙基己酸铈(III)及其混合物。
待用的本发明稳定剂和任何共稳定剂的添加方法没有限制。在任一种情况下,添加的本发明稳定剂可以单独地或与其它本发明稳定剂和/或与上述共稳定剂作为混合物以液体的形式或以在适合溶剂中的溶解形式添加,该溶剂本身可以为稳定剂,例如由DE-A 102 00 583所述。此外,适合的溶剂例如为来自制备可聚合化合物的物料流。这些可以例如为纯产物,即可聚合化合物,通常纯度为95%或更高,优选为98%或更高且尤其优选为99%或更高;而且也可为用于制备可聚合化合物的原料,纯度为95%或更高,优选为98%或更高且特别优选为99%或更高;或为含有原料和/或产物和/或中间体和/或副产物的那些物料流。
所用溶液的浓度仅受稳定剂/稳定剂混合物在溶剂中的溶解度限制;例如,其可以为0.1-50重量%,优选0.2-25重量%,尤其优选0.3-10重量%,非常特别优选0.5-5重量%。
当然,本发明自由基清除剂或自由基清除剂混合物也可以以熔化的形式使用。例如,当熔点低于120℃,优选低于100℃,尤其优选低于80℃并且尤其低于60℃时。
在更优选的实施方案中,本发明自由基清除剂或自由基清除剂混合物以熔化的形式使用,并将熔点低于120℃,优选低于100℃,特别优选低于80℃并且尤其低于60℃的酚类作为共稳定剂。所述酚特别优选选自对氨基苯酚、对亚硝基苯酚、2-叔丁基苯酚、4-叔丁基苯酚、2,4-二叔丁基苯酚、2-甲基-4-叔丁基苯酚、4-叔丁基-2,6-二甲基苯酚、氢醌和氢醌单甲基醚。
如上所述,基于可聚合化合物,使用0.1-1000ppm的本发明自由基清除剂或自由基清除剂混合物。如果本发明自由基清除剂混合物与共稳定剂一起使用,其基于可聚合化合物的用量为0.1-5000ppm,优选1-4000ppm,特别优选5-2500ppm、尤其优选10-1000ppm并且尤其50-750ppm。
如果使用多种稳定剂或共稳定剂的混合物,这些都可以互相独立地溶解于不同溶剂中在不同计量点或在同一计量点互相独立地供入。
根据本发明,如果可聚合化合物暴露于聚合风险中,如由于高纯度、长储存时间和/或高温,稳定剂/稳定剂混合物优选在可聚合化合物的这些点上使用。
这些例如可以为吸收单元、解吸单元、精馏单元如蒸馏装置或精馏塔、蒸发器如自然循环或强迫循环蒸发器、冷凝器或真空单元。
例如,稳定剂可以在精馏单元的顶部计量加入,例如喷射或喷雾进入精馏单元的顶部或进入取出内部构件或经由具有分离作用的内部构件如塔板、填充物、隔板或床,或与回流一起如用喷射计量加入冷凝器使得冷凝器的顶部和/或冷却表面湿润,或如EP-A 1 057 804所述进入真空单元或如DE-A 101 43 565所述作为密封液体进入液体环式泵。
根据本发明使用的自由基清除剂可用作储存稳定剂和运输稳定剂,即用来稳定纯净的可聚合化合物。
此外,本发明涉及稳定剂混合物,其包含:
i)至少一种含有至少两个甘氨酸单元的自由基清除剂,前提条件为该自由基清除剂不选自乙二胺四乙酸(EDTA)、二亚乙基三胺五乙酸(DTPA)、反式1,2-环己二胺四乙酸(CYDTA)及其碱金属与碱土金属盐,和
ii)至少一种其它稳定剂或共稳定剂。
其中,具有至少两个甘氨酸单元的自由基清除剂i)为优选含有至少一个酰胺和/或酯单元的化合物,尤其优选式(I)的自由基清除剂。当然,本发明也涉及包含上述优选的本发明自由基清除剂的稳定剂混合物。
所有上述组份的组合也是可行的。
稳定剂或共稳定剂为上述含氧气体、酚类化合物、醌类和氢醌类化合物、N-氧基化合物、芳族胺和苯二胺、亚胺、磺酰胺、肟、羟胺、脲衍生物、含磷化合物和/或含硫化合物、基于TAA的配合剂和/或金属盐。
优选稳定剂混合物包含自由基清除剂和吩噻嗪、自由基清除剂/氢醌、自由基清除剂/氢醌单甲基醚、自由基清除剂/4-羟基-2,2,6,6-四甲基哌啶-N-氧基、自由基清除剂/4-氧代-2,2,6,6-四甲基哌啶-N-氧基、自由基清除剂/2,2,6,6-四甲基哌啶-N-氧基、自由基清除剂/吩噻嗪/氢醌单甲基醚、自由基清除剂/吩噻嗪/4-羟基-2,2,6,6-四甲基哌啶-N-氧基或自由基清除剂/氢醌单甲基醚/4-羟基-2,2,6,6-四甲基哌啶-N-氧基,以及如果合适的话在每种情况下还包含至少一种所述铈盐,在每种情况下存在或不存在含氧气体,优选存在含氧气体。
本发明稳定剂混合物含有组份i)和ii)并且重量比率i)∶ii)为1∶100-100∶1,优选1∶50-50∶1,特别优选1∶10-10∶1并且尤其1∶5-5∶1。
此外,本发明涉及含有上述本发明稳定剂混合物和至少一种可聚合化合物的混合物。可以为本发明稳定剂混合物与可聚合化合物的所有组合。
本发明也涉及含有上述稳定剂混合物的混合物在可聚合化合物的后处理、储存和/或运输过程中稳定可聚合化合物使之不发生聚合中的用途。
在本发明文中,可聚合化合物为具有至少一个烯属不饱和基团的那些。这些化合物选自一-、二-或三烯属不饱和C3-C8羧酸,这些一-、二-或三烯属不饱和C3-C8羧酸的C1-C20酯、C1-C20酰胺、C1-C20腈和C1-C20酸酐,至多20个碳原子的羧酸的乙烯酯,1-10个碳原子的醇的乙烯基醚,至多20个碳原子的乙烯基芳族和乙烯基杂芳族化合物,环上具有3-10个碳原子的乙烯基内酰胺,开链N-乙烯基酰胺化合物和N-乙烯基胺化合物,乙烯基卤化物,具有2-8个碳原子和1或2个双键的任选卤化的脂族烃,亚乙烯基类化合物或这些单体的混合物。
优选的一-、二-或三烯属不饱和C3-C6羧酸例如为(甲基)丙烯酸、二甲基丙烯酸、乙基丙烯酸、柠康酸、亚甲基丙二酸、丁烯酸、富马酸、中康酸、衣康酸、马来酸及其C1-C20烷基酯、C1-C20酰胺、C1-C20腈、C1-C20醛和C1-C20酸酐,例如(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸正丙酯、(甲基)丙烯酸异丙酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸芳酯、马来酸单甲酯、马来酸二甲酯、马来酸单乙酯、马来酸二乙酯、(甲基)丙烯酸亚烷基二醇酯、(甲基)丙烯酰胺、N-二甲基(甲基)丙烯酰胺、N-叔丁基(甲基)丙烯酰胺、(甲基)丙烯腈、(甲基)丙烯醛、(甲基)丙烯酸酐、衣康酸酐、马来酸酐及其单酯。这类的阳离子单体例如为(甲基)丙烯酸二烷基氨基烷基酯和二烷基氨基烷基(甲基)丙烯酰胺如(甲基)丙烯酸二甲基氨基甲酯、(甲基)丙烯酸二甲基氨基乙酯、(甲基)丙烯酸二乙基氨基乙酯以及最后提及的单体与羧酸或无机酸的盐和季铵化产物的盐。
这类的其它单体例如为含羟基单体,尤其为(甲基)丙烯酸C1-C10羟基烷基酯如(甲基)丙烯酸羟乙酯、(甲基)丙烯酸羟丙酯、(甲基)丙烯酸羟丁酯和(甲基)丙烯酸羟异丁酯。
这类的其它单体为单(甲基)丙烯酸苯氧乙基乙二醇酯、(甲基)丙烯酸缩水甘油酯、三丙烯酸三羟甲基丙酯、甲基丙烯酸脲基甲酯、(甲基)丙烯酸氨酯,如(甲基)丙烯酸2-氨基乙酯。
1-20个碳原子的羧酸的乙烯酯为例如月桂酸乙烯酯、硬脂酸乙烯酯、丙酸乙烯酯、支链烷烃羧酸乙烯酯和乙酸乙烯酯。
1-10个碳原子的醇的乙烯基醚的实例为甲基·乙烯基醚、乙基·乙烯基醚、丁基·乙烯基醚、4-羟丁基·乙烯基醚、乙烯基·异丁基醚和十二烷基·乙烯基醚。
适合的乙烯基芳族和乙烯基杂芳族化合物的实例为乙烯基甲苯、α-和对甲基苯乙烯、α-丁基苯乙烯、4-正丁基苯乙烯、4-正癸基苯乙烯、苯乙烯、二乙烯基苯、2-乙烯基吡啶、N-乙烯基咪唑、N-乙烯基哌啶酮、N-乙烯基-2-甲基咪唑和N-乙烯基-4-甲基咪唑。
环上具有3-10个碳原子的乙烯基内酰胺例如为N-乙烯基己内酰胺、N-乙烯基吡咯烷酮、月桂内酰胺、氧化嘌呤如黄嘌呤或其衍生物如3-甲基黄嘌呤、次黄嘌呤、鸟嘌呤、茶碱、咖啡因、腺嘌呤或可可碱。
此外,开链N-乙烯基酰胺化合物和N-乙烯基胺化合物,例如N-乙烯基甲酰胺、N-乙烯基-N-甲基甲酰胺、N-乙烯基乙酰胺、N-乙烯基-N-甲基乙酰胺、N-乙烯基-N-乙基乙酰胺、N-乙烯基丙酰胺、N-乙烯基-N-甲基丙酰胺与N-乙烯基丁酰胺和N-乙烯基-N-二甲基胺、N-乙烯基-N-甲基乙基胺、N-乙烯基-N-二乙基胺可由所述本发明方法稳定。
乙烯基卤化物为由氯、氟或溴取代的烯属不饱和化合物,例如氯乙烯、氟乙烯和偏二氯乙烯。
具有2-8个碳原子和1或2个烯属双键的任选卤化的脂族烃的实例为乙烯、丙烯、1-丁烯、2-丁烯、异丁烯、丁二烯、异戊二烯和氯丁二烯。
亚乙烯基类化合物的实例为二氰亚乙烯。
其它可聚合化合物为N-乙烯己内酰胺、乙烯基磷酸、乙烯基乙酸、烯丙基乙酸、N-乙烯基咔唑、羟甲基乙烯基酮、N,N-二乙烯基亚乙基脲、碳酸亚乙烯酯、四氟乙烯、六氟丙烯、硝基乙烯、α-氯丙烯酸酯、α-氰基丙烯酸酯、丙二酸亚甲酯、α-氰基山梨酸酯、环戊二烯、环戊烯、环己烯和环十二碳烯。
在本发明方法的优选实施方案中,自由基清除剂用来稳定一-、二-或三烯属不饱和C3-C8羧酸及其C1-C20烷基酯或N-乙烯基己内酰胺、N-乙烯基甲酰胺、N-乙烯基咪唑、N-乙烯基吡咯烷酮、乙烯基磷酸、N-乙烯基咔唑、N,N-二乙烯基亚乙基脲、丙烯酸三羟甲基丙酯、甲基丙烯酸脲基甲酯、苯乙烯、丁二烯或异戊二烯。
优选的不饱和C3-C8羧酸例如为丙烯酸和甲基丙烯酸及其C1-C8烷基酯,如(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丁酯和(甲基)丙烯酸2-乙基己酯。
在优选的实施方案中,本发明自由基清除剂用于如DE-A 100 64 642所述的方法中。为此,在至少一种稳定剂存在下后处理(甲基)丙烯酸的方法中,将源于该后处理过程且基本上不含(甲基)丙烯酸的含稳定剂的混合物供入蒸馏装置并且将由该装置获得的含稳定剂的低沸点料流再循环至后处理过程中。
特别适合所述方法的本发明自由基清除剂为在141℃(丙烯酸的沸点)和大气压力下其蒸汽压至少为15hPa,优选20-800hPa,特别优选25-500hPa,非常特别优选25-250hPa,尤其25-160hPa的那些及其混合物。
在更优选的实施方案中,将本发明自由基清除剂用于后处理N-乙烯基单体如所述乙烯酯、乙烯基醚、乙烯基芳族和乙烯基杂芳族化合物、开链N-乙烯酰胺化合物和N-乙烯基胺化合物的方法中。
当然,本发明方法的应用领域也涉及这些可聚合化合物的储存和运输。
在本文中使用的ppm与百分数的数据以重量计,另有说明的除外。
下述实施例阐述本发明,但本发明不局限于这些。
实施例1
在空气气氛下,将经双重蒸馏以除去储存稳定剂的0.5ml新鲜解冻的丙烯酸充入1.8ml的安瓿中。
将试样在120℃下存放在通循环气的干燥器中。
在每组测试系列中,将3个安瓿都充满丙烯酸试样并测试,并肉眼测定完全聚合所花费时间的平均值。
在一组测试系列中的平均标准差为约2-4%。
浓度为25ppm的自由基清除剂加上10ppm的吩噻嗪(PTZ),另有说明的除外。
由含有自自由基清除剂与PTZ的试样的聚合所花费时间与参比样的聚合所花费时间的商来计算相对效率。使用的参比样为纯PTZ,因此参比样的相对效率为1.0。
结果汇集于表3中。
表3
实施例2
将含有所需量稳定剂的90ml单体引入250ml的圆底烧瓶中并且用相应气氛吹扫。将烧瓶加热至所需的存放温度。以规定的时间间隔提取试样。用拉曼光谱法(Raman spectroscopy)研究聚合物的含量。相对于未经稳定化试样的曲线显示了所使用的稳定剂体系的效率。
将N-乙烯基吡咯烷酮(NVP)与吡咯烷酮的混合物(1∶1)用作参考,且在其中加入25ppm的PTZ。在150℃下和在空气气氛中研究试样。发生聚合物快速形成(PVP=聚乙烯基吡咯烷酮)。
结果显示于表4。
时间(分钟) | PVP(重量%)25ppm PTZ |
0 | 0.0 |
15 | 4.4 |
30 | 9.4 |
45 | 13.1 |
60 | 16.6 |
75 | 19.0 |
90 | 21.8 |
105 | 23.6 |
120 | 25.0 |
135 | 27.4 |
150 | 29.2 |
165 | 30.8 |
180 | 32.7 |
在每种情况下将25ppm的自由基清除剂(来自实施例1的表3)与25ppm的PTZ的混合物加入N-乙烯基吡咯烷酮与吡咯烷酮的混合物(1∶1)中并在相同条件下加热。不能测得实施例1中所使用的自由基清除剂之间有显著差异。一种自由基清除剂(来自实施例1的表3,第一入口)的结果汇集于表5。在本发明自由基清除剂和PTZ的存在下成功抑制了PVP的形成。
时间(分钟) | PVP(重量%)25ppm PTZ25ppm Rs1) |
0 | 0.0 |
15 | 0.3 |
30 | 0.1 |
45 | 0.2 |
60 | 0.7 |
75 | 0.3 |
90 | 0.5 |
105 | 0.7 |
120 | 1.1 |
135 | 2.0 |
150 | 1.5 |
165 | 2.3 |
180 | 2.7 |
1)Rs=自由基清除剂
基于该实施例,然后研究了不同浓度的PTZ和本发明自由基清除剂的效果。结果示于表6。从该表中可明显看出,在每种情况下检测不到25ppm的PTZ和自由基清除剂的量在抑制聚合中的显著差异。
时间(分钟) | PVP(重量%)未稳定化 | PVP(重量%)12.5ppm PTZ12.5ppm Rs1) | PVP(重量%)25ppm PTZ25ppm Rs1) | PVP(重量%)50ppm PTZ50ppm Rs1) | PVP(重量%)100ppm PTZ100ppm Rs1) |
0 | 0.6 | 0.4 | 0.0 | 0.1 | 0.3 |
15 | 35.2 | 1.1 | 0.3 | 0.0 | 0.0 |
30 | 42.1 | 1.9 | 0.1 | 0.3 | 0.2 |
45 | 46.2 | 2.9 | 0.2 | 0.1 | 0.2 |
60 | 48.1 | 5.2 | 0.7 | 0.4 | 0.6 |
75 | 49.7 | 5.6 | 0.3 | 0.5 | 0.7 |
90 | 50.1 | 6.5 | 0.5 | 1.0 | 0.6 |
105 | 51.2 | 7.7 | 0.7 | 0.8 | 0.9 |
120 | 51.8 | 7.9 | 1.1 | 1.2 | 1.0 |
135 | 52.6 | 8.7 | 2.0 | 1.4 | 1.5 |
150 | 53.2 | 9.0 | 1.5 | 1.1 | 1.9 |
165 | 53.3 | 9.3 | 2.3 | 1.3 | 2.1 |
180 | 54.1 | 9.7 | 2.7 | 1.8 | 2.7 |
1)Rs=自由基清除剂
Claims (23)
1.一种在后处理、储存和/或运输过程中稳定可聚合化合物使之不发生聚合的方法,其中使用至少一种含有至少两个甘氨酸单元的自由基清除剂,前提条件为该自由基清除剂不选自乙二胺四乙酸(EDTA)、二亚乙基三胺五乙酸(DTPA)、反式1,2-环己二胺四乙酸(CYDTA)及其碱金属与碱土金属盐。
3.根据权利要求1或2的方法,其中使用至少一种含有至少两个甘氨酸单元和至少一个酰胺和/或酯单元的自由基清除剂。
4.根据权利要求1-3中任一项的方法,其中使用至少一种式(I)的自由基清除剂,
其中G1可以为NR3R4或OR7,
G2可以为NR5R6或OR8,
R1-R6可以互相独立地为氢、C1-C20烷基、C1-C20烷基羰基、C2-C20链烯基、C2-C20链烯基羰基、C2-C20炔基、C2-C20炔基羰基、C3-C15环烷基、C5-C15环烷基羰基、芳基、芳基羰基或杂环,
R7和R8可以互相独立地为C1-C20烷基、C1-C20烷基羰基、C2-C20链烯基、C2-C20链烯基羰基、C2-C20炔基、C2-C20炔基羰基、C3-C15环烷基、C5-C15环烷基羰基、芳基、芳基羰基或杂环,
X可以为C1-C20烷基、NCH2COOR9、NR10、O、S、PR11、Se、SiOR12R13或芳基,其中R9-R13可以互相独立地为氢或C1-C20烷基,和
k、l、m和n可以互相独立地为0-20的数值。
5.根据权利要求1-4中任一项的方法,其中R1和R2相同并且为氢或C1-C20烷基。
6.根据权利要求1-5中任一项的方法,其中R3和R5相同并且为氢、C1-C20烷基或C1-C20烷基羰基。
7.根据权利要求1-6中任一项的方法,其中R4和R6相同并且为C1-C20烷基、C1-C20烷基羰基、芳基、C2-C20链烯基、C2-C20链烯基羰基、C2-C20炔基或C2-C20炔基羰基。
8.根据权利要求6或7的方法,其中R3和R5为氢并且R4和R6选自苯基、苄基、对甲氧基苯基、邻羟基苯基、间羟基苯基、对羟基苯基、1-羟己基、甲基、乙基、丙基、丁基、乙二醇、二甘醇、三甘醇、具有4-10个EO单元的乙氧基化物、乙二胺、二亚乙基三胺、三亚乙基四胺和氨基酸。
9.根据权利要求1-5中任一项的方法,其中R7和R8相同并且为C1-C20烷基、C1-C20烷基羰基、芳基、C2-C20链烯基、C2-C20链烯基羰基、C2-C20炔基或C2-C20炔基羰基。
10.根据权利要求9的方法,其中R7和R8选自苯基、苄基、对甲氧基苯基、邻羟基苯基、间羟基苯基、对羟基苯基、1-羟己基、甲基、乙基、丙基、丁基、乙二醇、二甘醇、具有4-10个EO单元的乙氧基化物、乙二胺、二亚乙基三胺、三亚乙基四胺和氨基酸。
11.根据权利要求1-10中任一项的方法,其中X为C1-C20烷基或CH2NCOOR9。
13.根据权利要求1-12中任一项的方法,其中基于可聚合化合物,使用0.1-1000ppm的自由基清除剂或自由基清除剂混合物。
14.根据权利要求1-13中任一项的方法,其中使用至少一种共稳定剂。
15.根据权利要求14的方法,其中所述共稳定剂选自含氧气体、酚类化合物、醌类和氢醌类化合物、N-氧基化合物、芳族胺、苯二胺、亚胺、磺酰胺、肟、羟胺、脲衍生物、含磷化合物、含硫化合物、基于四氮杂轮烯的配合剂和金属盐,如果适合的话以及它们的混合物。
16.根据权利要求14或15的方法,其中将吩噻嗪、氢醌、氢醌单甲醚、2,2,6,6-四甲基哌啶-N-氧基、4-羟基-2,2,6,6-四甲基哌啶-N-氧基、4-氧代-2,2,6,6-四甲基哌啶-N-氧基、N,N′-二仲丁基-对苯二胺、乙酸铈(III)、乙基己酸铈(III)、含氧气体和/或其混合物用作共稳定剂。
17.根据上述权利要求中任一项的方法,其中可聚合化合物含有至少一个烯属不饱和基团。
18.根据权利要求17的方法,其中可聚合化合物选自一-、二-或三烯属不饱和C3-C8羧酸,这些一-、二-或三烯属不饱和C3-C8羧酸的C1-C20酯、C1-C20酰胺、C1-C20腈和C1-C20酸酐,含有至多20个碳原子的羧酸的乙烯酯、含有1-10个碳原子的醇的乙烯基醚、至多20个碳原子的乙烯基芳族和乙烯基杂芳族化合物、环上具有3-10个碳原子的乙烯基内酰胺,开链N-乙烯基酰胺化合物和N-乙烯基胺化合物、乙烯基卤化物、具有2-8个碳原子和1或2个双键的并且如果合适的话卤化的脂族烃、亚乙烯基类化合物或这些单体的混合物。
19.根据权利要求17或18的方法,其中将一-、二-或三烯属不饱和C3-C8羧酸,这些一-、二-或三烯属不饱和C3-C8羧酸的C1-C20酯,含有至多20个碳原子的羧酸的乙烯酯、含有1-10个碳原子的醇的乙烯基醚,至多20个碳原子的乙烯基芳族和乙烯基杂芳族化合物、环上具有3-10个碳原子的乙烯基内酰胺、开链N-乙烯基酰胺化合物或N-乙烯基胺化合物用作可聚合化合物。
20.根据权利要求17-19中任一项的方法,其中将(甲基)丙烯酸、(甲基)丙烯酸酯、N-乙烯基己内酰胺、N-乙烯基甲酰胺、N-乙烯基咪唑、N-乙烯基吡咯烷酮、乙烯基磷酸、N-乙烯咔唑、N,N-二乙烯基亚乙基脲、三丙烯酸三羟甲基丙酯、甲基丙烯酸脲基甲酯、苯乙烯、丁二烯或异戊二烯用作可聚合化合物。
21.一种稳定剂混合物,包含:
i)至少一种含有至少两个甘氨酸单元的自由基清除剂,前提条件为该自由基清除剂不选自乙二胺四乙酸(EDTA)、二亚乙基三胺五乙酸(DTPA)、反式1,2-环己二胺四乙酸(CYDTA)及其碱金属与碱土金属盐,和
ii)至少一种其它稳定剂或共稳定剂。
22.一种包含如权利要求21的稳定剂混合物和至少一种可聚合化合物的混合物。
23.如权利要求21的稳定剂混合物在后处理、储存和/或运输过程中稳定可聚合化合物使之不发生聚合的用途。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP03021803.6 | 2003-09-26 | ||
EP03021803A EP1518916A1 (de) | 2003-09-26 | 2003-09-26 | Radikalfänger als stabilisatoren polymerisationsfähiger Verbindungen |
DE10346135.3 | 2003-10-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1878852A true CN1878852A (zh) | 2006-12-13 |
Family
ID=34178505
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNA2004800330735A Pending CN1878852A (zh) | 2003-09-26 | 2004-09-18 | 用作可聚合化合物的稳定剂的自由基捕集剂 |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP1518916A1 (zh) |
CN (1) | CN1878852A (zh) |
ZA (1) | ZA200603260B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN117431054A (zh) * | 2023-11-01 | 2024-01-23 | 滨州乾坤化工机械有限公司 | 一种酸化压裂液用高温铁离子稳定剂及其制备方法 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006118330A1 (en) * | 2005-04-28 | 2006-11-09 | Nippon Shokubai Co., Ltd. | Composition of n-alkenyl carboxylic acid tertiary amide |
GB201317423D0 (en) | 2013-10-02 | 2014-09-17 | Pb Clermont Sa | Stabilized nitrocellulose based propellant composition |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH569405A5 (en) * | 1972-07-11 | 1975-11-28 | Ciba Geigy Ag | Combatting metal deficiency in biological systems - with metal chelates of ethylene diamine tetraacetic acid diamide derivs |
FR2639640B1 (fr) * | 1988-11-25 | 1992-07-24 | Rhone Poulenc Chimie | Procede pour retarder la gelification de monomeres insatures, compositions a gelification retardee contenant lesdits monomeres et application desdites compositions au traitement de formations souterraines |
DE19920796A1 (de) * | 1999-05-06 | 2000-11-09 | Roehm Gmbh | Verfahren zur Herstellung von Isobornylmethacrylat |
DE10105014C2 (de) * | 2001-01-26 | 2003-03-27 | Schering Ag | Neues Verfahren zur Herstellung von Monoamiden der DTPA |
-
2003
- 2003-09-26 EP EP03021803A patent/EP1518916A1/de not_active Withdrawn
-
2004
- 2004-09-18 CN CNA2004800330735A patent/CN1878852A/zh active Pending
-
2006
- 2006-04-24 ZA ZA200603260A patent/ZA200603260B/en unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN117431054A (zh) * | 2023-11-01 | 2024-01-23 | 滨州乾坤化工机械有限公司 | 一种酸化压裂液用高温铁离子稳定剂及其制备方法 |
CN117431054B (zh) * | 2023-11-01 | 2024-04-16 | 滨州乾坤化工机械有限公司 | 一种酸化压裂液用高温铁离子稳定剂及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
ZA200603260B (en) | 2007-07-25 |
EP1518916A1 (de) | 2005-03-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8784537B2 (en) | Amine-containing absorption medium, process and apparatus for absorption of acidic gases from gas mixtures | |
JP3835843B2 (ja) | 純粋グレードのアクリル酸の製造方法 | |
US9878285B2 (en) | Method and absorption medium for absorbing CO2 from a gas mixture | |
KR100368886B1 (ko) | 순수아크릴산의연속제조방법 | |
CN1469916A (zh) | 作为聚合抑制剂的c-亚硝基苯胺化合物及其共混物 | |
CN1402697A (zh) | 不饱和单体的阻聚 | |
JP2015108028A (ja) | 純粋なトリエタノールアミン(teoa)の製造法 | |
JP4556491B2 (ja) | 重合禁止剤、これを含有する組成物、及び前記重合禁止剤を用いる易重合性化合物の製造方法 | |
KR20060136430A (ko) | 히드로시안화 방법 | |
KR20070000460A (ko) | 히드로시안화 방법 | |
KR20150133860A (ko) | 아크릴산 및 아크릴레이트 공정에서 중합 및 오염의 억제방법 | |
CN1832790A (zh) | 萃取蒸馏中产生的离子液体的再循环 | |
CN1156493C (zh) | 立即终止自由基聚合反应的方法 | |
CN1213030C (zh) | 不饱和单体聚合的抑制 | |
CN101155779B (zh) | N-乙烯基-2-吡咯烷酮的生产方法 | |
JP6393288B2 (ja) | 早期重合の防止方法 | |
CN1878852A (zh) | 用作可聚合化合物的稳定剂的自由基捕集剂 | |
JP2011063607A (ja) | 不飽和モノニトリル類の回収及び精製中に重合を阻止する方法 | |
KR100809877B1 (ko) | 초고순도 알킬렌카보네이트의 정제 방법 | |
JP3412167B2 (ja) | N−ビニルホルムアミド組成物 | |
CN1863760A (zh) | 精馏分离含丙烯酸的液体的方法 | |
US20060287548A1 (en) | Radical interceptors as stabilizers of polymerizable compounds | |
CN109071421A (zh) | 减少二腈流中的cpi的方法 | |
JP2023043050A (ja) | 新規アミン化合物、酸性ガス吸収剤、酸性ガスの除去方法及び酸性ガス除去 | |
JP2005343845A (ja) | アクリロニトリルの重合抑制剤および重合抑制方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
WD01 | Invention patent application deemed withdrawn after publication |