CN115819238A - 一种低迁移受阻酚抗氧化合物、制备方法及组合物 - Google Patents
一种低迁移受阻酚抗氧化合物、制备方法及组合物 Download PDFInfo
- Publication number
- CN115819238A CN115819238A CN202211316611.8A CN202211316611A CN115819238A CN 115819238 A CN115819238 A CN 115819238A CN 202211316611 A CN202211316611 A CN 202211316611A CN 115819238 A CN115819238 A CN 115819238A
- Authority
- CN
- China
- Prior art keywords
- compound
- tert
- butyl
- chr
- hydroxyphenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 171
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 56
- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 41
- 230000003078 antioxidant effect Effects 0.000 title claims abstract description 32
- 239000000203 mixture Substances 0.000 title claims abstract description 22
- 238000013508 migration Methods 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000005012 migration Effects 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- -1 cumyl Chemical group 0.000 claims description 50
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 229920000877 Melamine resin Polymers 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
- 230000032050 esterification Effects 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000005457 optimization Methods 0.000 claims description 4
- 238000005809 transesterification reaction Methods 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001721 carbon Chemical class 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 150000007974 melamines Chemical class 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 150000003918 triazines Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000002184 metal Chemical group 0.000 claims 1
- 229910052751 metal Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 150000002926 oxygen Chemical group 0.000 claims 1
- 238000000605 extraction Methods 0.000 abstract description 11
- 229920000642 polymer Polymers 0.000 abstract description 6
- 238000010525 oxidative degradation reaction Methods 0.000 abstract description 2
- 150000002989 phenols Chemical class 0.000 abstract description 2
- 238000012545 processing Methods 0.000 abstract description 2
- 238000000034 method Methods 0.000 description 52
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 17
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- TXBWKXFDLINCMJ-UHFFFAOYSA-N 2,6-ditert-butyl-4-(chloromethyl)phenol Chemical compound CC(C)(C)C1=CC(CCl)=CC(C(C)(C)C)=C1O TXBWKXFDLINCMJ-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- 150000003077 polyols Chemical class 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000002530 phenolic antioxidant Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- ICSHBDAVNHZUCZ-UHFFFAOYSA-N 2,4-ditert-butyl-6-(chloromethyl)phenol Chemical compound CC(C)(C)C1=CC(CCl)=C(O)C(C(C)(C)C)=C1 ICSHBDAVNHZUCZ-UHFFFAOYSA-N 0.000 description 3
- PDOJSYBPSAIIIU-UHFFFAOYSA-N 4-tert-butyl-2-(2-phenylpropan-2-yl)phenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C=2C=CC=CC=2)=C1 PDOJSYBPSAIIIU-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000006289 hydroxybenzyl group Chemical group 0.000 description 3
- 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 3
- 229920000570 polyether Polymers 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 230000009469 supplementation Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- WLQJKVRXZQCVGS-UHFFFAOYSA-N 4-tert-butyl-2-(chloromethyl)-6-methylphenol Chemical compound Cc1cc(cc(CCl)c1O)C(C)(C)C WLQJKVRXZQCVGS-UHFFFAOYSA-N 0.000 description 2
- PXMJCECEFTYEKE-UHFFFAOYSA-N Benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, methyl ester Chemical compound COC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PXMJCECEFTYEKE-UHFFFAOYSA-N 0.000 description 2
- BFTVLJLQGVJILM-UHFFFAOYSA-N CC(C)(C)C(C=C1C(C)(C)C)=CC(CC2=CC(CCC(Cl)=O)=CC(C(C)(C)C)=C2O)=C1O Chemical compound CC(C)(C)C(C=C1C(C)(C)C)=CC(CC2=CC(CCC(Cl)=O)=CC(C(C)(C)C)=C2O)=C1O BFTVLJLQGVJILM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- QKGLDJYQVIAMNN-UHFFFAOYSA-N OC(=O)CCC1=CC(CC2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2O)=C(O)C(C(C)(C)C)=C1 Chemical compound OC(=O)CCC1=CC(CC2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2O)=C(O)C(C(C)(C)C)=C1 QKGLDJYQVIAMNN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 125000005252 haloacyl group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 125000003431 oxalo group Chemical group 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 150000008301 phosphite esters Chemical class 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 229920006324 polyoxymethylene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 125000004079 stearyl 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])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])[H] 0.000 description 2
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 2
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- OQBLGYCUQGDOOR-UHFFFAOYSA-L 1,3,2$l^{2}-dioxastannolane-4,5-dione Chemical compound O=C1O[Sn]OC1=O OQBLGYCUQGDOOR-UHFFFAOYSA-L 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 1
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-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
- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-UHFFFAOYSA-N 0.000 description 1
- BPZIYBJCZRUDEG-UHFFFAOYSA-N 2-[3-(1-hydroxy-2-methylpropan-2-yl)-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]-2-methylpropan-1-ol Chemical compound C1OC(C(C)(CO)C)OCC21COC(C(C)(C)CO)OC2 BPZIYBJCZRUDEG-UHFFFAOYSA-N 0.000 description 1
- KPJKMUJJFXZGAX-UHFFFAOYSA-N 2-chloropropan-2-ylbenzene Chemical compound CC(C)(Cl)C1=CC=CC=C1 KPJKMUJJFXZGAX-UHFFFAOYSA-N 0.000 description 1
- KTXWGMUMDPYXNN-UHFFFAOYSA-N 2-ethylhexan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-] KTXWGMUMDPYXNN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GJAPTYIPALRUHT-UHFFFAOYSA-N 3,5-ditert-butyl-2-hydroxybenzoyl chloride Chemical group CC(C)(C)C1=CC(C(Cl)=O)=C(O)C(C(C)(C)C)=C1 GJAPTYIPALRUHT-UHFFFAOYSA-N 0.000 description 1
- AIPCSKRJJOUNEM-UHFFFAOYSA-N 3,5-ditert-butyl-4-hydroxybenzoyl chloride Chemical compound CC(C)(C)C1=CC(C(Cl)=O)=CC(C(C)(C)C)=C1O AIPCSKRJJOUNEM-UHFFFAOYSA-N 0.000 description 1
- WGKYSFRFMQHMOF-UHFFFAOYSA-N 3-bromo-5-methylpyridine-2-carbonitrile Chemical compound CC1=CN=C(C#N)C(Br)=C1 WGKYSFRFMQHMOF-UHFFFAOYSA-N 0.000 description 1
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- NEBBWIDWDVTMDG-UHFFFAOYSA-N C(=O)(CCC1=CC(CC2=CC(C)=C(O)C(C(C)(C)C)=C2)=C(O)C(C(C)(C)C)=C1)OC Chemical compound C(=O)(CCC1=CC(CC2=CC(C)=C(O)C(C(C)(C)C)=C2)=C(O)C(C(C)(C)C)=C1)OC NEBBWIDWDVTMDG-UHFFFAOYSA-N 0.000 description 1
- YHNWIZCEPSRWFP-UHFFFAOYSA-N C(C(=O)OC)CC1=CC(=C(C(CC2=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C2)=C1)O)C(C)(C)C Chemical compound C(C(=O)OC)CC1=CC(=C(C(CC2=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C2)=C1)O)C(C)(C)C YHNWIZCEPSRWFP-UHFFFAOYSA-N 0.000 description 1
- SQJJUYRLNSBYQI-UHFFFAOYSA-N C(C(=O)OC)CC1=CC(C(C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2O)O)=C(O)C(C(C)(C)C)=C1 Chemical compound C(C(=O)OC)CC1=CC(C(C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2O)O)=C(O)C(C(C)(C)C)=C1 SQJJUYRLNSBYQI-UHFFFAOYSA-N 0.000 description 1
- UDJNZWBXWPREPF-UHFFFAOYSA-N C(C(=O)OC)CC1=CC(C(C2=CC(C)=CC(C(C)(C)C)=C2O)C)=C(O)C(C(C)(C)C)=C1 Chemical compound C(C(=O)OC)CC1=CC(C(C2=CC(C)=CC(C(C)(C)C)=C2O)C)=C(O)C(C(C)(C)C)=C1 UDJNZWBXWPREPF-UHFFFAOYSA-N 0.000 description 1
- GNODLZDWCQMEOP-UHFFFAOYSA-N C(C(=O)OC)CC1=CC(CC2=C(C(=CC(C(C)(C)C)=C2)C(C)(C)C)O)=C(O)C(C(C)(C)C)=C1 Chemical compound C(C(=O)OC)CC1=CC(CC2=C(C(=CC(C(C)(C)C)=C2)C(C)(C)C)O)=C(O)C(C(C)(C)C)=C1 GNODLZDWCQMEOP-UHFFFAOYSA-N 0.000 description 1
- NXWQGALLLUBILB-UHFFFAOYSA-N C(C)(C1=C(O)C(C(C)(C)C)=CC(C(=O)C2=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=C2CCC(=O)OC)=C1)(C)C Chemical compound C(C)(C1=C(O)C(C(C)(C)C)=CC(C(=O)C2=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=C2CCC(=O)OC)=C1)(C)C NXWQGALLLUBILB-UHFFFAOYSA-N 0.000 description 1
- DRVDYAKTVLVOQE-UHFFFAOYSA-N C(CC1=CC(C(=O)C2=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C2)=C(O)C(C(C)(C)C)=C1)C(=O)OC Chemical compound C(CC1=CC(C(=O)C2=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C2)=C(O)C(C(C)(C)C)=C1)C(=O)OC DRVDYAKTVLVOQE-UHFFFAOYSA-N 0.000 description 1
- KPWZMHDZYVDXIW-UHFFFAOYSA-N CC(C)(C)C(C=C(CCC(NCCCNC(CCC(C=C1CC(C=C2C(C)(C)C)=CC(C(C)(C)C)=C2O)=CC(C(C)(C)C)=C1O)=O)=O)C=C1CC(C=C2C(C)(C)C)=CC(C(C)(C)C)=C2O)=C1O Chemical compound CC(C)(C)C(C=C(CCC(NCCCNC(CCC(C=C1CC(C=C2C(C)(C)C)=CC(C(C)(C)C)=C2O)=CC(C(C)(C)C)=C1O)=O)=O)C=C1CC(C=C2C(C)(C)C)=CC(C(C)(C)C)=C2O)=C1O KPWZMHDZYVDXIW-UHFFFAOYSA-N 0.000 description 1
- YZPPKPUDSIASTO-UHFFFAOYSA-N CC(C)(C)C(C=C(CCC(OC)=O)C=C1C(C(C=C2C(C)(C)C)=CC(C(C)(C)C)=C2O)O)=C1O Chemical compound CC(C)(C)C(C=C(CCC(OC)=O)C=C1C(C(C=C2C(C)(C)C)=CC(C(C)(C)C)=C2O)O)=C1O YZPPKPUDSIASTO-UHFFFAOYSA-N 0.000 description 1
- XLGTUAWDJOJGKJ-UHFFFAOYSA-N CC(C)(C)C(C=C(CCl)C=C1C(C)(C)C2=CC=CC=C2)=C1O Chemical compound CC(C)(C)C(C=C(CCl)C=C1C(C)(C)C2=CC=CC=C2)=C1O XLGTUAWDJOJGKJ-UHFFFAOYSA-N 0.000 description 1
- KVYNEZMRKBWMNW-UHFFFAOYSA-N CC(C)(C)C(C=C1C(C)(C)C)=CC(C(CC2=CC=CC=C2)C2=C(CCC(OC)=O)C=C(C(C)(C)C)C(O)=C2)=C1O Chemical compound CC(C)(C)C(C=C1C(C)(C)C)=CC(C(CC2=CC=CC=C2)C2=C(CCC(OC)=O)C=C(C(C)(C)C)C(O)=C2)=C1O KVYNEZMRKBWMNW-UHFFFAOYSA-N 0.000 description 1
- BOZKHQNPMYDFJR-UHFFFAOYSA-N CC(C)(C)C(C=C1C(C)(C)C)=CC(CC2=CC(CCC(NCCCNC(CCC(C=C3CC(C=C(C(C)(C)C)C=C4C(C)(C)C)=C4O)=CC(C(C)(C)C)=C3O)=O)=O)=CC(C(C)(C)C)=C2O)=C1O Chemical compound CC(C)(C)C(C=C1C(C)(C)C)=CC(CC2=CC(CCC(NCCCNC(CCC(C=C3CC(C=C(C(C)(C)C)C=C4C(C)(C)C)=C4O)=CC(C(C)(C)C)=C3O)=O)=O)=CC(C(C)(C)C)=C2O)=C1O BOZKHQNPMYDFJR-UHFFFAOYSA-N 0.000 description 1
- REFZIICDSYFXSV-UHFFFAOYSA-N CC(C)(C)C(C=C1C(C)(C)C)=CC(CC2=CC(CCC(OC3=CC=CC=C3)=O)=CC(C(C)(C)C)=C2O)=C1O Chemical compound CC(C)(C)C(C=C1C(C)(C)C)=CC(CC2=CC(CCC(OC3=CC=CC=C3)=O)=CC(C(C)(C)C)=C2O)=C1O REFZIICDSYFXSV-UHFFFAOYSA-N 0.000 description 1
- YPOFIGJNYDNEDE-UHFFFAOYSA-N CC(C)(C)C1=CC(CC2=C(CCC(OC)=O)C=C(C(C)(C)C)C(O)=C2C(C)(C)C)=CC(C(C)(C)C)=C1O Chemical compound CC(C)(C)C1=CC(CC2=C(CCC(OC)=O)C=C(C(C)(C)C)C(O)=C2C(C)(C)C)=CC(C(C)(C)C)=C1O YPOFIGJNYDNEDE-UHFFFAOYSA-N 0.000 description 1
- SGANFJCJUFYPQS-UHFFFAOYSA-N CC(C)(C)C1=CC(CCC(OC)=O)=C(C(C(C=C2C(C)(C)C)=CC(C(C)(C)C)=C2O)Cl)C(C(C)(C)C)=C1O Chemical compound CC(C)(C)C1=CC(CCC(OC)=O)=C(C(C(C=C2C(C)(C)C)=CC(C(C)(C)C)=C2O)Cl)C(C(C)(C)C)=C1O SGANFJCJUFYPQS-UHFFFAOYSA-N 0.000 description 1
- IBIKHSOUZCNKES-UHFFFAOYSA-N CC(C1=C(O)C(C(C)(C)C)=CC(C(O)C2=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=C2CCC(=O)OC)=C1)(C)C Chemical compound CC(C1=C(O)C(C(C)(C)C)=CC(C(O)C2=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=C2CCC(=O)OC)=C1)(C)C IBIKHSOUZCNKES-UHFFFAOYSA-N 0.000 description 1
- ONORNIAZAHIOTD-UHFFFAOYSA-N CCCCCCCCCCCCSCC1=CC(CC(CCCCC(CC(C=C2CSCCCCCCCCCCCC)=CC(CC(C=C3C(C)(C)C)=CC(C(C)(C)C)=C3O)=C2O)C(O)=O)C(O)=O)=CC(CC(C=C2C(C)(C)C)=CC(C(C)(C)C)=C2O)=C1O Chemical compound CCCCCCCCCCCCSCC1=CC(CC(CCCCC(CC(C=C2CSCCCCCCCCCCCC)=CC(CC(C=C3C(C)(C)C)=CC(C(C)(C)C)=C3O)=C2O)C(O)=O)C(O)=O)=CC(CC(C=C2C(C)(C)C)=CC(C(C)(C)C)=C2O)=C1O ONORNIAZAHIOTD-UHFFFAOYSA-N 0.000 description 1
- JOOVQRKONUYIOE-UHFFFAOYSA-N CCCCCCCCCCCCSCC1=CC(CCC(OC)=O)=CC(CC(C=C(C(C)(C)C)C=C2)=C2O)=C1O Chemical compound CCCCCCCCCCCCSCC1=CC(CCC(OC)=O)=CC(CC(C=C(C(C)(C)C)C=C2)=C2O)=C1O JOOVQRKONUYIOE-UHFFFAOYSA-N 0.000 description 1
- FLOWDDWCKDEPEY-UHFFFAOYSA-N CCCCCCCCCCCCSCC1=CC(CCC(OC)=O)=CC(CC(C=C2C(C)(C)C)=CC(C(C)(C)C)=C2O)=C1O Chemical compound CCCCCCCCCCCCSCC1=CC(CCC(OC)=O)=CC(CC(C=C2C(C)(C)C)=CC(C(C)(C)C)=C2O)=C1O FLOWDDWCKDEPEY-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- JCVVDFCBKLOQIG-UHFFFAOYSA-N O(C)C(=O)CCC1=CC(C(C2=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C2)C)=C(O)C(C(C)(C)C)=C1 Chemical compound O(C)C(=O)CCC1=CC(C(C2=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C2)C)=C(O)C(C(C)(C)C)=C1 JCVVDFCBKLOQIG-UHFFFAOYSA-N 0.000 description 1
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- WIHMDCQAEONXND-UHFFFAOYSA-M butyl-hydroxy-oxotin Chemical compound CCCC[Sn](O)=O WIHMDCQAEONXND-UHFFFAOYSA-M 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 239000012612 commercial material Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- RLJWTAURUFQFJP-UHFFFAOYSA-N propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)O.CC(C)O.CC(C)O RLJWTAURUFQFJP-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N tetraisopropyl titanate Substances CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/56—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having carbon atoms of carboxamide groups bound to carbon atoms of carboxyl groups, e.g. oxamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/26—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being saturated and containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C241/02—Preparation of hydrazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C243/30—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
- C07C243/32—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/56—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/32—Cyanuric acid; Isocyanuric acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/70—Other substituted melamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
- C08K5/1345—Carboxylic esters of phenolcarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1545—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/156—Heterocyclic compounds having oxygen in the ring having two oxygen atoms in the ring
- C08K5/1575—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34922—Melamine; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/375—Thiols containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/08—Polyurethanes from polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
本发明公开了一种低迁移受阻酚抗氧化合物、制备方法及组合物,聚合物在生产加工或使用中,会受到光、氧、热等因素的影响而发生降解。往往通过添加一种或多种常用抗氧剂来增加其抗氧化能力,以此抑制和延缓其氧化降解速率。传统受阻酚类抗氧化合物结构,在聚合物中会有迁移现象。本发明受阻酚类抗氧化合物,具有更多单元受阻酚,可实现低萃取、低迁移的目标。
Description
本申请是中国专利2020102220995一种低迁移受阻酚抗氧化合物、制备方法及组合物的分案申请,原申请的申请日2020-03-26;申请号2020102220995;发明创造名称:一种低迁移受阻酚抗氧化合物、制备方法及组合物。
技术领域
本发明涉及一种低迁移受阻酚抗氧化合物、制备方法及组合物。
背景技术
聚合物材料在生产加工及使用中往往会受到光、氧、热等因素的影响而发生降解,导致聚合物材料的物理、化学性能下降。因此聚合物材料往往通过添加一种或多种抗氧剂来增加其抗氧化能力。并以此抑制或延缓其氧化降解,延长其使用寿命。
其中受阻酚类化合物是最重要的抗氧化合物之一。受阻酚类抗氧剂在改善聚合物抗热氧老化性能方面已有广泛应用。
但传统受阻酚类抗氧化合物,在聚合物中会有迁移现象,严重影响效能。
传统受阻酚抗氧剂,例如2,4,6-三叔丁基苯酚(AO333)、二丁基羟基甲苯(BHT)、Irganox 1076。因为挥发性强,容易从聚合物内扩散迁移至表面,最终使聚合物中抗氧剂的含量消失,严重影响效能。且抗氧剂进入环境,破坏生态,对人体健康也有危害。
因此,设计具有耐迁移性的受阻酚抗氧剂具有重要意义。目前解决这些问题的方法之一是开发出多单元受阻酚抗氧剂,延缓迁移。例如Irganox 245是2单元受阻酚抗氧剂,例如Irganox 1330是3单元受阻酚抗氧剂,例如Irganox 1010是4单元受阻酚抗氧剂。然而单纯增加受阻酚抗氧剂分子量,并不一定能同时兼顾抗迁移和抗氧化性质。如何开发出更佳的具有抗迁移性质的多单元受阻酚抗氧剂,成为业者努力目标。
发明内容
目的:为解决现有技术的不足,本发明提供一种低迁移受阻酚抗氧化合物、制备方法及组合物,使得(受阻酚单元/分子量)的比值维持在最佳范围。该方法包括对(受阻酚单元数/分子量)做优化,使得优化后与优化前的(受阻酚单元数/分子量)比值大于1。也就是说,新增加的紧致的抗氧剂单元不至于让分子量增加太多。例如,本发明化合物10(实例10)和Eunox 1035(实例60)的(受阻酚单元数/分子量)的比值为(4/966):(2/642)=1.33(>1)。
令人惊讶地,这样的设计,大幅提高抗氧剂在树脂中的留存,也就是解决了传统受阻酚抗氧剂易迁移的缺点。
技术方案:为解决上述技术问题,本发明采用的技术方案为:
第一方面,提供一种式(I)化合物或其盐,
其中,R1-R7,是取代基团,R1-R2各自独立地选自含C1-C12较佳地,C1-C12,的烷基、苯基、苄基、枯基(cumyl)、C1-C12硫烷、C1-C2亚甲基C1-C12硫烷;R3-R4选自氢、含C1-C6的烷基、苯基、苄基、枯基、C1-C12硫烷、C1-C2亚甲基C1-C12硫烷。R5-R6各自独立地选自氢、羟基、卤素、羧基、含C1-C6烷基、羰基、酰基、酯基、C1-C6烷基胺基、C1-C6烷氧基、苯基、或R5-R6合为一酮基。较佳地,R1-R2各自独立地选自含C1-C5的烷基、苯基、苄基、枯基;R3-R4各自独立地选自氢、羟基、含C1-C5的烷基、羰基、酰基、C1-C5烷基胺基、C1-C5烷氧基;R5-R6各自独立地选自氢、羟基、含C1-C5的烷基、苯基。特佳地,R1-R2各自独立地选自甲基、叔丁基、枯基;R3-R4各自独立地选自氢、羟基、甲基、叔丁基;R5-R6各自独立地选自氢、羟基、含C1-C4的烷基。
R7是q价基团。较佳地,R7包括一键、氢、未取代或经取代的杂原子、未取代或经取代的碳或碳链、未取代或經取代的经氧或硫或氮所中断的碳链、碳环、杂环。更佳地,碳是一级到四级碳,碳链是C1-C20碳链,经氧或硫或氮所中断的碳链,可以是非聚合的C1-C20杂碳链或是包含多个聚合单元的链,例如聚乙二醇。较佳地,碳环为五到七元环,杂环为含氧或硫或氮的五到七元环。
更佳地,R7包括H、一键、(C)a(CH)b(CH2)c(CH3)d,其中(C)a和(CH)b和(CH2)c和(CH3)d之间的顺序可交错或互换,a~d不同时为0,a~d=0~18、(CH2CH2O)t H、(CH2CH2O)tOCH3、(CH)q-2(CH2)1~10(CH3)1~4,较佳地,(CH)q-2(CH2)1~10(CH3)1~3,其中(CH)q-2和(CH2)1~10和(CH3)1~3之间的顺序可交错或互换、S、SH、O、OH、N、NH、NHR8、P、Ca、Mg、Zn、Na、K、-(CHR8)1~18-、-(CH)q-2(CH2)1~18-,其中(CH)q-2和(CH2)1~18之间的顺序可交错或互换、-(C=O)1-4-、-(CHR8)u-、-(C=O)1-4(CHR8)u-,其中(C=O)1-4和(CHR8)u之间的顺序可交错或互换、-(CHR8)uS1-4(CHR8)u-、-(CHR8)uO1-4(CHR8)u-、-(CH2CH2O)tCH2CH2-、 三嗪类、三聚氰胺类、未经取代或经取代苯基或芐基、C1-C8环烷基;q≧a+b+c+d;t=1-20u=1-20。其中(CH)q-2和(CH2)1~18之间的顺序可互换,较佳地,-(CH)q-2(CH2)1~18-是-(CH2)1(CH)(CH2)1-或-(CH2)2(CH)(CH2)2-。较佳地,(C)a(CH)b(CH2)c(CH3)d,是C、CH、CH2、CH3,a~d=0-8,更佳地,a~d=0-4。较佳地,t=1-10。u=1-10。更佳地,t=1-5。u=1-5。
X是碳或杂原子,较佳地,选自选自N、NH、NHR8、O、S、CH2、CHR8,R8选自H、OH、含C1-C6的烷基,更佳地,X选自NH、O、CH2,特佳地,X=NH或O。
m=0-5、n=0-5、p=0-18、q=1-8、r=0-3、s=0-2。较佳地,m=0-2、n=0-2、p=0-18、q=1-6、r=0-1、s=0-1。更佳地,m=1、n=2、q=1-4、r=1、s=0。
特佳地,式(I)为以下结构:
R1-R7、m、n、X、p、r如上所定义。
特佳地,式(I)为以下结构:
R1-R7、m、n、X、p、q、r如上所定义。当R7=-(CH2CH2O)t CH2CH2-时,t>1。
特佳地,式(I)为以下结构:
R1-R7、m、n、X、p、q、r如上所定义。
式(I)所示化合物的制备方法,其特征在于,包括一酯化或转酯化反应如下:
其中,R1-R6、n、r、s如上所定义;-X(CH2)pR7是OH或离去基。较佳地,离去基是OCH3或卤素。
其中化合物(IV),由以下酯化或酯交换反应式所合成:
其中,R9是苯环上或非苯环上的可产生傅-克(Friedel-Crafts)烷基化或酰基化反应的基团,当R9是苯环上基团时,其包括卤素、C1-C8卤烷基、卤酰基、C1-C8卤酰基、C1-C8烯基。当R9是非苯环上基团时,其包括C1-C8烷基的醛或酮。
本发明反应,可以使用任何酯化或酯交换催化剂,较佳地,三异丙醇铝或锡化合物,特别是是二乙酸二丁基锡。可用于本发明实践的催化剂的例子包括辛酸亚锡,草酸亚锡,二月桂酸二丁基锡,二月桂酸二辛基酯,二丁基二辛基-2-乙基己酸酯,钛酸四异丙酯,钛酸四丁酯,钛酸四-2-乙基己酯,二丁基二呋喃基硫醇酯,二丁基二吲哚基辛基巯基乙酸盐,二月桂酸二丁基锡,二丁基氧化锡,丁基锡酸等。
本发明式(I)化合物,可用于组合物,提供抗氧化功能。组合物可应用于各种有机材料,例如但不限于多元醇或聚氨酯。多元醇在后续生产聚氨酯泡沫时过程中会释放大量热量,造成黄变,若添加一般抗氧化剂,因为抗氧化剂本身析出,也会造成黄变。本发明受阻酚抗氧剂适合各种材料,以尼龙-6树脂为例,100重量份计为0.1~5重量份。本发明的受阻酚类抗氧剂可与亚磷酸酯抗氧剂并用,受阻酚类抗氧剂与亚磷酸酯抗氧剂的混合重量比例,较佳为1∶4~1∶1。本发明的受阻酚类抗氧剂可也与其他安定剂并用,例如紫外线吸收剂、受阻胺等。
具体实施方式
下面结合实施例对本发明作进一步描述。以下实施例只是用于更加清楚地说明本发明的性能,而不能仅局限于下面的实施例。
本发明的受阻酚类抗氧剂,以实施例具体表示,但不限于实施例化合物。其中R7为一联结结构,例示如表1。
表1
表2
表3
实施例1
3-(3-叔丁基-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)丙酸甲酯
取25.4g的2,4-二叔丁基-6-氯甲基酚(化合物1.1)和23.6g的3-(3-(叔丁基)-4-羟基苯基)丙酸甲酯(CAS No 36837-50-0,mp=60℃),溶于200mL干燥的CH2Cl2,氮气下室温下搅拌,加入14g的AlCl3继续搅拌。TLC监控反应,其间补充AlCl3。反应完成后,混合物倒入200mL冰水中,搅拌,用CH2Cl2萃取3次。合并萃取相,依次用1%稀盐酸和盐水洗涤,无水硫酸钠干燥。蒸干溶剂,得到的残余物使用柱层析纯化,得到化合物(1)。MS(m/z)=454.3。H1-NMR(CDCl3),化学位移4.0,(aromatic carbon-CH2 -aromatic carbon)新生,说明化合物(1)被合成。
2,4-二叔丁基-6-氯甲基酚(化合物1.1)制法:在50ml反应瓶加入3g的2,4-二叔丁基苯酚(96-76-4)、0.6g的多聚甲醛、20克的乙酸、35%盐酸3克,升温到60℃,保温反应10个小时,取样监控反应。降温、水洗、烘干得化合物1.1。熔点:62℃。
实施例2
3-(3-叔丁基-5-(3,5-二叔丁基-2-羟基苯甲酰基)-4-羟基苯基)丙酸甲酯(2)
根据实施例1方法,但以3,5-二叔丁基-2-羟基苯甲酰氯,代替2,4-二叔丁基-6-氯甲基酚(化合物1.1),得到化合物(2),还原得到化合物(1)。化合物(2):MS(m/z)=468.3。C13-NMR(CDCl3),化学位移199.1,(aromatic-C(O)-aromatic)新生,说明化合物(2)被合成。
实施例3
3-(3-叔丁基-5-((3,5-二叔丁基-2-羟基苯基)(羟基)甲基)-4-羟基苯基)丙酸甲酯
100ml乙醇和10g化合物(2)混合物用冰水冷却,加入7.4g NaBH4,混合物保反应搅拌1hr完成。反应体系用冰乙酸中和至,然后真空条件下浓缩。浓缩物在CH2Cl2和水中进行分层,然后把有机相分出,用饱和盐水洗涤,用无水Na2SO4干燥后浓缩。得到化合物(3)。MS(m/z)=470.3。H1-NMR(CDCl3),化学位移6.2峰(aromatic carbon-HCOH-aromatic carbon)新生,说明化合物(3)被合成。
实施例4
3-(3-(叔丁基)-5-(1-(3-叔丁基-5–甲基-2-羟基苯基)乙基)-4-羟基苯基)丙酸甲酯
根据实施例1方法,但以乙醛代替聚甲醛,2-叔丁基-4-甲基酚代替2,4-二叔丁基酚,经层析法分离,得到化合物(4)。MS(m/z)=426.3。
实施例5
3-(3-(叔丁基)-5-(3-甲基-5-(叔丁基)-2-羟基苄基)-4-羟基苯基)丙酸甲酯
根据实施例1方法,但以2-(氯甲基)-4-(叔丁基)-6-甲基苯酚,代替2,4-二叔丁基酚,得到化合物(5)。MS(m/z)=412.3。
实施例6
3-(3-(叔丁基)-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)丙酸辛酯
将22.7g实施例1所制备的式(1)化合物,和10g辛醇(ExxonMobil Chemical)、0.2g三异丙醇铝(甲苯中)混合。将反应混合物搅拌并在氮气环境下85℃,升温,抽真空将生成的甲醇冷凝除去。监控反应,当反应完成,加入柠檬酸水溶液(50%),连续搅拌20分钟。然后,在75℃将水加入并搅拌20分钟。将有机相分离,然后用盐水洗涤两次,然后用硫酸钠干燥。接着甲苯和过量的辛醇减压下蒸馏出,将残留物真空干燥。经层析法分离,得到化合物(6)。MS(m/z)=552.4。
实施例7
3-(3-叔丁基-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)丙酸十八烷基酯
根据实施例6方法,但以硬脂醇代替辛醇,得到化合物(7)。MS(m/z)=692.6。
实施例8
2,5,8,11,14,17,20-七氧杂多糖-22-基-3-(3-(叔丁基)-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)丙酸酯
同实施例7方法,以Methoxypolyethylene glycol 350代替辛醇,产物经GPC纯化,得到化合物(8)。
实施例9
2-(2-(2-羟基乙氧基)乙氧基)乙基-3-(3-(叔丁基)-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)丙酸酯
根据实施例6方法,但以三甘醇(triethylene glycol),代替辛醇,控制三甘醇过量,得到化合物(9)和其二聚体。
实施例10
硫代双(乙烷-2,1-二基)双(3-(3-(叔丁基)-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)丙酸酯)(10)
根据根据实施例6方法,控制化合物(1)和二元醇类莫尔比2:1以上。使用100g化合物(1)和12.2g的2,2'-硫代二乙醇。得到化合物(10)。MS(m/z)=966.6。
实施例11
2-(2-(2-((3-(3-(叔丁基)-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)丙酰基)氧基)乙氧基)乙氧基)3-(3-(3,5-二叔丁基-2-羟基苄基)-4-羟基-5-甲基苯基)丙酸酯
根据根据实施例10方法,但使用化合物(1)和三甘醇(triethylene glycol)。得到化合物(11)。MS(m/z)=994.7。
实施例12
N,N'-(丙烷-1,3-二基)双(3-(3-叔丁基-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)丙酰胺)
取化合物(1)水解产物3-(3-(叔丁基)-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)丙酸(化合物19-1),66g(约1.5摩尔)、氯化亚砜27g(约2.25摩尔),于90℃反应3小时后,减压蒸出过量的二氯亚砜。得到3-(3-(叔丁基)-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)丙酰氯)(化合物12.2)。降温至60℃,加入甲苯100g,搅拌均匀。滴加由己二胺5.8g(0.5摩尔)、吡啶10g(1.25摩尔)和甲苯50克组成的混合液,控制温度小于60℃。滴完,升温至85℃,反应2小时。水洗后干燥,蒸去溶剂。经层析法分离,得到化合物(12)。MS(m/z)=960.7。
化合物(1)水解:将45.4g化合物(1),100ml甲醇,氮气下搅拌。60℃时开始滴加22ml的30% NaOH溶液。滴加完毕后,缓慢加热至65℃反应4h后,加入160mL的2N稀盐酸中和,搅拌2小时,水洗至中性、干燥后得到化合物(1)自由酸3-(3-(叔丁基)-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)丙酸)(化合物12-1)。
实施例13
1,6-二基双(3-(3-叔丁基-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)丙酸己酯)
根据根据实施例10方法,但使用化合物(1)和己二醇。得到化合物(13)。MS(m/z)=947.6。
实施例14
双(乙烷-2,1-二基)双(3-(3-叔丁基-5-(3,5-二叔丁基-2-羟基苄基))-4-羟基苯基)丙酸(草酰二(氮杂-二基))酯
根据根据实施例10方法,但使用化合物(1)和N.N′-二羟乙基草酰胺(1871-89-2,mp=168℃)。得到化合物(14)。MS(m/z)=1020.6。
实施例15
(2,4,8,10-四氧杂螺[5.5]十一烷-3,9-二基)双(2-甲基丙烷-2,1-二基)双(3-(3-(叔丁基)-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)丙酸酯)
根据根据实施例10方法,将化合物(1)和螺环乙二醇反应。得到化合物(15)。MS(m/z)=1148.8。螺环乙二醇,是工业原料2,2'-(2,4,8,10-四氧杂螺[5.5]十一烷-3,9-二基)双(2-甲基丙-1-醇)(mp=202℃)。
实施例16
3-(3-叔丁基-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)-N'-(3-(3-叔丁基-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)丙酰基)丙烷酰肼
根据实施例12方法,但以水合肼代替己二胺。得到化合物(16)。MS(m/z)=876.6。
实施例17
四(3-(3-(叔丁基)-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)苯丙酸季戊四醇酯
根据根据实施例10方法,但使用化合物(1)和季戊四醇。得到化合物(17)。MS(m/z)=1945.2。
实施例18
N,N”,N”-(1,3,5-三嗪-2,4,6-三基)三(3-(3-(叔丁基)-5-(3,5-二叔丁基-2-羟基苄基苄)-4-羟基苯基)丙酰胺)
根据实施例12方法,但以三聚氰胺代替己二胺。使用150g的3-(3-(叔丁基)-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)丙酰氯和12.6g的三聚氰胺。得到化合物(18)。MS(m/z)=1392.9。
实施例19
(2,4,6-三氧代-1,3,5-三嗪-1,3,5-三基)三(乙烷-2,1-二基)三(3-(3-(叔丁基)-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)丙酸酯)
根据实施例10方法,但使用150g化合物(1)和26g的三羟乙基异氰尿酸酯。三羟乙基异氰尿酸酯是工业原料(839-90-7,mp=136℃)。得到化合物(19)。MS(m/z)=1527.9。
实施例20
(2,4,6-三甲基苯-1,3,5-三基)三(亚甲基)三(3-(3-(叔丁基)-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)丙酸酯)
根据实施例10方法,但使用150g化合物(1)和21g的2,4,6-三甲基苯-1,3,5-三基)三甲醇。得到化合物(20)。MS(m/z)=1477.0。
实施例21
(一-六基苯)三(亚甲基)三(3-(3-(叔丁基)-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)丙酸酯)混合物
根据实施例10方法,但使用30g化合物(1)和2.6g的1,2,3,4,5,6六甲醇苯。得到混合物(21)。
实施例22
1,2,3-三(3-(3-(叔丁基)-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)丙酸苯酯)丙烷
根据实施例10方法,但使用150g化合物(1)和9.2g的丙三醇。得到化合物(22)。MS(m/z)=1358.9。
实施例23
3-(3-(叔丁基)-5-(3,5-二叔丁基-2-羟基苄基)-4-羟基苯基)丙酸钙
45.4g化合物(1),在醇类混合溶液200ml中,氮气下搅拌。滴加约100ml的5% NaOH溶液。滴加完毕后,缓慢加热至60℃,反应4小时。旋蒸去除去醇类溶剂,加入100ml乙酸乙酯萃取。取水层,滴加稀盐酸中和至pH=7-8,同时逐步加入0.5M二氯化钙水溶液,搅拌2小时,静置,过滤。碳酸钾水溶液清洗除去游离酸,水洗至中性、干燥后得到化合物(23)
实施例24
3-(3-(5-(叔丁基)-2-羟基-3-(2-苯基丙烷-2-基)苄基)-4-羟基-5-(2-苯基丙烷-2-基)苯基甲基)丙酸甲酯
根据实施例1方法,但使用4-(叔丁基)-2-(2-苯基丙-2-基)苯酚(化合物24-1)和3-(4-羟基-3-(2-苯基丙烷-2-基)苯基)丙酸甲酯化合物(24-2)进行反应。得到化合物(24)。
化合物(24-1)或化合物(24-2)制法如下:根据实施例1方法,15g的4-叔丁基苯酚(或29.8g的3-(4-羟基-3-(2-苯基丙烷-2-基)苯基)丙酸甲酯)和15.4g的2-氯-2-苯基丙烷(CAS RN,515-40-2)、加入200mL的二氯甲烷,氮气搅拌下,加入加入无水14g的AlCl3搅拌过夜。TLC监控显示反应完成。反应混合物倾倒入200mL冰水中,搅拌,用CH2Cl2萃取3次。合并萃取相,依次用1%稀盐酸和盐水洗涤,无水硫酸钠干燥。蒸发仪上蒸干溶剂,得到的残余物使用柱层析纯化,得到化合物(24-1),MS(m/z)=268.2或化合物(24-2)。MS(m/z)=298.2。
实施例25
3-(3-(5-(叔丁基)-2-羟基苄基)-5-((十二烷基硫代)甲基)-4-羟基苯基)丙酸甲酯
根据实施例1方法,但以3-(3-(十二烷基硫代)-4-羟基苯基)丙酸甲酯,代替化合物(1),得到化合物(25)。MS(m/z)=570.4。
3-(3-(十二烷基硫代)-4-羟基苯基)丙酸甲酯制法:100g的4-羟基苯基-丙酸甲酯加入十二烷硫醇86g、多聚甲醛19g、二甲基甲酰胺150mL、哌啶3.6g,在氮气保护下加热回流过夜。过滤、水洗、抽滤后得到化合物(25.2)。
实施例26
3-(3-(叔丁基)-5-(3,5-二叔丁基-4-羟基苄基)-4-羟基苯基)丙酸甲酯
取25.4g的2,6-二叔丁基-4-氯甲基酚(CAS No 955-01-1,mp=40℃)和29g的3-(3-(叔丁基)-4-羟基苯基)丙酸甲酯(CAS No 36837-50-0,mp=60℃),溶于200mL干燥的CH2Cl2,氮气下室温下搅拌,加入无水14g的AlCl3搅拌。TLC监控反应,其间补充AlCl3。反应完成后,反应混合物倾倒入200mL冰水中,搅拌,用CH2Cl2萃取3次。合并萃取相,依次用1%稀盐酸和盐水洗涤,无水硫酸钠干燥。蒸发仪上蒸干溶剂,得到的残余物使用柱层析纯化,得到化合物(26)。MS(m/z)=454.3。
实施例27
3-(3-(叔丁基)-5-(3,5-二叔丁基-4-羟基苯甲酰基)-4-羟基苯基)丙酸甲酯
根据实施例26方法,但以3,5-二叔丁基-4-羟基苯甲酰氯,代替2,6-二叔丁基-4-氯甲基酚,得到化合物(27)。MS(m/z)=468.3。
实施例28
3-(3-叔丁基-5-((3,5-二叔丁基-4-羟基苯基)(羟基)甲基)-4-羟基苯基)丙酸甲酯
根据实施例3方法,但以化合物(27)代替化合物(2),得到化合物(28)。MS(m/z)=470.3。
实施例29
3-(3-(叔丁基)-5-(1-(3,5-二叔丁基-4-羟基苯基)乙基)-4-羟基苯基)丙酸甲酯
根据实施例1方法,但以乙醛代替聚甲醛,得到化合物(29)。MS(m/z)=468.3。
实施例30
3-(3-(叔丁基)-5-(3-(叔丁基)-4-羟基-5-甲基苄基)-4-羟基苯基)丙酸甲酯
根据实施例26方法,但以2-(氯甲基)-4-(叔丁基)-6-甲基苯酚,代替2,4-二叔丁基-6-氯甲基酚,得到化合物(30)。MS(m/z)=412.3。
实施例31
3-(3-(叔丁基)-5-(3,5-二叔丁基-4-羟基苄基)-4-羟基苯基)丙酸辛酯
根据实施例6方法,但以,但以化合物(26)代替化合物(1),得到化合物(31)。MS(m/z)=552.4。
实施例32
3-(3,5-二叔丁基-5-(3,5-二叔丁基-4-羟基苄基)-4-羟基苯基)丙酸十八烷基酯
根据实施例7方法,但以,但以化合物(26)代替化合物(1),得到化合物(32)。MS(m/z)=692.6。
实施例33
氧代双(乙烷-2,1-二基)双(3-(3-(叔丁基)-5-(3,5-二叔丁基-4-羟基苄基)-4-羟基苯基)丙酸酯)
将120g化合物(26),和13g二甘醇、0.5g三异丙醇铝(甲苯中)混合。将反应混合物搅拌并在氮气环境下85℃,升温,抽真空将生成的甲醇冷凝除去。监控反应,当反应完成,加入柠檬酸水溶液(50%),连续搅拌20分钟。然后,在75℃将水加入并搅拌20分钟。将有机相分离,然后用盐水洗涤两次,然后用硫酸钠干燥。接着甲苯和过量的辛醇从有机相在减压下蒸馏出,将残留物真空干燥。经层析分离,得到化合物(33)。MS(m/z)=950.6。
实施例34
(乙烷-1,2-二基双(氧基))双(乙烷-2,1-二基)双(3-(3-(叔丁基)-5-(3,5-二叔丁基-4-)羟基苄基)-4-羟基苯基)丙酸酯)
根据实施例33方法,但以三甘醇代替二甘醇,得到化合物(34)。MS(m/z)=994.7。
实施例35
硫代双(乙烷-2,1-二基)双(3-(3-(叔丁基)-5-(3,5-二叔丁基-4-羟基苄基)-4-羟基苯基)丙酸酯)
根据实施例33方法,但以2,2'-硫代二乙醇代替二甘醇,得到化合物(35)。MS(m/z)=966.6
实施例36
3,6,9,12,15,18,21,24-八氧代二十六烷-1,26-二基双(3-(3-(叔丁基)-5-(3,5-二叔丁基-4-)羟基苄基)-4-羟基苯基)丙酸酯)
根据实施例33方法,但以九甘醇代替二甘醇,经层析得到化合物(36)。
实施例37
N,N'-(丙烷-1,3-二基)双(3-(3-叔丁基-5-(3,5-二叔丁基-4-羟基苄基)-4-羟基苯基)丙酰胺)
根据实施例12方法,但以,但以化合物(26)代替化合物(1),得到化合物(37)。MS(m/z)=960.7。
实施例38
1,6-二基双(3-(3-叔丁基-5-(3,5-二叔丁基-4-羟基苄基)-4-羟基苯基)丙酸己酯)
根据实施例13方法,但以化合物(26)代替化合物(1),得到化合物(38)。MS(m/z)=962.7。
实施例39
双(乙烷-2,1-二基)双(3-(3-叔丁基-5-(3,5-二叔丁基-4-羟基苄基))-4-羟基苯基)丙酸(草酰二(氮杂-二基))酯
根据根据实施例14方法,但使用化合物(26)代替化合物(1)。得到化合物(39)。MS(m/z)=1020.6。
实施例40
(2,4,8,10-四氧杂螺[5.5]十一烷-3,9-二基)双(2-甲基丙烷-2,1-二基)双(3-(3-叔丁基)-5-(3,5-二-叔丁基-4-羟基苄基)-4-羟基苯基)丙酸酯)
根据实施例15方法,但以化合物(26)代替化合物(1)。得到化合物(40)。MS(m/z)=1148.8。
实施例41
N-3-(3-叔丁基-5-(3,5-二叔丁基-4-羟基苄基)-4-羟基苯基)-N'-(3-(3-叔丁基-5-(3,5-二叔丁基-4-羟基苄基)-4-羟基苯基)丙酰基)丙烷酰肼
根据实施例16方法,但以化合物(26)代替化合物(1)。得到化合物(41)。MS(m/z)=876.6。
实施例42
四(3-(3-叔丁基)-5-(3,5-二-叔丁基-2-羟基苄基)-4-羟基苯基)苯丙酸季戊四醇酯
根据实施例17方法,但使用化合物(26)代替化合物(1)。得到化合物(42)。MS(m/z)=1945.2。
实施例43
N,N”,N”'-(1,3,5-三嗪-2,4,6-三基)三(3-(3-(叔丁基)-5-(3,5-二叔丁基-4-羟基苄基)-4-羟基苯基)丙酰胺)
根据实施例18方法,但使用化合物(26)代替化合物(1)。得到化合物(43)。MS(m/z)=1392.9。
实施例44
(2,4,6-三氧代-1,3,5-三嗪-1,3,5-三基)三(乙烷-2,1-二基)三(3-(3-(叔丁基)-5-(3,5-二叔丁基-4-羟基苄基)-4-羟基苯基)丙酸酯)
根据实施例19方法,但使用化合物(26)代替化合物(1)。得到化合物(44)。MS(m/z)=1527.9。
实施例45
1,3,5-三基三(乙烷-2,1-二基)三(3-(3-(叔丁基)-5-((3,5-二叔丁基-4-羟基苄基)-4-羟基苯基)丙酸苯酯)
根据实施例20方法,但使用化合物(26)代替化合物(1)。1,3,5苯三甲醇(4464-18-0)代替2,4,6-三甲基苯-1,3,5-三基)三甲醇。得到化合物(45)。MS(m/z)1434.9。
实施例46
1,2,3-三(3-(3-(叔丁基)-5-(2,4-二叔丁基-4-羟基苄基)-4-羟基苯基)丙酸苯酯)丙烷
根据实施例22方法,但使用化合物(26)代替化合物(1)。得到化合物(45)。MS(m/z)=1358.9。
实施例47
3-(3-(3-(叔丁基)-4-羟基-5-(2-苯基丙烷-2-基)苄基)-4-羟基-5-(2-苯基丙烷-2-基)苯基甲基)丙酸甲酯
根据实施例24方法,但使用2-(叔丁基)-4-(氯甲基)-6-(2-苯基丙-2-基)苯酚(化合物47.1),代替化合物(24.1)。得到化合物(47)。MS(m/z)=578.3。
实施例48
己烷-1,6-二基双(3-(3-(3-(叔丁基)-4-羟基-5-(2-苯基丙烷-2-基)苄基)-4-羟基-5-(2-苯基丙-2-基)苯基)丙酸甲酯)
根据实施例13法,但使用化合物(47)代替化合物(1)。得到化合物(48)。MS(m/z)=1210.7。
实施例49
3-(3-(3,5-二叔丁基-4-羟基苄基)-5-((十二烷基硫代)甲基)-4-羟基苯基)丙酸甲酯
根据实施例25法,但使用2,6-二-叔丁基-4-(氯甲基)苯酚,代替化合物(25.1)。得到化合物(49)。MS(m/z)=612.4。
实施例50
丁烷-1,4-二基双(3-(3-(3,5-二叔丁基-4-羟基苄基)-5-((十二烷基硫代)甲基)-4-羟基苯基)丙酸酯)
根据实施例13方法,但使用代替化合物(49)代替化合物(1)。丁二醇代替己二醇。得到化合物(50)。MS(m/z)=1250.9。
实施例51
3-(3,5-二叔丁基-2-(3,5-二叔丁基-4-羟基苄基)-4-羟基苯基)丙酸甲酯
25.4g的3,5-二叔丁基-4-羟基苄基氯化物(CAS No 955-01-1,mp=40℃)和29.2g的(3,5-二叔丁基-4-羟基苯基)丙酸甲酯(CAS No 6386-38-5,mp=66℃),溶于200mL干燥的CH2Cl2,氮气下室温下搅拌,加入无水14g的AlCl3搅拌。TLC监控反应,其间补充AlCl3。反应完成后,反应混合物倾倒入200mL冰水中,搅拌,用CH2Cl2萃取3次。合并萃取相,依次用1%稀盐酸和盐水洗涤,无水硫酸钠干燥。蒸干溶剂,得到的残余物使用柱层析纯化,得到化合物(51)。MS(m/z)=510.4。
实施例52
3-(3,5-二叔丁基-2-(3,5-二叔丁基-4-羟基苯甲酰基)-4-羟基苯基)丙酸甲酯
根据实施例51方法,但以3,5-二叔丁基-4-羟基苯甲酰氯,代替3,5-二叔丁基-4-羟基苄基氯化物,得到化合物(2)。MS(m/z)=524.4。
实施例53
3-(3,5-二叔丁基-2-((3,5-二叔丁基-4-羟基苯基)(羟基)甲基)-4-羟基苯基)丙酸甲酯
根据实施例3的方法,但以化合物(52)代替化合物(2),得到化合物(53)。MS(m/z)=526.4。
实施例54
3-(3,5-二叔丁基-2-(氯(3,5-二叔丁基-4-羟基苯基)甲基)-4-羟基苯基)丙酸甲酯
将51克的化合物(53)溶于甲苯中,在冷凝分水器配置下,110℃加热回流。甲苯溶液中加入6克乙酸和1.5mL浓硫酸。监控反应,反应完成后。加入饱和的NaHCO3中和,再以二氯甲烷萃取。然后以饱和NaCl洗涤,无水MgSO4干燥。过滤后蒸干,通过柱层析,得到化合物(54)。MS(m/z)=568.4。
实施例55
3-(5-(叔丁基)-2-(1-(3,5-二叔丁基-2-羟基苯基)-2-苯乙基)-4-羟基苯基)丙酸甲酯
根据实施例4方法,但以苯乙醛代替乙醛,化合物2,6-二-叔丁基酚代替化合物(4.1),化合物(51.2)代替化合物(1.2)。经层析法分离,得到化合物(55)。MS(m/z)=600.4。
实施例56
3-(3,5-二叔丁基-2-(3,5-二叔丁基-4-羟基苄基)-4-羟基苯基)丙酸辛酯
根据实施例6的方法,但以化合物(51)代替化合物(1),得到化合物(56)。MS(m/z)=608.5。
实施例57
(乙烷-1,2-二基双(氧))双(乙烷-2,1-二基)双(3-(5-(叔丁基)-2-(3,5-二叔丁基-4-)羟基苄基)-4-羟基苯基)丙酸酯)
根据实施例10的方法,但以化合物(51)代替化合物(1),得到化合物(57)。MS(m/z)=1106.8。
实施例58
3-(5-(叔丁基)-2-(3,5-二叔丁基-4-羟基苄基)-4-羟基苯基)-N'-(3-(5-(叔丁基)-2--(3,5-二-叔丁基-4-羟基苄基)-4-羟基苯基)丙酰基)丙烷酰肼
根据实施例16的方法,但以化合物(51)代替化合物(1),得到化合物(58)。MS(m/z)=988.7。
实施例59
2-(乙酰氧基亚氨基)-1-(4-((4-(3-氧代-3-苯基丙-1-烯-1-基)苯基)硫基)苯基)己-1-酮
根据实施例17的方法,但以化合物(51)代替化合物(1),得到化合物(59)。MS(m/z)=2155.5。
实施例60:抗氧化剂在聚氨酯的析出测试
聚醚多元醇是聚氨酯原料。混合50重量分聚醚多元醇(triol,分子量3000)、2.0重量分水、0.1重量分三乙烯二胺、1.0重量分硅油后。加入包括0.2重量分辛酸亚锡、0.15重量分的实施例化合物或对照组化合物、50重量分甲苯二异氰酸酯、50重量分聚醚多元醇(triol,分子量3000),的混合物。二者混合后,倒入盒中进行发泡反应。室温静置1小时,在烘箱中熟化。反应完成后,将掺有或未掺有抗氧化剂的聚氨酯切下1克样品,放到加盖的玻璃罐中进行抗萃取或抗老化分析。加入100ml溶剂进行萃取,并对萃取液进行分析。HPLC检测各种化合物的萃取量。以对照组所萃取出的量为100%。萃取出的量愈少,代表愈不容易析出。基本上,受测试化合物所具有抗老化或抗黄变能力,和受阻酚单元数正相关。抗萃取测试结果显示于表4。以对照组被萃取为100%,换算实例化合物被萃取的相对比例。实例化合物被萃取出百分比=(100÷对照组被萃取出量a)×(实例化合物萃取出量b)×%。实例化合物的总体抗氧化效率,正比于萃取后在聚氨酯的残余量,且正比于(受阻酚单元数/分子量)。例如,化合物10和Eunox 1035的(受阻酚单元/分子量)的比值为(4/966):(2/642)=1.33,只要残余量比值大于1,即可推定具有进步性。表4实例化合物被萃取出的百分比都小于75%,即残余量比值都大于1。
表4.抗氧化剂的析出测试
表4.续
对照品全都来自市面商品或专利,Eunox是申请人商标名,41028-42-6(CAS no)来自专利(JP56052073),结构式如下:
以上已以较佳实施例公开了本发明,然其并非用以限制本发明,凡采用等同替换或者等效变换方式所获得的技术方案,均落在本发明的保护范围之内。
Claims (8)
2.根据权利要求1所述的化合物,其特征在于,R7选自一键、氢、未取代或经取代的碳或碳链、未取代或经取代的氧或硫或氮或金属原子、未取代或经取代的经氧或硫或氮所中断的碳链、未取代或经取代的5-7元碳环或含氧或硫或氮的5-7元杂环。
3.根据权利要求1所述的化合物,其特征在于,R1、R2各自独立地选自含C1-C5的烷基、苯基、苄基、枯基;R3、R4各自独立地选自氢、羟基、C1-C5的烷基、酰基、C1-C5烷基胺基、C1-C5烷氧基;R5、R6各自独立地选自氢、羟基、苯基、C1-C5的烷基、酰基;R7选自H、一键、(C)a(CH)b(CH2)c(CH3)d,其中a、b、c、d=0~18,a、b、c、d不同时为0、(CH2CH2O)tH、(CH2CH2O)tOCH3、(CH)q-2(CH2)0~12(CH3)1-3、S、SH、O、OH、N、NH、NHR8、P、Ca、Mg、Zn、Na、K、-(CHR8)1~18-、-(CH)q-2(CH2)1~18-、-(C=O)1-4-、-(CHR8)u(C=O)1-4(CHR8)u-、-(CHR8)uS1-4(CHR8)u-、-(CHR8)uO1-4(CHR8)u-、-(CH2CH2O)tCH2CH2-、三嗪类、三聚氰胺类、未取代或经取代的苯基或芐基;q≧a+b+c+d;t=1-20;u=1-10。
5.根据权利要求1所述的化合物,其特征在于,m=1;n=2;q=1-4。
8.一种低迁移受阻酚抗氧化组合物,其包括至少一种权利要求1-6任一项所述的式(II)化合物或其盐。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202211316611.8A CN115819238A (zh) | 2020-03-26 | 2020-03-26 | 一种低迁移受阻酚抗氧化合物、制备方法及组合物 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202211316611.8A CN115819238A (zh) | 2020-03-26 | 2020-03-26 | 一种低迁移受阻酚抗氧化合物、制备方法及组合物 |
CN202010222099.5A CN113443991A (zh) | 2020-03-26 | 2020-03-26 | 一种低迁移受阻酚抗氧化合物、制备方法及组合物 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202010222099.5A Division CN113443991A (zh) | 2020-03-26 | 2020-03-26 | 一种低迁移受阻酚抗氧化合物、制备方法及组合物 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN115819238A true CN115819238A (zh) | 2023-03-21 |
Family
ID=77807082
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202211316611.8A Pending CN115819238A (zh) | 2020-03-26 | 2020-03-26 | 一种低迁移受阻酚抗氧化合物、制备方法及组合物 |
CN202010222099.5A Pending CN113443991A (zh) | 2020-03-26 | 2020-03-26 | 一种低迁移受阻酚抗氧化合物、制备方法及组合物 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202010222099.5A Pending CN113443991A (zh) | 2020-03-26 | 2020-03-26 | 一种低迁移受阻酚抗氧化合物、制备方法及组合物 |
Country Status (6)
Country | Link |
---|---|
US (1) | US20230312457A1 (zh) |
JP (1) | JP2023520386A (zh) |
KR (1) | KR20220158070A (zh) |
CN (2) | CN115819238A (zh) |
TW (1) | TW202208327A (zh) |
WO (1) | WO2021190569A1 (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114213291B (zh) * | 2021-12-31 | 2022-08-09 | 江苏极易新材料有限公司 | 硫代二乙撑双[3-(3,5-二叔丁基-4-羟基苯基)丙酸酯]的合成方法 |
CN115651418A (zh) * | 2022-11-09 | 2023-01-31 | 深圳新红进科技有限公司 | 一种道路沥青抗老化剂及其制备方法 |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL161484C (nl) * | 1969-07-10 | 1980-02-15 | Hoechst Ag | Werkwijze voor het bereiden van gestabiliseerde poly- alkenen. |
BE757795A (fr) * | 1969-10-23 | 1971-04-21 | Hoechst Ag | Procede de preparation de produits de condensation de phenols et de polyesters de l'acide acetylacetique |
US3960928A (en) * | 1969-10-23 | 1976-06-01 | Hoechst Aktiengesellschaft | Process for the manufacture of condensation products from phenols and polyacetoacetic acid esters |
JPS5027488B2 (zh) * | 1971-12-17 | 1975-09-08 | ||
FR2259809B1 (zh) * | 1974-02-01 | 1978-08-11 | Nobel Hoechst Chimie | |
DE2544014A1 (de) * | 1975-10-02 | 1977-04-14 | Hoechst Ag | Polare phenolische antioxidantien zur stabilisierung von kunststoffen |
DE2717087A1 (de) * | 1976-04-28 | 1977-11-10 | Ciba Geigy Ag | Neue stabilisatoren |
US4197236A (en) * | 1976-04-28 | 1980-04-08 | Ciba-Geigy Corporation | Piperidine stabilizers |
US4645853A (en) * | 1985-08-30 | 1987-02-24 | Ici Americas Inc. | Hindered phenolic oxamide compounds and stabilized compositions |
JPS6429341A (en) * | 1987-07-23 | 1989-01-31 | Yoshitomi Pharmaceutical | Bis(4-hydroxyphenylpropionic acid ester) compound and use thereof |
JP2007279413A (ja) * | 2006-04-07 | 2007-10-25 | Konica Minolta Medical & Graphic Inc | 熱現像感光材料 |
JP2008231089A (ja) * | 2007-02-19 | 2008-10-02 | Konica Minolta Medical & Graphic Inc | ビスフェノール化合物 |
JP5743327B2 (ja) * | 2008-12-12 | 2015-07-01 | インジェニア・ポリマーズ・インコーポレイテッドIngenia Polymers, Inc. | ポリマー用の圧縮ペレット化添加剤ブレンド |
CN104250216B (zh) * | 2013-06-28 | 2016-07-13 | 中国石油天然气股份有限公司 | 一种抗静电抗氧化双功能化合物及其合成方法 |
CN104292141B (zh) * | 2014-08-18 | 2016-03-02 | 华南理工大学 | 含硫醚和氨基甲酸酯基团的大分子受阻酚抗氧剂及其制备方法与应用 |
WO2016052170A1 (ja) * | 2014-09-30 | 2016-04-07 | 富士フイルム株式会社 | 有機電子デバイス、有機薄膜トランジスタ、電子ペーパー、ディスプレイデバイス |
CN108164439A (zh) * | 2018-02-26 | 2018-06-15 | 上海朗亿功能材料有限公司 | 一种具有抗氧化功能的碳化二亚胺类化合物及其制备方法 |
CN110862317B (zh) * | 2019-12-02 | 2022-04-22 | 山东省临沂市三丰化工有限公司 | 一种受阻酚类抗氧剂及其制备方法 |
-
2020
- 2020-03-26 CN CN202211316611.8A patent/CN115819238A/zh active Pending
- 2020-03-26 CN CN202010222099.5A patent/CN113443991A/zh active Pending
-
2021
- 2021-03-23 TW TW110110333A patent/TW202208327A/zh unknown
- 2021-03-24 KR KR1020227037289A patent/KR20220158070A/ko unknown
- 2021-03-24 WO PCT/CN2021/082762 patent/WO2021190569A1/zh active Application Filing
- 2021-03-24 US US17/914,559 patent/US20230312457A1/en active Pending
- 2021-03-24 JP JP2022558562A patent/JP2023520386A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
WO2021190569A1 (zh) | 2021-09-30 |
TW202208327A (zh) | 2022-03-01 |
US20230312457A1 (en) | 2023-10-05 |
KR20220158070A (ko) | 2022-11-29 |
JP2023520386A (ja) | 2023-05-17 |
CN113443991A (zh) | 2021-09-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN115819238A (zh) | 一种低迁移受阻酚抗氧化合物、制备方法及组合物 | |
US5427701A (en) | Substituted phenols as stabilizers | |
Ohkatsu et al. | Antioxidant and photo-antioxidant activities of chalcone derivatives | |
WO2016066057A1 (zh) | 一种3-芳基苯并呋喃酮化合物及其构成的组合物 | |
CN109096102A (zh) | 一种受阻酚类抗氧剂的合成技术 | |
JP4719916B2 (ja) | ヒドロキシスチレン誘導体及びアセトキシスチレン誘導体の製造方法 | |
US3579591A (en) | 4,4'-bis-(hydroxyarloxy)-phenylsulfone | |
JPS5935906B2 (ja) | 2,4,6−トリ(3,5−ジアルキル−4−ヒドロキシベンジル)フエノ−ルの製造方法 | |
CN111689853B (zh) | 一种层状双酚丙烯酸酯抗氧剂及其制备方法 | |
CA1172645A (en) | Chroman derivatives | |
US4254020A (en) | Synergistic antioxidant mixtures | |
CN115819842B (zh) | 一种聚合物用的含受阻酚的耐着色抗氧剂组合物 | |
US6365781B2 (en) | Process for the preparation of mercaptomethylphenois | |
CN112010800B (zh) | 一种含受阻酚的受阻胺光稳定剂及其制备方法和应用 | |
US4820756A (en) | Thioether substituted phenols and their use as stabilizers | |
US20050049307A1 (en) | Organic thiol metal-free stabilizers and plasticizers for halogen-containing polymers | |
US6927247B2 (en) | Organic thiol metal-free stabilizers and plasticizers for halogen-containing polymers | |
JPH0348177B2 (zh) | ||
US3491102A (en) | 2-hydroxy - 3,5 - dihydrocarbylbenzyl 3-hydrocarbyl - 4 - hydroxy-5-(dialkylaminomethyl) phenyl sulfide | |
US4448915A (en) | Acetylene carbamide derivatives, processes for their production, and antioxidants for organic substances which comprise such derivatives as active ingredients | |
GB2264708A (en) | Carboxylic acid esters of hydroxyphenylalkanols as stabilisers | |
EP1116714B1 (en) | Improved process for the preparation of mercaptomethylphenols | |
Yamato et al. | Synthesis and ion selectivity of macrocyclic metacyclophanes analogous to spherand-type calixarenes | |
EP0426144B1 (en) | Organic sulfide antioxidants | |
US3952063A (en) | Process for the preparation of an organomercaptophenol from sulfur, a phenol, and an activated olefin or an epoxy compound |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination |