CZ289139B6 - Benzofuran-2-on, stabilizovaná kompozice tento benzofuran-2-on obsahující, pouľití tohoto benzofuran-2-onu jako stabilizátoru, způsob stabilizace syntetického polymeru a způsob přípravy uvedeného benzofuran-2-onu - Google Patents

Info

Publication number

CZ289139B6

CZ289139B6 CZ19942261A CZ226194A CZ289139B6 CZ 289139 B6 CZ289139 B6 CZ 289139B6 CZ 19942261 A CZ19942261 A CZ 19942261A CZ 226194 A CZ226194 A CZ 226194A CZ 289139 B6 CZ289139 B6 CZ 289139B6

Authority

CZ

Czechia

Prior art keywords

formula

benzofuran

group

tert

hydrogen

Prior art date

1993-09-17

Links

• Espacenet
• Global Dossier
• Discuss

• ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 title claims abstract description 40
• 239000000203 mixture Substances 0.000 title claims abstract description 39
• 229920001059 synthetic polymer Polymers 0.000 title claims abstract description 22
• 239000003381 stabilizer Substances 0.000 title claims abstract description 20
• 238000000034 method Methods 0.000 title claims abstract description 18
• 238000004519 manufacturing process Methods 0.000 title abstract description 5
• 230000006641 stabilisation Effects 0.000 title abstract 2
• 238000011105 stabilization Methods 0.000 title abstract 2
• 230000015556 catabolic process Effects 0.000 claims abstract description 13
• 238000006731 degradation reaction Methods 0.000 claims abstract description 13
• 230000003647 oxidation Effects 0.000 claims abstract description 9
• 238000007254 oxidation reaction Methods 0.000 claims abstract description 9
• -1 chloro, hydroxy Chemical group 0.000 claims description 82
• 150000001875 compounds Chemical class 0.000 claims description 64
• HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 36
• 125000004432 carbon atom Chemical group C* 0.000 claims description 32
• 229910052739 hydrogen Inorganic materials 0.000 claims description 24
• 239000001257 hydrogen Substances 0.000 claims description 23
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
• 239000002253 acid Substances 0.000 claims description 18
• 125000000217 alkyl group Chemical group 0.000 claims description 18
• 229910052801 chlorine Inorganic materials 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 238000002360 preparation method Methods 0.000 claims description 12
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
• 239000000654 additive Substances 0.000 claims description 11
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
• 150000002148 esters Chemical class 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 9
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
• 239000000460 chlorine Substances 0.000 claims description 8
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
• 230000000087 stabilizing effect Effects 0.000 claims description 8
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
• 229910052794 bromium Chemical group 0.000 claims description 6
• 125000001589 carboacyl group Chemical group 0.000 claims description 6
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
• 150000008064 anhydrides Chemical class 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 150000004820 halides Chemical class 0.000 claims description 5
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 239000012948 isocyanate Substances 0.000 claims description 5
• 150000002513 isocyanates Chemical class 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
• 125000001153 fluoro group Chemical group F* 0.000 claims description 4
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
• 239000007864 aqueous solution Substances 0.000 claims description 3
• 239000002530 phenolic antioxidant Substances 0.000 claims description 3
• OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 3
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
• 125000002947 alkylene group Chemical group 0.000 claims description 2
• 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 2
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
• 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims description 2
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• 229910052731 fluorine Inorganic materials 0.000 claims description 2
• 229910052740 iodine Chemical group 0.000 claims description 2
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
• 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 2
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
• 150000003015 phosphoric acid halides Chemical class 0.000 claims description 2
• 239000003223 protective agent Substances 0.000 claims description 2
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 9
• 230000000996 additive effect Effects 0.000 claims 1
• 239000011737 fluorine Substances 0.000 claims 1
• QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical group ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims 1
• 239000004615 ingredient Substances 0.000 claims 1
• 239000011630 iodine Chemical group 0.000 claims 1
• GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 1
• 230000001747 exhibiting effect Effects 0.000 abstract 1
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• 238000006243 chemical reaction Methods 0.000 description 28
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
• 229920000642 polymer Polymers 0.000 description 18
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• 239000003054 catalyst Substances 0.000 description 15
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 14
• 239000005977 Ethylene Substances 0.000 description 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
• 239000002904 solvent Substances 0.000 description 12
• 239000004952 Polyamide Substances 0.000 description 11
• 229920002647 polyamide Polymers 0.000 description 11
• 229920005989 resin Polymers 0.000 description 11
• 239000011347 resin Substances 0.000 description 11
• 239000005062 Polybutadiene Substances 0.000 description 10
• 239000004743 Polypropylene Substances 0.000 description 10
• 229920002857 polybutadiene Polymers 0.000 description 10
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• 229920001684 low density polyethylene Polymers 0.000 description 9
• 239000004702 low-density polyethylene Substances 0.000 description 9
• 150000004760 silicates Chemical class 0.000 description 9
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
• 229910052751 metal Inorganic materials 0.000 description 8
• 239000002184 metal Substances 0.000 description 8
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
• 238000005160 1H NMR spectroscopy Methods 0.000 description 7
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
• 150000001412 amines Chemical class 0.000 description 7
• HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 7
• 150000002170 ethers Chemical class 0.000 description 7
• AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 7
• 229920000098 polyolefin Polymers 0.000 description 7
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• 239000011541 reaction mixture Substances 0.000 description 7
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• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
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• 239000004698 Polyethylene Substances 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
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• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 239000007983 Tris buffer Substances 0.000 description 6
• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 6
• 229910000323 aluminium silicate Inorganic materials 0.000 description 6
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
• 239000004417 polycarbonate Substances 0.000 description 6
• 229920000573 polyethylene Polymers 0.000 description 6
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• 239000004800 polyvinyl chloride Substances 0.000 description 6
• 239000000047 product Substances 0.000 description 6
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• KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 5
• OFQJSKKMBIPWPB-UHFFFAOYSA-N 7-tert-butyl-3-hydroxy-5-methyl-3h-1-benzofuran-2-one Chemical compound CC(C)(C)C1=CC(C)=CC2=C1OC(=O)C2O OFQJSKKMBIPWPB-UHFFFAOYSA-N 0.000 description 5
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• KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 5
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• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
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