CZ290111B6 - Kompozice pro stabilizaci syntetických polymerů, 3-(alkoxyfenyl)benzofuran-2-on, jeho pouľití pro stabilizaci syntetických polymerů a způsob stabilizace syntetických polymerů - Google Patents

Info

Publication number

CZ290111B6

CZ290111B6 CZ1993919A CZ91993A CZ290111B6 CZ 290111 B6 CZ290111 B6 CZ 290111B6 CZ 1993919 A CZ1993919 A CZ 1993919A CZ 91993 A CZ91993 A CZ 91993A CZ 290111 B6 CZ290111 B6 CZ 290111B6

Authority

CZ

Czechia

Prior art keywords

carbon atoms

group

alkyl

hydrogen

phenyl

Prior art date

1992-05-22

Links

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• 239000000203 mixture Substances 0.000 title claims abstract description 60
• 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 21
• 229920001059 synthetic polymer Polymers 0.000 title claims abstract description 20
• 238000000034 method Methods 0.000 title claims abstract description 15
• 230000006641 stabilisation Effects 0.000 title abstract description 15
• 238000011105 stabilization Methods 0.000 title abstract description 15
• 125000004432 carbon atom Chemical group C* 0.000 claims description 170
• -1 pivaloyloxy Chemical group 0.000 claims description 136
• 125000000217 alkyl group Chemical group 0.000 claims description 92
• 229910052739 hydrogen Inorganic materials 0.000 claims description 67
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
• 150000001875 compounds Chemical class 0.000 claims description 65
• 239000001257 hydrogen Substances 0.000 claims description 56
• 150000002431 hydrogen Chemical class 0.000 claims description 37
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
• 229910052799 carbon Inorganic materials 0.000 claims description 25
• 125000003545 alkoxy group Chemical group 0.000 claims description 23
• 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 21
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
• 229910052717 sulfur Inorganic materials 0.000 claims description 17
• 125000004423 acyloxy group Chemical group 0.000 claims description 16
• 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 16
• 229910052751 metal Inorganic materials 0.000 claims description 16
• 239000002184 metal Substances 0.000 claims description 16
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 16
• 230000000087 stabilizing effect Effects 0.000 claims description 15
• 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 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 239000001301 oxygen Substances 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 12
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 12
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
• 125000000304 alkynyl group Chemical group 0.000 claims description 11
• 239000011593 sulfur Substances 0.000 claims description 11
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
• 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 9
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
• OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 8
• 230000015556 catabolic process Effects 0.000 claims description 7
• 150000001768 cations Chemical class 0.000 claims description 7
• 238000006731 degradation reaction Methods 0.000 claims description 7
• XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 7
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 7
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 230000001590 oxidative effect Effects 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• 125000004434 sulfur atom Chemical group 0.000 claims description 6
• 125000001424 substituent group Chemical group 0.000 claims description 2
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 33
• 229920001577 copolymer Polymers 0.000 description 31
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
• 229920000642 polymer Polymers 0.000 description 24
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 229920001228 polyisocyanate Polymers 0.000 description 21
• 239000005056 polyisocyanate Substances 0.000 description 21
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
• 239000000047 product Substances 0.000 description 17
• 239000003054 catalyst Substances 0.000 description 16
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• 239000003381 stabilizer Substances 0.000 description 15
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 14
• 239000004814 polyurethane Substances 0.000 description 14
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
• 239000002253 acid Substances 0.000 description 13
• 238000002844 melting Methods 0.000 description 13
• 230000008018 melting Effects 0.000 description 13
• 239000000126 substance Substances 0.000 description 13
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
• 239000004743 Polypropylene Substances 0.000 description 12
• 229920002635 polyurethane Polymers 0.000 description 12
• 239000011541 reaction mixture Substances 0.000 description 12
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• 229920002647 polyamide Polymers 0.000 description 11
• 229920000570 polyether Polymers 0.000 description 11
• 150000002148 esters Chemical class 0.000 description 10
• 229910052757 nitrogen Inorganic materials 0.000 description 10
• 229920002857 polybutadiene Polymers 0.000 description 10
• 239000000243 solution Substances 0.000 description 10
• 150000001412 amines Chemical class 0.000 description 9
• 150000001721 carbon Chemical group 0.000 description 9
• 229920001684 low density polyethylene Polymers 0.000 description 9
• 239000004702 low-density polyethylene Substances 0.000 description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
• 239000000654 additive Substances 0.000 description 8
• 238000004519 manufacturing process Methods 0.000 description 8
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
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• 239000006260 foam Substances 0.000 description 7
• 239000003921 oil Substances 0.000 description 7
• 229920000573 polyethylene Polymers 0.000 description 7
• 229920006324 polyoxymethylene Polymers 0.000 description 7
• 229920001155 polypropylene Polymers 0.000 description 7
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 6
• 238000006243 chemical reaction Methods 0.000 description 6
• 230000006698 induction Effects 0.000 description 6
• 229920000092 linear low density polyethylene Polymers 0.000 description 6
• 239000004707 linear low-density polyethylene Substances 0.000 description 6
• 239000000463 material Substances 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• 235000019198 oils Nutrition 0.000 description 6
• 239000004417 polycarbonate Substances 0.000 description 6
• 229920000728 polyester Polymers 0.000 description 6
• 239000004800 polyvinyl chloride Substances 0.000 description 6
• 229920000915 polyvinyl chloride Polymers 0.000 description 6
• 229920002554 vinyl polymer Polymers 0.000 description 6
• 239000004721 Polyphenylene oxide Substances 0.000 description 5
• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
• 229910052783 alkali metal Inorganic materials 0.000 description 5
• 125000003118 aryl group Chemical group 0.000 description 5
• 239000007859 condensation product Substances 0.000 description 5
• 229920001971 elastomer Polymers 0.000 description 5
• 150000004665 fatty acids Chemical group 0.000 description 5
• 238000005187 foaming Methods 0.000 description 5
• 238000004898 kneading Methods 0.000 description 5
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• 150000002989 phenols Chemical class 0.000 description 5
• 229920005862 polyol Polymers 0.000 description 5
• 238000002360 preparation method Methods 0.000 description 5
• 150000005846 sugar alcohols Polymers 0.000 description 5
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
• ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
• VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
• KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 4
• 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 4
• KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 4
• ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
• CXUYVOHLQSZWCW-UHFFFAOYSA-N 5,7-ditert-butyl-3-(4-ethoxyphenyl)-3h-1-benzofuran-2-one Chemical compound C1=CC(OCC)=CC=C1C1C(C=C(C=C2C(C)(C)C)C(C)(C)C)=C2OC1=O CXUYVOHLQSZWCW-UHFFFAOYSA-N 0.000 description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
• 229920002943 EPDM rubber Polymers 0.000 description 4
• 229920000877 Melamine resin Polymers 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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• 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
• TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
• 235000010290 biphenyl Nutrition 0.000 description 4
• 239000004305 biphenyl Substances 0.000 description 4
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• 239000003795 chemical substances by application Substances 0.000 description 4
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• 239000000194 fatty acid Substances 0.000 description 4
• 229930195729 fatty acid Natural products 0.000 description 4
• HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 4
• 238000010438 heat treatment Methods 0.000 description 4
• XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
• SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
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• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
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• 150000003839 salts Chemical class 0.000 description 4
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• 239000002904 solvent Substances 0.000 description 4
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• ZEBMSMUPGIOANU-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid Chemical compound CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O ZEBMSMUPGIOANU-UHFFFAOYSA-N 0.000 description 3
• 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 3
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