NL9300801A

NL9300801A - 3-(acyloxyfenyl)benzofuran-2-on als stabilisatoren.

3-(acyloxyfenyl)benzofuran-2-on als stabilisatoren. Download PDF

Info

Publication number: NL9300801A
Authority: NL; Netherlands
Prior art keywords: hydrogen; alkyl; tert; butyl; alkanoyl
Prior art date: 1992-05-22

Application number

NL9300801A

Other languages

English (en)

Dutch (nl)

Original Assignee

Ciba Geigy

Priority date

1992-05-22

Filing date

1993-05-10

Publication date

1993-12-16

1993-05-10 Application filed by Ciba Geigy filed Critical Ciba Geigy

1993-12-16 Publication of NL9300801A publication Critical patent/NL9300801A/nl

Links

239000003381 stabilizer Substances 0.000 title claims description 20
ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 title description 6
239000001257 hydrogen Substances 0.000 claims description 86
229910052739 hydrogen Inorganic materials 0.000 claims description 86
150000001875 compounds Chemical class 0.000 claims description 64
239000000203 mixture Substances 0.000 claims description 52
150000002431 hydrogen Chemical class 0.000 claims description 47
125000000217 alkyl group Chemical group 0.000 claims description 37
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
125000001589 carboacyl group Chemical group 0.000 claims description 28
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 15
229910052717 sulfur Inorganic materials 0.000 claims description 15
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
125000002947 alkylene group Chemical group 0.000 claims description 14
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
239000001301 oxygen Substances 0.000 claims description 14
229910052760 oxygen Inorganic materials 0.000 claims description 14
239000011593 sulfur Substances 0.000 claims description 14
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
239000011368 organic material Substances 0.000 claims description 11
238000000034 method Methods 0.000 claims description 10
230000015556 catabolic process Effects 0.000 claims description 9
238000006731 degradation reaction Methods 0.000 claims description 8
125000001118 alkylidene group Chemical group 0.000 claims description 7
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 7
230000001590 oxidative effect Effects 0.000 claims description 7
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 7
125000004450 alkenylene group Chemical group 0.000 claims description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 5
XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 5
125000002993 cycloalkylene group Chemical group 0.000 claims description 4
125000004956 cyclohexylene group Chemical group 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
230000000087 stabilizing effect Effects 0.000 claims description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 3
GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 2
229920001059 synthetic polymer Polymers 0.000 claims description 2
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 1
229910021554 Chromium(II) chloride Inorganic materials 0.000 claims 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
-1 1-methypentyl Chemical group 0.000 description 154
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
229920000642 polymer Polymers 0.000 description 23
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 22
229920001228 polyisocyanate Polymers 0.000 description 22
239000005056 polyisocyanate Substances 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
229910052757 nitrogen Inorganic materials 0.000 description 16
229920000570 polyether Polymers 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
238000002360 preparation method Methods 0.000 description 14
239000006260 foam Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
239000004743 Polypropylene Substances 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000002253 acid Substances 0.000 description 12
239000003054 catalyst Substances 0.000 description 12
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
150000002148 esters Chemical class 0.000 description 12
229920002857 polybutadiene Polymers 0.000 description 12
239000004814 polyurethane Substances 0.000 description 12
239000000654 additive Substances 0.000 description 11
229910052751 metal Inorganic materials 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
239000004952 Polyamide Substances 0.000 description 10
239000004721 Polyphenylene oxide Substances 0.000 description 10
125000004432 carbon atom Chemical group C* 0.000 description 10
239000002184 metal Substances 0.000 description 10
229920002647 polyamide Polymers 0.000 description 10
229920002635 polyurethane Polymers 0.000 description 10
239000000047 product Substances 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
230000006641 stabilisation Effects 0.000 description 10
238000011105 stabilization Methods 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
229920001684 low density polyethylene Polymers 0.000 description 9
239000004702 low-density polyethylene Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
239000005062 Polybutadiene Substances 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
229920000098 polyolefin Polymers 0.000 description 8
229920001155 polypropylene Polymers 0.000 description 8
239000004698 Polyethylene Substances 0.000 description 7
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
239000000463 material Substances 0.000 description 7
229920000573 polyethylene Polymers 0.000 description 7
239000002904 solvent Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
238000005187 foaming Methods 0.000 description 6
150000002989 phenols Chemical class 0.000 description 6
239000004417 polycarbonate Substances 0.000 description 6
229920000728 polyester Polymers 0.000 description 6
238000006116 polymerization reaction Methods 0.000 description 6
229920006324 polyoxymethylene Polymers 0.000 description 6
239000004800 polyvinyl chloride Substances 0.000 description 6
229920000915 polyvinyl chloride Polymers 0.000 description 6
229920002943 EPDM rubber Polymers 0.000 description 5
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
239000007859 condensation product Substances 0.000 description 5
150000001993 dienes Chemical class 0.000 description 5
ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 5
238000001035 drying Methods 0.000 description 5
229920001903 high density polyethylene Polymers 0.000 description 5
239000004700 high-density polyethylene Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
229920005862 polyol Polymers 0.000 description 5
150000003077 polyols Chemical class 0.000 description 5
235000013772 propylene glycol Nutrition 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
239000000243 solution Substances 0.000 description 5
150000005846 sugar alcohols Polymers 0.000 description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
229920002554 vinyl polymer 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
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
ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
229920000877 Melamine resin Polymers 0.000 description 4
150000001252 acrylic acid derivatives Chemical class 0.000 description 4
125000004423 acyloxy group Chemical group 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
239000003513 alkali Substances 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
235000014113 dietary fatty acids Nutrition 0.000 description 4
229920001971 elastomer Polymers 0.000 description 4
239000005038 ethylene vinyl acetate Substances 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
150000004665 fatty acids Chemical class 0.000 description 4
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 4
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
230000006698 induction Effects 0.000 description 4
238000004898 kneading Methods 0.000 description 4
229940098779 methanesulfonic acid Drugs 0.000 description 4
150000002815 nickel Chemical class 0.000 description 4
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 4
229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 4
229920000647 polyepoxide Polymers 0.000 description 4
229920006380 polyphenylene oxide Polymers 0.000 description 4
238000012545 processing Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
229920001169 thermoplastic Polymers 0.000 description 4
YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
238000004383 yellowing Methods 0.000 description 4
KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
YHXHKYRQLYQUIH-UHFFFAOYSA-N 4-hydroxymandelic acid Chemical class OC(=O)C(O)C1=CC=C(O)C=C1 YHXHKYRQLYQUIH-UHFFFAOYSA-N 0.000 description 3
JAJNCYNAFJZBCW-UHFFFAOYSA-N 5,7-ditert-butyl-3-(4-hydroxy-3,5-dimethylphenyl)-3h-1-benzofuran-2-one Chemical compound CC1=C(O)C(C)=CC(C2C3=C(C(=CC(=C3)C(C)(C)C)C(C)(C)C)OC2=O)=C1 JAJNCYNAFJZBCW-UHFFFAOYSA-N 0.000 description 3
CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
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ZSFWKZUHCKWKGK-UHFFFAOYSA-N [4-(5,7-ditert-butyl-2-oxo-3h-1-benzofuran-3-yl)-2,6-dimethylphenyl] 2,2-dimethylpropanoate Chemical compound CC1=C(OC(=O)C(C)(C)C)C(C)=CC(C2C3=C(C(=CC(=C3)C(C)(C)C)C(C)(C)C)OC2=O)=C1 ZSFWKZUHCKWKGK-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
239000002585 base Substances 0.000 description 3
239000011575 calcium Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
150000001991 dicarboxylic acids Chemical class 0.000 description 3
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150000002513 isocyanates Chemical class 0.000 description 3
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239000011777 magnesium Substances 0.000 description 3
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
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235000021317 phosphate Nutrition 0.000 description 3
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YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
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239000005977 Ethylene Substances 0.000 description 2
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PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
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