BE1011643A3 - Composition stabilisee, melange de stabilisants, et procede pour stabiliser une matiere organique. - Google Patents
Composition stabilisee, melange de stabilisants, et procede pour stabiliser une matiere organique. Download PDFInfo
- Publication number
- BE1011643A3 BE1011643A3 BE9800126A BE9800126A BE1011643A3 BE 1011643 A3 BE1011643 A3 BE 1011643A3 BE 9800126 A BE9800126 A BE 9800126A BE 9800126 A BE9800126 A BE 9800126A BE 1011643 A3 BE1011643 A3 BE 1011643A3
- Authority
- BE
- Belgium
- Prior art keywords
- group
- alkyl
- hydrogen
- substituted
- tert
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 141
- 239000003381 stabilizer Substances 0.000 title claims abstract description 57
- 238000000034 method Methods 0.000 title claims description 11
- 230000000087 stabilizing effect Effects 0.000 title claims description 8
- 239000005416 organic matter Substances 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 112
- 229920000098 polyolefin Polymers 0.000 claims abstract description 36
- 239000011368 organic material Substances 0.000 claims abstract description 27
- 150000001412 amines Chemical class 0.000 claims abstract description 23
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 230000015556 catabolic process Effects 0.000 claims abstract description 19
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 19
- 238000006731 degradation reaction Methods 0.000 claims abstract description 18
- 230000003647 oxidation Effects 0.000 claims abstract description 18
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims abstract description 17
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims abstract description 14
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical group C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000002530 phenolic antioxidant Substances 0.000 claims abstract description 9
- 229920001059 synthetic polymer Polymers 0.000 claims abstract description 4
- -1 naphtho [2, 3-b] - thienyl Chemical group 0.000 claims description 432
- 239000001257 hydrogen Substances 0.000 claims description 98
- 229910052739 hydrogen Inorganic materials 0.000 claims description 98
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 77
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 66
- 239000001301 oxygen Substances 0.000 claims description 66
- 229910052760 oxygen Inorganic materials 0.000 claims description 66
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims description 52
- 229910052717 sulfur Inorganic materials 0.000 claims description 52
- 239000011593 sulfur Substances 0.000 claims description 52
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 48
- 150000002431 hydrogen Chemical class 0.000 claims description 41
- 125000002947 alkylene group Chemical group 0.000 claims description 40
- 229920001577 copolymer Polymers 0.000 claims description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 19
- 125000001544 thienyl group Chemical group 0.000 claims description 18
- 239000000654 additive Substances 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
- NPDLYUOYAGBHFB-WDSKDSINSA-N Asn-Arg Chemical compound NC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N NPDLYUOYAGBHFB-WDSKDSINSA-N 0.000 claims description 14
- 239000004698 Polyethylene Substances 0.000 claims description 14
- 239000004743 Polypropylene Substances 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 229920000573 polyethylene Polymers 0.000 claims description 14
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 13
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 13
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 12
- 125000001589 carboacyl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- 230000009471 action Effects 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 229920001155 polypropylene Polymers 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 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 9
- 150000001993 dienes Chemical class 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
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 230000007774 longterm Effects 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 125000005561 phenanthryl group Chemical group 0.000 claims description 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 229920001169 thermoplastic Polymers 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 150000005673 monoalkenes Chemical class 0.000 claims description 5
- 125000004957 naphthylene group Chemical group 0.000 claims description 5
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 125000005605 benzo group Chemical group 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 125000003838 furazanyl group Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 3
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 3
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 3
- 125000005954 phenoxathiinyl group Chemical group 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 3
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- ZUNGGJHBMLMRFJ-UHFFFAOYSA-O ethoxy-hydroxy-oxophosphanium Chemical compound CCO[P+](O)=O ZUNGGJHBMLMRFJ-UHFFFAOYSA-O 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims 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 claims description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 125000005650 substituted phenylene group Chemical group 0.000 claims 1
- 229920005615 natural polymer Polymers 0.000 abstract description 2
- 229920003023 plastic Polymers 0.000 abstract description 2
- 239000004033 plastic Substances 0.000 abstract description 2
- 150000003254 radicals Chemical class 0.000 description 65
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 44
- 229920000642 polymer Polymers 0.000 description 24
- 229920001228 polyisocyanate Polymers 0.000 description 21
- 239000005056 polyisocyanate Substances 0.000 description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 20
- 125000003118 aryl group Chemical group 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 125000001931 aliphatic group Chemical group 0.000 description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 15
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 14
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 14
- 239000004952 Polyamide Substances 0.000 description 13
- 229920002647 polyamide Polymers 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 12
- 229920000570 polyether Polymers 0.000 description 12
- 239000007983 Tris buffer Substances 0.000 description 11
- 229920001684 low density polyethylene Polymers 0.000 description 11
- 239000004702 low-density polyethylene Substances 0.000 description 11
- 229920002857 polybutadiene Polymers 0.000 description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 10
- 239000005977 Ethylene Substances 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 239000004814 polyurethane Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 8
- 239000005062 Polybutadiene Substances 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 229920001903 high density polyethylene Polymers 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 8
- 239000004417 polycarbonate Substances 0.000 description 8
- 229920002635 polyurethane Polymers 0.000 description 8
- 238000012545 processing Methods 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 239000007859 condensation product Substances 0.000 description 7
- 125000004956 cyclohexylene group Chemical group 0.000 description 7
- 229920001971 elastomer Polymers 0.000 description 7
- 239000004700 high-density polyethylene Substances 0.000 description 7
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- 229940116351 sebacate Drugs 0.000 description 7
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 230000006641 stabilisation Effects 0.000 description 6
- 238000011105 stabilization Methods 0.000 description 6
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 235000006708 antioxidants Nutrition 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- WTVNFKVGGUWHQC-UHFFFAOYSA-N decane-2,4-dione Chemical compound CCCCCCC(=O)CC(C)=O WTVNFKVGGUWHQC-UHFFFAOYSA-N 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 5
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- 238000012360 testing method Methods 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
- KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 4
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 4
- ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 4
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 229920002396 Polyurea Polymers 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 4
- 239000012964 benzotriazole Substances 0.000 description 4
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- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical class CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- JLEXUIVKURIPFI-UHFFFAOYSA-N tris phosphate Chemical compound OP(O)(O)=O.OCC(N)(CO)CO JLEXUIVKURIPFI-UHFFFAOYSA-N 0.000 description 1
- 229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08K5/1535—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH41097 | 1997-02-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE1011643A3 true BE1011643A3 (fr) | 1999-11-09 |
Family
ID=4186412
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE9800126A BE1011643A3 (fr) | 1997-02-21 | 1998-02-19 | Composition stabilisee, melange de stabilisants, et procede pour stabiliser une matiere organique. |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPH10236988A (enExample) |
| KR (1) | KR100530090B1 (enExample) |
| BE (1) | BE1011643A3 (enExample) |
| DE (1) | DE19806846B4 (enExample) |
| ES (1) | ES2138926B1 (enExample) |
| FR (1) | FR2760005B1 (enExample) |
| GB (1) | GB2322374B (enExample) |
| IT (1) | IT1298273B1 (enExample) |
| NL (1) | NL1008373C2 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6521681B1 (en) * | 1996-07-05 | 2003-02-18 | Ciba Specialty Chemicals Corporation | Phenol-free stabilization of polyolefin fibres |
| GB2343007B (en) | 1998-10-19 | 2001-11-07 | Ciba Sc Holding Ag | Colour photographic material |
| WO2001079340A1 (en) * | 2000-04-13 | 2001-10-25 | 3M Innovative Properties Company | Light stable articles |
| GB0119136D0 (en) * | 2001-08-06 | 2001-09-26 | Clariant Int Ltd | Phenolfree stabilizaton of polyolefins |
| TW593303B (en) * | 2001-09-11 | 2004-06-21 | Ciba Sc Holding Ag | Stabilization of synthetic polymers |
| DE10148702A1 (de) * | 2001-10-02 | 2003-04-10 | Basf Ag | Stabilisatorengemisch und stabilisiete Polyurethane |
| DE10240578A1 (de) * | 2002-08-29 | 2004-03-11 | Basf Ag | Stabilisierte Blockcopolymere aus Styrolmonomer und Dienmonomer |
| DE10250768A1 (de) * | 2002-10-30 | 2004-05-13 | Basf Ag | Mischungen enthaltend phenolische Stabilisatoren |
| WO2004111120A1 (en) * | 2003-06-19 | 2004-12-23 | Basell Poliolefine Italia S.R.L. | Olefin polymers with stabilisers and polyolefin fibres produced therefrom |
| US7611829B2 (en) | 2004-01-30 | 2009-11-03 | Fujifilm Corporation | Silver halide color photographic light-sensitive material and color image-forming method |
| WO2006111492A2 (en) * | 2005-04-19 | 2006-10-26 | Ciba Specialty Chemicals Holding Inc. | Polyether polyols, polyester polyols and polyurethanes of low residual aldehyde content |
| JP5073277B2 (ja) * | 2006-12-07 | 2012-11-14 | 電気化学工業株式会社 | フィルム基材及び粘着テープ |
| US8466096B2 (en) | 2007-04-26 | 2013-06-18 | Afton Chemical Corporation | 1,3,2-dioxaphosphorinane, 2-sulfide derivatives for use as anti-wear additives in lubricant compositions |
| US7855246B2 (en) * | 2007-12-05 | 2010-12-21 | Uponor Innovation Ab | Plastic pipe made of polyolefin |
| CN102603686A (zh) * | 2012-02-01 | 2012-07-25 | 华东理工大学 | 2’位含活泼氢的氢键接受体取代基取代的苯并呋喃酮衍生物及其在聚丙烯中的应用 |
| US9518176B2 (en) * | 2013-06-05 | 2016-12-13 | Gse Environmental, Llc | High temperature geomembrane liners and master batch compositions |
| CN105960432B (zh) * | 2014-02-17 | 2019-02-15 | 巴斯夫欧洲公司 | 作为稳定剂的含磷3-苯基苯并呋喃-2-酮衍生物 |
| KR102377818B1 (ko) | 2014-08-05 | 2022-03-24 | 바스프 에스이 | 안정화제로서의 3-페닐-벤조푸란-2-온 디포스파이트 유도체 |
| GB201907363D0 (en) | 2019-05-24 | 2019-07-10 | Si Group Switzerland Chaa Gmbh | Stabilising composition |
| US11692085B2 (en) * | 2020-03-18 | 2023-07-04 | University Of South Florida | Geomembranes and methods for making and using the same |
| CN112063014A (zh) * | 2020-08-10 | 2020-12-11 | 上海奇克氟硅材料有限公司 | 抗烧芯、抗黄变的抗氧剂组合物及其制备和应用 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4228247A (en) * | 1979-08-29 | 1980-10-14 | Basf Wyandotte Corporation | Stabilized polyoxyalkylene polyether polyol |
| DE3725926A1 (de) * | 1987-08-05 | 1989-02-16 | Basf Ag | Gemisch zum stabilisieren von polyurethanen |
| EP0487077A2 (en) * | 1990-11-22 | 1992-05-27 | Sumitomo Chemical Company, Limited | Cured ethylene.alpha-olefin copolymer-based rubber composition |
| EP0543778A1 (de) * | 1991-11-19 | 1993-05-26 | Ciba-Geigy Ag | Gegen Oxidation bzw. Kernverbräunung geschützte Polyetherpolyol- und Polyurethanzusammensetzungen |
| EP0630916A2 (en) * | 1990-02-27 | 1994-12-28 | Mitsui Petrochemical Industries, Ltd. | Ethylene/pentene-1 copolymer, process for the preparation of the same, and ethylene/pentene-1 copolymer composition |
| EP0643042A1 (de) * | 1993-09-13 | 1995-03-15 | BASF Aktiengesellschaft | Lagerstabile, nach phosgenfreien Verfahren erhältliche Polyisocyanatzusammensetzungen, ein Verfahren zu ihrer Herstellung und ihre Verwendung |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH686306A5 (de) * | 1993-09-17 | 1996-02-29 | Ciba Geigy Ag | 3-Aryl-benzofuranone als Stabilisatoren. |
| FR2725451B1 (fr) * | 1994-10-06 | 1998-04-17 | Sandoz Sa | Nouvelle composition stabilisante pour les matieres polymeres |
| GB2311528A (en) * | 1996-03-29 | 1997-10-01 | Ciba Geigy Ag | Stabiliser mixtures for polyamides, polyesters and polyketones |
| US6521681B1 (en) * | 1996-07-05 | 2003-02-18 | Ciba Specialty Chemicals Corporation | Phenol-free stabilization of polyolefin fibres |
-
1998
- 1998-02-04 GB GB9802277A patent/GB2322374B/en not_active Expired - Fee Related
- 1998-02-18 DE DE1998106846 patent/DE19806846B4/de not_active Expired - Fee Related
- 1998-02-18 IT ITMI980307 patent/IT1298273B1/it active IP Right Grant
- 1998-02-19 FR FR9802002A patent/FR2760005B1/fr not_active Expired - Fee Related
- 1998-02-19 BE BE9800126A patent/BE1011643A3/fr not_active IP Right Cessation
- 1998-02-20 NL NL1008373A patent/NL1008373C2/nl not_active IP Right Cessation
- 1998-02-20 KR KR1019980005266A patent/KR100530090B1/ko not_active Expired - Fee Related
- 1998-02-20 JP JP5591798A patent/JPH10236988A/ja not_active Withdrawn
- 1998-02-20 ES ES9800347A patent/ES2138926B1/es not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4228247A (en) * | 1979-08-29 | 1980-10-14 | Basf Wyandotte Corporation | Stabilized polyoxyalkylene polyether polyol |
| DE3725926A1 (de) * | 1987-08-05 | 1989-02-16 | Basf Ag | Gemisch zum stabilisieren von polyurethanen |
| EP0630916A2 (en) * | 1990-02-27 | 1994-12-28 | Mitsui Petrochemical Industries, Ltd. | Ethylene/pentene-1 copolymer, process for the preparation of the same, and ethylene/pentene-1 copolymer composition |
| EP0487077A2 (en) * | 1990-11-22 | 1992-05-27 | Sumitomo Chemical Company, Limited | Cured ethylene.alpha-olefin copolymer-based rubber composition |
| EP0543778A1 (de) * | 1991-11-19 | 1993-05-26 | Ciba-Geigy Ag | Gegen Oxidation bzw. Kernverbräunung geschützte Polyetherpolyol- und Polyurethanzusammensetzungen |
| EP0643042A1 (de) * | 1993-09-13 | 1995-03-15 | BASF Aktiengesellschaft | Lagerstabile, nach phosgenfreien Verfahren erhältliche Polyisocyanatzusammensetzungen, ein Verfahren zu ihrer Herstellung und ihre Verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| NL1008373C2 (nl) | 1999-04-19 |
| ITMI980307A1 (it) | 1999-08-18 |
| GB9802277D0 (en) | 1998-04-01 |
| GB2322374B (en) | 2001-04-04 |
| KR19980071539A (ko) | 1998-10-26 |
| ES2138926B1 (es) | 2000-09-16 |
| FR2760005A1 (fr) | 1998-08-28 |
| KR100530090B1 (ko) | 2006-02-03 |
| ES2138926A1 (es) | 2000-01-16 |
| FR2760005B1 (fr) | 1999-12-24 |
| NL1008373A1 (nl) | 1998-08-24 |
| JPH10236988A (ja) | 1998-09-08 |
| IT1298273B1 (it) | 1999-12-20 |
| GB2322374A (en) | 1998-08-26 |
| DE19806846B4 (de) | 2007-11-15 |
| DE19806846A1 (de) | 1998-08-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE | Patent lapsed |
Effective date: 20090228 |