CA2132134C - Benzofuran-2-ones as stabilisers - Google Patents
Benzofuran-2-ones as stabilisers Download PDFInfo
- Publication number
- CA2132134C CA2132134C CA002132134A CA2132134A CA2132134C CA 2132134 C CA2132134 C CA 2132134C CA 002132134 A CA002132134 A CA 002132134A CA 2132134 A CA2132134 A CA 2132134A CA 2132134 C CA2132134 C CA 2132134C
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen
- substituted
- c4alkyl
- formula
- hydroxy
- 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.)
- Expired - Fee Related
Links
- 239000003381 stabilizer Substances 0.000 title claims abstract description 17
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 90
- 239000011368 organic material Substances 0.000 claims abstract description 15
- 230000015556 catabolic process Effects 0.000 claims abstract description 10
- 238000006731 degradation reaction Methods 0.000 claims abstract description 10
- 230000001590 oxidative effect Effects 0.000 claims abstract description 9
- -1 chloro, hydroxy Chemical group 0.000 claims description 153
- 239000001257 hydrogen Substances 0.000 claims description 113
- 229910052739 hydrogen Inorganic materials 0.000 claims description 113
- 235000013350 formula milk Nutrition 0.000 claims description 97
- 150000002431 hydrogen Chemical class 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 56
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 34
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 34
- 229910052760 oxygen Inorganic materials 0.000 claims description 34
- 239000001301 oxygen Substances 0.000 claims description 34
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 27
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 27
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 23
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 239000011593 sulfur Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000001038 naphthoyl group Chemical class C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 17
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 16
- 150000001721 carbon Chemical group 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 15
- 150000004820 halides Chemical class 0.000 claims description 15
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 125000000843 phenylene group Chemical class C1(=C(C=CC=C1)*)* 0.000 claims description 13
- 239000004743 Polypropylene Substances 0.000 claims description 12
- 239000000654 additive Substances 0.000 claims description 11
- 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 10
- 239000004698 Polyethylene Substances 0.000 claims description 9
- 125000001246 bromo group Chemical group Br* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 229920000098 polyolefin Polymers 0.000 claims description 8
- 229920001155 polypropylene Polymers 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims description 6
- 229920000573 polyethylene Polymers 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 5
- 230000003019 stabilising effect Effects 0.000 claims description 5
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical group NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 239000002530 phenolic antioxidant Substances 0.000 claims description 4
- 125000002346 iodo group Chemical group I* 0.000 claims description 3
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 239000004611 light stabiliser Substances 0.000 claims description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 2
- 229920001059 synthetic polymer Polymers 0.000 claims description 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 230000000996 additive effect Effects 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 44
- 229920001577 copolymer Polymers 0.000 description 29
- 229940044603 styrene Drugs 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- 150000003254 radicals Chemical class 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 19
- 125000000217 alkyl group Chemical group 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 17
- 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- 229960003742 phenol Drugs 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000005977 Ethylene Substances 0.000 description 12
- 239000004952 Polyamide Substances 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 229920002647 polyamide Polymers 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229910052615 phyllosilicate Inorganic materials 0.000 description 9
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- 239000007983 Tris buffer Substances 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- 229920001684 low density polyethylene Polymers 0.000 description 8
- 239000004702 low-density polyethylene Substances 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 229920002857 polybutadiene Polymers 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 150000002170 ethers Chemical class 0.000 description 7
- 150000002367 halogens Chemical group 0.000 description 7
- 229940059574 pentaerithrityl Drugs 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 150000001993 dienes Chemical class 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 6
- 235000021317 phosphate Nutrition 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 235000012211 aluminium silicate Nutrition 0.000 description 5
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 229920006324 polyoxymethylene Polymers 0.000 description 5
- 229920006380 polyphenylene oxide Polymers 0.000 description 5
- 229920000915 polyvinyl chloride Polymers 0.000 description 5
- 239000004800 polyvinyl chloride Substances 0.000 description 5
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- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
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- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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- 150000001298 alcohols Chemical class 0.000 description 4
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
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- 150000003839 salts Chemical class 0.000 description 3
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- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
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- RNVAPPWJCZTWQL-UHFFFAOYSA-N octadecyl 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 RNVAPPWJCZTWQL-UHFFFAOYSA-N 0.000 description 1
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- 125000002958 pentadecyl 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])[H] 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
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- 229960000969 phenyl salicylate Drugs 0.000 description 1
- ZPNJBTBYIHBSIG-UHFFFAOYSA-N phenyl-(2,2,6,6-tetramethylpiperidin-4-yl)methanone Chemical compound C1C(C)(C)NC(C)(C)CC1C(=O)C1=CC=CC=C1 ZPNJBTBYIHBSIG-UHFFFAOYSA-N 0.000 description 1
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- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 150000003222 pyridines Chemical class 0.000 description 1
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- 239000012744 reinforcing agent Substances 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- IJRHDFLHUATAOS-DPMBMXLASA-M sodium ricinoleate Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O IJRHDFLHUATAOS-DPMBMXLASA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
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- 238000009987 spinning Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
- 125000003696 stearoyl 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])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
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- OHRVKCZTBPSUIK-UHFFFAOYSA-N tridodecyl phosphate Chemical compound CCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCC)OCCCCCCCCCCCC OHRVKCZTBPSUIK-UHFFFAOYSA-N 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- FDGZUBKNYGBWHI-UHFFFAOYSA-N trioctadecyl phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC FDGZUBKNYGBWHI-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- OOZBTDPWFHJVEK-UHFFFAOYSA-N tris(2-nonylphenyl) phosphate Chemical compound CCCCCCCCCC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC OOZBTDPWFHJVEK-UHFFFAOYSA-N 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
- 125000002948 undecyl 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])[H] 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 238000005406 washing Methods 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
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- 229910052726 zirconium Inorganic materials 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
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fireproofing Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Table Devices Or Equipment (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH281193 | 1993-09-17 | ||
| CH2811/93-9 | 1993-09-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2132134A1 CA2132134A1 (en) | 1995-03-18 |
| CA2132134C true CA2132134C (en) | 2006-04-04 |
Family
ID=4242127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002132134A Expired - Fee Related CA2132134C (en) | 1993-09-17 | 1994-09-15 | Benzofuran-2-ones as stabilisers |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US5614572A (cg-RX-API-DMAC10.html) |
| EP (1) | EP0644190B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP3793950B2 (cg-RX-API-DMAC10.html) |
| KR (1) | KR100361629B1 (cg-RX-API-DMAC10.html) |
| CN (1) | CN1052230C (cg-RX-API-DMAC10.html) |
| AT (1) | ATE177740T1 (cg-RX-API-DMAC10.html) |
| BR (1) | BR9403592A (cg-RX-API-DMAC10.html) |
| CA (1) | CA2132134C (cg-RX-API-DMAC10.html) |
| CZ (1) | CZ289139B6 (cg-RX-API-DMAC10.html) |
| DE (1) | DE59407946D1 (cg-RX-API-DMAC10.html) |
| ES (1) | ES2130385T3 (cg-RX-API-DMAC10.html) |
| RU (1) | RU2135489C1 (cg-RX-API-DMAC10.html) |
| SK (1) | SK280591B6 (cg-RX-API-DMAC10.html) |
| TW (1) | TW270133B (cg-RX-API-DMAC10.html) |
| ZA (1) | ZA947184B (cg-RX-API-DMAC10.html) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW270133B (cg-RX-API-DMAC10.html) * | 1993-09-17 | 1996-02-11 | Ciba Geigy | |
| TW416970B (en) * | 1995-05-31 | 2001-01-01 | Ciba Sc Holding Ag | Carrier-bound light stabilizers and antioxidants as fillers and stabilizers |
| EP0839623B1 (de) * | 1996-10-30 | 2001-01-31 | Ciba SC Holding AG | Stabilisatorkombination für das Rotomolding-Verfahren |
| WO1998055543A1 (en) * | 1997-06-05 | 1998-12-10 | Dyneon Llc | Polymer stabilization |
| WO1999003915A1 (en) * | 1997-07-14 | 1999-01-28 | Dover Chemical Corporation | Lactone/phosphite blends |
| EP1015518B1 (en) | 1997-09-10 | 2002-05-15 | Ciba SC Holding AG | Isoxindigos useful as colorants and preparation thereof |
| DE19801462A1 (de) | 1998-01-16 | 1999-07-22 | Basf Ag | Katalysator und Verfahren zur Herstellung von Polytetrahydrofuran |
| AU3521899A (en) | 1998-04-08 | 1999-11-01 | Ciba Specialty Chemicals Holding Inc. | Dibenzonaphthyrones and their use for colouring/pigmenting high-molecular-weightorganic material |
| AU1041800A (en) | 1998-11-02 | 2000-05-22 | Ciba Specialty Chemicals Holding Inc. | Stabilisation of body-care and household products |
| CN1330645C (zh) * | 1999-03-10 | 2007-08-08 | 西巴特殊化学品控股有限公司 | 作为有机材料着色剂的苯并呋喃－2－酮类化合物 |
| US6664317B2 (en) * | 2000-02-18 | 2003-12-16 | Ciba Specialty Chemicals Corporation | Stabilized gamma irradiated polyolefins |
| CN1182127C (zh) * | 2000-06-28 | 2004-12-29 | 中国医学科学院药物研究所 | 新的取代的2-苯并[c]呋喃酮化合物,其制备方法以及包含它们的药物组合物 |
| US6890978B2 (en) * | 2000-08-09 | 2005-05-10 | A&M Styrene Co., Ltd. | Aromatic monovinyl resin composition |
| US6569927B1 (en) | 2000-10-06 | 2003-05-27 | Uniroyal Chemical Company, Inc. | Thermoplastic resins stabilized by blends of sterically hindered phenols, secondary amines, and lactones |
| DE60205734T2 (de) * | 2001-03-20 | 2006-03-09 | Ciba Speciality Chemicals Holding Inc. | Flammhemmende zusammensetzungen |
| TW593303B (en) * | 2001-09-11 | 2004-06-21 | Ciba Sc Holding Ag | Stabilization of synthetic polymers |
| US20080149879A1 (en) * | 2005-02-25 | 2008-06-26 | Fabien Jean Brand | Fluorinated Compounds |
| US20070049666A1 (en) * | 2005-08-30 | 2007-03-01 | James Haworth | Tocopherol compositions and uses |
| CN100345836C (zh) * | 2005-10-17 | 2007-10-31 | 湘潭大学 | 一种苯并呋喃酮类稳定剂及其应用 |
| JP5580985B2 (ja) | 2006-05-01 | 2014-08-27 | 出光興産株式会社 | 光半導体封止材料 |
| US20090155495A1 (en) * | 2006-05-12 | 2009-06-18 | Konica Minolta Opto, Inc. | Process for producing cellulose acylate film, cellulose acylate film, polarizer, and liquid-crystal display |
| EP2167570A1 (en) | 2007-06-29 | 2010-03-31 | Basell Poliolefine Italia S.R.L. | An irradiated polyolefin composition comprising a non - phenolic stabilizer |
| US7988881B2 (en) * | 2008-09-30 | 2011-08-02 | E. I. Du Pont De Nemours And Company | Multilayer laminates comprising chiral nematic liquid crystals |
| WO2010067779A1 (ja) | 2008-12-09 | 2010-06-17 | 出光興産株式会社 | 光学部品用樹脂原料組成物、光学部品用樹脂および光学部品 |
| US8286405B1 (en) * | 2009-08-11 | 2012-10-16 | Agp Plastics, Inc. | Fire and impact resistant window and building structures |
| JP5775525B2 (ja) | 2010-10-25 | 2015-09-09 | 出光興産株式会社 | （メタ）アクリレート系組成物 |
| JP6559224B2 (ja) * | 2014-08-05 | 2019-08-14 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 安定化剤としての３−フェニル−ベンゾフラン−２−オンジホスファイト誘導体 |
| CN117098787A (zh) | 2021-04-07 | 2023-11-21 | 出光兴产株式会社 | 注射成形用热固化性组合物、使用该组合物的成形品的制造方法和固化物 |
| US20240208116A1 (en) | 2021-04-07 | 2024-06-27 | Idemitsu Kosan Co.,Ltd. | Thermosetting composition for injection molding, method for producing molded article using the same, and cured product |
| WO2023068290A1 (ja) * | 2021-10-22 | 2023-04-27 | 三菱瓦斯化学株式会社 | 熱可塑性樹脂組成物、成形体、熱可塑性樹脂組成物の製造方法及び透過率向上方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2042562B (en) * | 1979-02-05 | 1983-05-11 | Sandoz Ltd | Stabilising polymers |
| US5175312A (en) * | 1989-08-31 | 1992-12-29 | Ciba-Geigy Corporation | 3-phenylbenzofuran-2-ones |
| EP0415887B1 (de) * | 1989-08-31 | 1994-10-05 | Ciba-Geigy Ag | 3-Phenylbenzofuran-2-one |
| GB2252325A (en) * | 1991-01-31 | 1992-08-05 | Ciba Geigy Ag | Stabilised polyolefin |
| TW206220B (cg-RX-API-DMAC10.html) * | 1991-07-01 | 1993-05-21 | Ciba Geigy Ag | |
| GB2267490B (en) * | 1992-05-22 | 1995-08-09 | Ciba Geigy Ag | 3-(Carboxymethoxyphenyl)benzofuran-2-one stabilisers |
| CH686306A5 (de) * | 1993-09-17 | 1996-02-29 | Ciba Geigy Ag | 3-Aryl-benzofuranone als Stabilisatoren. |
| TW270133B (cg-RX-API-DMAC10.html) * | 1993-09-17 | 1996-02-11 | Ciba Geigy |
-
1994
- 1994-08-30 TW TW083107936A patent/TW270133B/zh active
- 1994-09-08 AT AT94810520T patent/ATE177740T1/de not_active IP Right Cessation
- 1994-09-08 EP EP94810520A patent/EP0644190B1/de not_active Expired - Lifetime
- 1994-09-08 ES ES94810520T patent/ES2130385T3/es not_active Expired - Lifetime
- 1994-09-08 DE DE59407946T patent/DE59407946D1/de not_active Expired - Lifetime
- 1994-09-12 US US08/304,470 patent/US5614572A/en not_active Expired - Fee Related
- 1994-09-14 KR KR1019940023791A patent/KR100361629B1/ko not_active Expired - Lifetime
- 1994-09-14 JP JP24735594A patent/JP3793950B2/ja not_active Expired - Lifetime
- 1994-09-14 SK SK1103-94A patent/SK280591B6/sk unknown
- 1994-09-15 CA CA002132134A patent/CA2132134C/en not_active Expired - Fee Related
- 1994-09-15 CZ CZ19942261A patent/CZ289139B6/cs not_active IP Right Cessation
- 1994-09-16 BR BR9403592A patent/BR9403592A/pt not_active IP Right Cessation
- 1994-09-16 CN CN94115267A patent/CN1052230C/zh not_active Expired - Lifetime
- 1994-09-16 ZA ZA947184A patent/ZA947184B/xx unknown
- 1994-09-16 RU RU94033474A patent/RU2135489C1/ru not_active IP Right Cessation
-
1996
- 1996-09-17 US US08/715,057 patent/US5693829A/en not_active Expired - Lifetime
-
1997
- 1997-06-25 US US08/881,977 patent/US5807505A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ZA947184B (en) | 1995-03-17 |
| KR950008500A (ko) | 1995-04-17 |
| EP0644190B1 (de) | 1999-03-17 |
| US5693829A (en) | 1997-12-02 |
| CN1052230C (zh) | 2000-05-10 |
| ATE177740T1 (de) | 1999-04-15 |
| DE59407946D1 (de) | 1999-04-22 |
| ES2130385T3 (es) | 1999-07-01 |
| CZ289139B6 (cs) | 2001-11-14 |
| TW270133B (cg-RX-API-DMAC10.html) | 1996-02-11 |
| US5807505A (en) | 1998-09-15 |
| SK280591B6 (sk) | 2000-04-10 |
| CZ226194A3 (en) | 1995-04-12 |
| US5614572A (en) | 1997-03-25 |
| JPH07247278A (ja) | 1995-09-26 |
| BR9403592A (pt) | 1995-05-16 |
| SK110394A3 (en) | 1995-06-07 |
| CA2132134A1 (en) | 1995-03-18 |
| RU2135489C1 (ru) | 1999-08-27 |
| CN1106032A (zh) | 1995-08-02 |
| EP0644190A1 (de) | 1995-03-22 |
| KR100361629B1 (ko) | 2003-02-05 |
| JP3793950B2 (ja) | 2006-07-05 |
| RU94033474A (ru) | 1996-07-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |